SUPPLEMENTARY INFORMATION

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1 doi: /nature22309 Chemistry All reagents and solvents were commercially available unless otherwise noted. Analytical LC-MS was carried out using a Shimadzu LCMS-2020 with UV detection monitored between nm using ESI protocol. The column used was Ascentis express C18 with dimensions of 2.1 mm x 50 mm, 2.7 µm, running at 40 C. The flow rate was 1ml/min using a solvent gradient of 5 to 100% B over 1.8 minutes, where A = water (0.05% TFA) and B = acetonitrile (0.05% TFA). Where indicated the mobile phases were made basic and replaced with A= water +6.5 mm NH 4 HCO 3 to ph10 in A, and B = acetonitrile (no additive). An alternative method was employed for some samples using UPLC-MS, which was carried out using a Waters Acquity UPLC and Waters SQD mass spectrometer. In this system, the UV detection was set = nm and mass spectrometry was done with ESI with positive/negative switching and cone voltage = 10 V. The column used was Waters Acquity HSS T3, 1.8µm, 2.1 x30 mm, at temperature 30 C. The flow rate was 1ml/min using a solvent gradient of 2 to 98% B over 1.5 minutes (total runtime with equilibration back to starting conditions 2 min), where A = 0.1% formic acid in water and B = 0.1% formic acid in acetonitrile. For 1 H NMR and 13 C NMR spectroscopy, the chemical shifts are reported in part-permillion from a tetramethylsilane standard. (R)-(4-fluoro-2-propylphenyl)(1H-imidazol-2-yl)methanol (AZ8838). 2-Bromo-4- fluorobenzaldehyde (5.00 g, 24.6 mmol) was added to propylboronic acid (3.25 g, 36.9 mmol), PdCl 2 (dppf) (1.80 g, 2.46 mmol) and Cs 2 CO 3 (16.0 g, 49.3 mmol) in dioxane (40 ml) and water (10 ml), then warmed to 80 C under nitrogen. The resulting suspension was stirred at 80 C for 12 hours. The reaction mixture was diluted with EtOAc (50 ml), and washed sequentially with an aqueous saturated NaCl solution (20 ml x3). The organic layer was dried over Na 2 SO 4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography with an elution gradient 0 to 5% EtOAc in petroleum ether. Pure fractions were evaporated to dryness to afford 4-fluoro-2- propylbenzaldehyde (3.10 g, 76 %) as a pale yellow liquid. 1 H NMR (400 MHz, DMSO-d 6 ): δ (s, 1H), 7.93 (dd, 1H, J = 8.2, 6.3), (m, 2H), (m, 2H), 1.58 (m, 2H), 0.93 (t, 3H, J = 7.3). In a separate reaction flask, sodium hydride (0.53 g, 22.0 mmol) in THF (50 ml) was cooled to 0 C over a period of 10 minutes under nitrogen. To this was slowly added imidazole (1.00 g, 14.7 mmol) in THF (30 ml) under nitrogen and the temperature was increased to room temperature gradually (caution: exothermic reaction with liberation of gas). The resulting mixture was stirred at 25 C for 30 minutes, and then (2- (chloromethoxy)ethyl)trimethylsilane (3.67 g, 22.0 mmol) was added slowly to the mixture at 0 C over a period of 1 minute under nitrogen. The temperature was increased to room temperature gradually. The resulting mixture was stirred at 25 C for 14 hours. The mixture was concentrated and diluted with EtOAc (200 ml), and washed with water (150 ml). The organic layer was dried over Na 2 SO 4, filtered and evaporated to afford crude product. The crude product was purified by C18-flash chromatography with an elution gradient 0 to 50% MeCN in water. Pure fractions were evaporated to dryness to afford 1-((2- (trimethylsilyl)ethoxy)methyl)-1h-imidazole (2.91 g, 100%) as a white oil which solidified 1

