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1 SUPPORTING INFORMATION FOR nbu 4 NI-catalyzed C3-formylation of indoles with N-methylaniline Lan-Tao Li, Juan Huang, Hong-Ying Li, Li-Juan Wen, Peng Wang and Bin Wang College of Pharmacy, State Key Laboratory of Medicinal Chemical Biology and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, 94 Weijin Road, Tianjin , China. Corresponding author: Bin Wang wangbin@nankai.edu.cn Table of Contents 1. General experimental methods 2. General procedure for the nbu 4 NI-catalyzed formylation of indoles with N-methylaniline 3. Optimization of reaction conditions 4. Preparation of 3-formylindole with compound 5 5. The characterization of the products 6. 1 H and 13 C NMR charts of the products 7. References 1
2 1. General experimental methods 1 H NMR and 13 C NMR spectra were recorded on a Bruker AVANCE AV400 (400MHz and 100MHz). Signal positions were recorded in ppm with the abbreviations s, d, t, m and b denoting singlet, doublet, triplet, multiplet and broadened respectively. All NMR chemical shifts were referenced to residual solvent peaks or to Si(CH3) 4 as an internal standard, spectra recorded in CDCl 3 were referenced to residual CHCl 3 at 7.26 ppm for 1 H or 77.0 ppm for 13 C, spectra recorded in CD 3 OD were referenced to residual CD 2 HOD at 3.31 ppm for 1 H or ppm for 13 C, spectra recorded in (CD 3 ) 2 SO were referenced to residual (CD 2 H)SO(CD 3 )at 2.50 ppm for 1 H or ppm for 13 C. All coupling constants J were quoted in Hz. Data were reported as follows: chemical shift, multiplicity, coupling constant and integration. Reactions were monitored by thin-layer chromatography (TLC) on 0.25mm silica gel glass plates coated with 60 F 254. Column chromatography was performed on silica gel ( mesh) using a mixture of petroleum ether (60-90 C)/ethyl acetate as eluant. Reactions were carried out under a nitrogen atmosphere. Commercially available reagents were used as received without purification. 2. General procedure for the Bu 4 NI-catalyzed formylation of indoles with N-methylaniline To a mixture of indole (0.5 mmol, 1 equiv), PivOH (255.3 mg, 2.5 mmol, 5 equiv), and nbuni (18.5 mg, 0.05 mmol, 0.1 equiv) in a 50 ml Schlenk tube were added DMSO (1 ml) under N 2. Then N-methylaniline (107 µl, 1.0 mmol, 2 equiv) and TBPB (373 µl, 2.0 mmol, 4 equiv) were added separately. The mixture was stirred at 80 C for 8h, quenched with saturated NaHCO 3 solution (10 ml). The mixture was extracted by ethyl acetate for 3 times. The combined organic phase was washed with brine and dried with anhydrous Na 2 SO 4, filtrated, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the formylation products. 2
3 3. Optimization of reaction conditions a entry a 1a (mmol) 2a (mmol) catalyst (mmol) oxidant (mmol) Yield (%) nbu 4 NCl (0.05) TBPB (2) 37 b nbu 4 NBr (0.05) TBPB (2) 29 b nbu 4 NI (0.05) TBHP(2) c nbu 4 NI (0.05) IBX (2) trace nbu 4 NI (0.05) NBS (2) trace nbu 4 NI (0.05) NIS (2) nbu 4 NI (0.05) PhI(OAc) 2 (2) trace nbu 4 NI (0.05) Oxone (2) nbu 4 NI (0.05) K 2 S 2 O 8 (2) nbu 4 NI (0.05) m-cpba (2) nbu 4 NI (0.05) p-bq (2) nbu 4 NI(0.05) DDQ (2) 0 a general reaction conditions: to a mixture of indole (0.5mmol), catalyst (0.05mmol), PivOH (2.5mmol), oxidant (2mmol) in a schlank tube was added DMSO (1mL) under N 2. N-methylaniline (1.0mmol) was added, then the mixture was heated at 80 C for 8h. b GC yield. c solution of TBHP in decane ( M) was used. 3