2 RESEARCH SUPPLEMENTARY INFORMATION on standing. 1 H NMR (300 MHz, DMSO-d 6 ): δ (s, 1H), (s, 1H), (s, 1H), (s, 2H), (m, 2H), (m, 2H), (d, 9H, J = 6.9 Hz); LC-MS: m/z (ES+), [M+H]+ = 199; HPLC t R = min. To a stirred solution of 4-fluoro-2-propylbenzaldehyde (0.30 g, 1.82 mmol) in THF (5 ml) at -78 C, was added a mixture of 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole (0.40 g, 2.02 mmol), n-buli (0.26 g, 4.03 mmol) in THF (5 ml) over a period of 1 minute under nitrogen. The resulting solution was stirred at -78 C for 1 hour. The temperature was increased to room temperature over a period of several hours. The reaction mixture was quenched with saturated NH 4 Cl (5 ml), extracted with DCM (3 x 10 ml). The organic layer was dried over Na 2 SO 4, filtered and evaporated to afford a yellow oil. The residue was purified by preparative TLC (EtOAc: petroleum ether = 1: 2), to afford (4-fluoro-2- propylphenyl)(1-((2-(trimethylsilyl)ethoxy)methyl)-1h-imidazol-2-yl)methanol (0.40 g, 54.4 %) as an orange oil. 1 H NMR (300 MHz, CDCl 3 ): δ 7.21 (dd, J = 8.57, 5.93 Hz, 1 H), 7.05 (dd, J = 16.48, 1.41 Hz, 2 H), (m, 2 H), 6.16 (s, 1 H), (m, 2 H), (m, 2 H), (m, 2 H), (m, 2 H), 1.00 (t, J = 7.25 Hz, 3 H), (m, 2 H), (m, 9 H); LC-MS: m/z (ES+), [M+H]+ = 365; HPLC t R = min. To a solution of (4-fluoro-2-propylphenyl)(1-((2-(trimethylsilyl)ethoxy)methyl)-1Himidazol-2-yl)methanol (11.6 g, mmol) in DCM (50 ml) was added TFA (24.5 ml, 318 mmol). The resulting solution was refluxed for 3 hrs and evaporated. The residue was redissolved in DCM (50 ml) and the solution was treated with saturated NaHCO 3. The precipitate was filtered and dried under vacuum to give (4-fluoro-2-propylphenyl)(1Himidazol-2-yl)methanol (5.88 g, 79 %) as an off-white solid. 1 H NMR (300 MHz, DMSOd 6 ): δ (br. s., 1H) 7.51 (dd, J = 8.57, 6.31 Hz, 1H), (m, 4H), 6.00 (d, J = 4.33 Hz, 1H), 5.90 (d, J = 4.33 Hz, 1H), (m, 1H), (m, 1H), (m, 2H), 0.90 (t, J =7.25 Hz, 3H); UPLC-MS: m/z (ES+), [M+H]+ = 235; TFA, HPLC t R = 0.57 min. The racemic material was separated by chiral SFC using a chiralpak AD-H column (30 x 250 mm, 5 µm). The mobile phase A was supercritical CO 2, and Mobile phase B was isopropanol containing 0.1% dimethylamine. A gradient of up to 15% B was run at 2.8 ml/min and two peaks were isolated to give (R)-(4-fluoro-2-propylphenyl)(1H-imidazol-2-yl)methanol (Peak 1 at 3.25 min, g, 33.4 % and > 99%ee, and (S)-(4-fluoro-2-propylphenyl)(1H-imidazol- 2-yl)methanol (Peak 2 at 4.54 min, g, 33.3 % and >99%ee, as white solids. Absolute stereochemistry was assigned based on a crystal structure of the compound with PAR2 receptor. Analytical data for (S)-(4-fluoro-2-propylphenyl)(1H-imidazol-2-yl)methanol: 1 H NMR (400 MHz, DMSO-d 6 ): δ (br. s., 0.5H), 7.49 (dd, J = 8.6, 6.3 Hz, 1H), (m, 4H), 6.85 (br. s., 1H), 6.06 (br. s., 0.5H), 5.88 (s, 1H), (m, 1H), (m, 1H), (m, 2H), 0.87 (t, J =7.25 Hz, 3H); 13 C NMR (100 MHz, DMSO-d 6 ): δ 162.8, 160.4, 150.2, (d, 3 J CF = 6.9 Hz), 137.6, (d, 3 J CF = 6.9 Hz), (d, 1 J CF = 1111 Hz), (d, 2 J CF = 20.7 Hz), (d, 2 J CF = 20.7 Hz), 66.2, 34.1, 23.9, 14.4; HPLC-MS (m/z) [M+H]+ = 235; HPLC t R = 0.57 min; chiral SFC t R = 3.25 min; HRMS (m/z) [M+] calcd for C 13 H 16 FN 2 O; , found

3 RESEARCH (S)-2-(6-bromobenzo[d][1,3]dioxol-5-yl)-N-(4-cyanophenyl)-1-(1-cyclohexylethyl)-1Hbenzo[d]imidazole-5-carboxamide (AZ3451). Cs 2 CO 3 (16.3 g, 50.2 mmol) was added to methyl 4-fluoro-3-nitrobenzoate (5.00 g, 25.1 mmol) and (S)-1-cyclohexylethanamine (4.79 g, 37.6 mmol) in DMF (8 ml) which was cooled to 0 C under nitrogen. The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with EtOAc (20 ml), and washed sequentially with saturated NH 4 Cl (15 ml x 2). The aqueous layers were combined and washed with EtOAc (2 x 15 ml). The organic layers were dried Na 2 SO 4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography with an elution gradient 0 to 1% EtOAc in petroleum ether. Pure fractions were evaporated to dryness to afford (S)-methyl 4-((1-cyclohexylethyl)amino)-3- nitrobenzoate (7.00 g, 91 %) as a yellow oil which solidified on standing. 1 H NMR (400 MHz, DMSO-d 6 ): δ 8.63 (d, 1H), 8.35 (d, 1H), 7.96 (dd, 1H), 7.23 (d, 1H), 3.83 (s, 5H), 1.75 (m, 5H), 1.57 (m, 3H), 1.14 (m, 11H), 0.84 (m, 1H); HPLC-MS (m/z) [M+H]+ = ; HPLC t R = min. Excess H 2 was added slowly to a stirred solution of Pd/C (1.21 g, 11.4 mmol) and (S)-methyl 4-((1-cyclohexylethyl)amino)-3-nitrobenzoate (7.00 g, 22.8 mmol) in EtOAc/MeOH (40 ml of a 1:1 mixture). The resulting mixture was stirred at room temperature for 4 hours, and then filtered through a pad of diatomaceous earth. The solvent was removed under reduced pressure to afford (S)-methyl 3-amino-4-((1-cyclohexylethyl)amino)benzoate (6.10 g, 96 %) as a green solid. The product was used in the next step directly without further purification. 1 H NMR (400 MHz, DMSO-d 6 ) δ 7.18 (m, 2H), 6.42 (d, 1H), 4.85 (m, 1H), 4.79 (s, 2H), 4.04 (m, 1H), 3.72 (s, 3H), 3.38 (m, 1H), 2.00 (s, 1H), 1.82 (d, 1H), 1.72 (m, 3H), 1.62 (m, 1H), 1.46 (m, 1H), 1.13 (m, 9H); HPLC-MS (m/z) [M+H]+ = ; HPLC t R = min. Iodine (2.72 g, 10.7 mmol) was added to sodium hydroxide (2.14 g, 53.5 mmol), 6- bromobenzo[d][1,3]dioxole-5-carbaldehyde (1.22 g, 5.35 mmol) and methyl (S)-3-amino-4- ((1-cyclohexylethyl)amino)benzoate (1.48 g, 5.35 mmol) in acetonitrile (15 ml) under nitrogen. The resulting mixture was stirred at room temperature for 60 minutes. The reaction mixture was acidified with 2M HCl to ph~3. The reaction mixture was then concentrated and diluted with EtOAc (50 ml), and washed sequentially with water (25 ml x 3), and saturated brine (15 ml x 3). The organic layer was dried over Na 2 SO 4, filtered and evaporated to afford crude product. The crude product was purified by flash C18-flash chromatography, elution gradient 0 to 100% MeCN in water. Pure fractions were evaporated to dryness to afford (S)-2-(6-bromobenzo[d][1,3]dioxol-5-yl)-1-(1-cyclohexylethyl)-1Hbenzo[d]imidazole-5-carboxylic acid (1.90 g, 75 %) as a brown solid. 1 H NMR (300 MHz, DMSO-d 6 ): δ (s, 1H), 8.24 (m, 1H), 7.87 (d, 2H), 7.43 (d, 1H), 7.10 (s, 1H), 6.22 (m, 2H), 4.02 (q, 1H), 3.74 (ddd, 1H), 1.98 (s, 2H), 1.87 (d, 1H), 1.64 (dd, 4H), 1.48 (d, 2H), 1.17 (t, 2H), 0.99 (s, 2H), 0.85 (s, 2H), 0.56 (d, 1H); HPLC-MS (m/z) [M+H]+ = ; HPLC t R = min. To a stirred solution of (S)-2-(6-bromobenzo[d][1,3]dioxol-5-yl)-1-(1-cyclohexylethyl)-1Hbenzo[d]imidazole-5-carboxylic acid (0.080 g, 0.17 mmol) in DCM (2 ml) were added HATU (0.129 g, 0.34 mmol) and then 4-aminobenzonitrile (0.03 g, 0.25 mmol) and N-ethyl- N-isopropylpropan-2-amine (0.044 g, 0.34 mmol). The reaction mixture was stirred at room temperature for 16 hrs, and then heated at 40 C for 6 hrs. The DCM was removed by 3

4 RESEARCH SUPPLEMENTARY INFORMATION vacuum, then 1.5 ml of DMF was added. The reaction mixture was heated at 80 C for 3 hrs and then EtOAc was added (30 ml). This solution was washed with water (3 x 30 ml), brine (30 ml), dried over Na 2 SO 4, filtered and concentrated. The residue was purified with flash chromatography (SiO 2 ), hexanes/etoac) to give off-white solid. 1 H NMR (400 MHz, DMSO-d 6 ): δ (br. s., 1H), (m, 1H), (m, 2H), (m, 1H), (m, 3H), (m, 2H), (m, 1H), (m, 1H), (m, 1H), 1.69 (d, J = 7.0 Hz, 3H), (m, 1H), (m, 2H), (m, 1H), (m, 4H), (m, 1H); 13 C NMR (100 MHz, DMSO-d 6 ): δ 167.0, 154.5, 150.2, 147.6, 144.3, 135.5, 133.5, 128.6, 125.2, 122.9, 120.5, 120.0, 119.6, 115.1, 113.1, 112.8, 112.5, 105.5, 103.2, 58.8, 41.7, 30.3, 25.9, 25.8, 18.0, 17.7; UPLC-MS (m/z) [M+H]+ = 570.1; HPLC t R = 1.37 min. HRMS (m/z) [M+] calcd for C 30 H 28 BrN 4 O 3 ; , found ,3-Dihydro-1H,1'H-2,3'-biindole-1-carbaldehyde (AZ7188). 1H-Indole (5.00 g, 42.6 mmol) was added portionwise to HCl in toluene (107 ml, 213 mmol) in 0 C under nitrogen. The resulting mixture was stirred at 0 C for 3 hours. The reaction mixture was filtered through diatomaceous earth, and then diluted with DCM. The reaction mixture was adjusted to basic ph with saturated NaHCO 3. The organic layers were combined and washed with water (3 x 50 ml) to afford 3-(indolin-2-yl)-1H-indole (4.00g, 40% ) as a pink solid. 1 H NMR (300 MHz, DMSO-d 6 ): δ (m, 1H), (m, 1H), (m, 9H), (m, 1H), (m, 1H), (m, 1 H). HPLC-MS (m/z) [M+H]+ = 235.4; HPLC t R = min; EDC (2.97 g, 15.5 mmol) was added portionwise to formic acid (0.74 ml, 19.4 mmol) and 3- (indolin-2-yl)-1h-indole (2.27g, 9.69 mmol), Et 3 N (4.05 ml, mmol) in DCM (40 ml) at 0 C under nitrogen. The resulting mixture was stirred at 0 C for 4 hours. The reaction mixture was diluted with DCM. The organic layers were combined and washed with water (5 x 75 ml), and then the solvent was removed under reduced pressure. The crude product was purified by flash silica chromatography with an elution gradient 0 to 25 % EtOAc in petroleum ether. Pure fractions were evaporated to dryness to afford 2-(1H-indol-3- yl)indoline-1-carbaldehyde (1.10 g, 43.3 %) as a purple solid. Atropisomers observed in NMR spectra; 1 H NMR (500 MHz, DMSO-d 6, 27 C): δ (s, 1H), (s, 0H), 9.02 (d, J = 1.0 Hz, 0H), 8.31 (s, 1H), (m, 1H), 7.47 (d, J = 8.0 Hz, 0H), (m, 1H), (m, 2H), (m, 1H), 7.19 (d, J = 8.0 Hz, 0H), (m, 3H), 6.88 (dddd, J = 1.0, 7.0, 8.0, 12.0 Hz, 1H), 5.83 (td, J = 6.4, 10.1, 10.6 Hz, 1H), 3.69 (dd, J = 10.1, 16.5 Hz, 1H), 3.25 (dd, J = 5.5, 16.5 Hz, 1H), 3.07 (dd, J = 2.8, 16.4 Hz, 0H); 1 H NMR (500 MHz, DMSO-d 6, 100 C): δ (s, 1H), 8.54 (s, 1H), 7.84 (s, 1H), (m, 1H), (m, 1H), (m, 3H), (m, 2H), 6.91 (ddd, J = 1.0, 7.0, 8.0 Hz, 1H), 5.84 (dd, J = 4.7, 10.0 Hz, 1H), 3.70 (ddt, J = 1.1, 9.9, 16.3 Hz, 1H), (m, 1H); 13 C NMR (100 MHz, DMSO-d 6 ): δ 161.1, 158.9, 141.7, 141.6, 137.4, 137.1, 131.5, 131.3, 128.0, 127.8, 126.3, 125.5, 125.0, 124.8, 124.7, 124.4, 123.4, 122.0, 121.6, 119.5, 119.1, 118.9, 116.3, 115.6, 112.5, 112.1, 110.6, 56.2, 53.9, 36.4; HPLC-MS (m/z) [M+H]+ = 263.0; HPLC t R = min; HRMS (m/z) [M+] calcd for C 17 H 15 N 2 O; , found

5 RESEARCH Abbreviations DCM = dichloromethane DMF = dimethylformamide DMSO = dimethylsulfoxide EDC = 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide EtOAc = ethyl acetate Et 3 N = triethylamine HATU = (1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate) HPLC t R = retention time on high pressure liquid chromatography LC-MS = liquid chromatography mass spectrometry MeCN = acetonitrile MeOH = methanol TLC = thin layer chromatography UPLC-MS = ultra performance liquid chromatography mass spectrometry 5

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