4 4. Preparation of 3-formylindole with compound 5 To a mixture of compound 5 (0.5 mmol, 1 equiv), PivOH (255.3 mg, 2.5 mmol, 5 equiv), and nbuni (18.5 mg, 0.05 mmol, 0.1 equiv) in a 50 ml Schlenk tube were added DMSO (1 ml) under N 2. Then TBPB (373 µl, 2.0 mmol, 4 equiv) were added separately. The mixture was stirred at 80 C for 8h, quenched with saturated NaHCO 3 solution (10 ml). The mixture was extracted by ethyl acetate for 3 times. The combined organic phase was washed with brine and dried with anhydrous Na 2 SO 4, filtrated, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the formylation product 3a in 70% yield. 4
5 5. The characterization of the products 3a 1 1 H-NMR (DMSO-d 6, 400MHz): 12.1 (b, 1H), 9.94(s, 1H), 8.29(s, 1H), 8.10(d, 7.2Hz, 1H), 7.51(d, 8.0Hz, 1H), (m, 2H) 13 C-NMR (DMSO-d 6, 100MHz): , , , , , , , , b 1 1 H-NMR (DMSO-d 6, 400MHz): 12.2(b, 1H), 9.92(s, 1H), 8.35(d, 3.2Hz, 1H), 7.76(dd, 2.4Hz, 9.6Hz, 1H), 7.53(dd, 4.8Hz, 8.8Hz, 1H), 7.11(td, 2.8Hz, 9.2Hz, 1H) 13 C-NMR (DMSO-d 6, 100MHz): , (239.6Hz), , , (7Hz), , (9.5Hz), (25.8Hz), (24.3Hz) 3c 1 1 H-NMR (DMSO-d 6, 400MHz): 12.3(b, 1H), 9.93(s, 1H), 8.36(d, 3.2Hz, 1H), 8.06(d, 2.2Hz, 1H), 7.54(d, 8.4Hz, 1H), 7.28(dd, 2.2Hz, 8.6Hz, 1H) 13 C-NMR (DMSO-d 6, 100MHz): , , , , , , , , d 2 1 H-NMR (CD 3 OD, 400MHz): 9.86(s, 1H), 8.05(s, 1H), 7.99(d, 8.0Hz, 1H), 7.16(t, 7.6Hz, 1H), 7.09(d, 7.2Hz, 1H), 2.90(q, 7.6Hz, 2H), 1.31(t, 7.6Hz, 3H) 13 C-NMR (CD 3 OD, 100MHz): , , , , , , , , , 25.21, H-NMR (DMSO-d 6, 400MHz): 12.1(b, 1H), 9.93(s, 1H), 8.27(d, 3.2Hz, 1H), 7.93(d, 7.6Hz, 1H), 7.15(t, 7.6Hz, 1H), 7.08(d, 7.2Hz, 1H), 2.89(t, 7.4Hz, 2H), 1.26(t, 7.4Hz, 3H) 13 C-NMR (DMSO-d 6, 100MHz): , , , , , , 5
6 122.25, , , 23.52, e 3 1 H-NMR (DMSO-d 6, 400MHz): 12.2(b, 1H), 9.93(s, 1H), 8.32(d, 3.2Hz, 1H), 8.02(d, 8.4Hz, 1H), 7.71(d, 1.6Hz, 1H), 7.36(dd, 1.6Hz, 8.4Hz, 1H) 13 C-NMR (DMSO-d 6, 100MHz): , , , , , , , , f 1 1 H-NMR (DMSO-d 6, 400MHz): 12.3(b, 1H), 9.91(s, 1H), 8.43(d, 1.6Hz, 1H), 8.30(d, 3.2Hz, 1H), 7.54(dd, 1.6Hz, 8.6Hz, 1H), 7.37(d, 8.4Hz, 1H) 13 C-NMR (DMSO-d 6, 100MHz): , , , , , , , , g 1 1 H-NMR (CD 3 OD, 400MHz): 10.0(s, 1H), 8.09(d, 7.2Hz, 1H), 7.34(d, 7.2Hz, 1H), 7.18(t, 4.4Hz, 2H), 2.70(s, 3H) 13 C-NMR (CD 3 OD, 100MHz): , , , , , , , , , h 4 1 H-NMR (DMSO-d 6, 400MHz): 12.3(b, 1H), 9.93(s, 1H), 8.19(d, 3.2Hz, 1H), 7.67(d, 7.6Hz, 1H), 7.57(d, 7.2Hz, 2H), 7.42(t, 7.4Hz, 2H), 7.35(d, 7.2Hz, 1H), 7.12(t, 8.0Hz, 1H), 6.93(d, 8.0Hz, 1H), 5.29(s, 2H) 13 C-NMR (DMSO-d 6, 100MHz): , , , , , , , , , , , , ,
7 3i 1 1 H-NMR (DMSO-d 6, 400MHz): 12.6(b, 1H), 10.00(s, 1H), 8.55(d, 3.2Hz, 1H), 8.24(d, 8.0Hz, 1H), 8.04(s, 1H), 7.59(dd, 1.4Hz, 8.2Hz, 1H) 13 C-NMR (DMSO-d 6, 100MHz): , , , , , , , , , j 1 1 H-NMR (DMSO-d 6, 400MHz): 12.0(b, 1H), 9.89(s, 1H), 8.21(d, 3.2Hz, 1H), 7.58(d, 2.8Hz, 1H), 7.40(d, 8.8Hz, 1H), 6.88(dd, 2.4Hz, 8.8Hz, 1H), 3.78(s, 3H) 13 C-NMR (DMSO-d 6, 100MHz): , , , , , , , , , k 1 1 H-NMR (DMSO-d 6, 400MHz): 12.4(b, 1H), 9.98(s, 1H), 8.50(d, 3.2Hz, 1H), 8.18(d, 8.4Hz, 1H), 8.14(s, 1H), 7.83(d, 8.4Hz, 1H), 3.87(s, 3H) 13 C-NMR (DMSO-d 6, 100MHz): , , , , , , , , , , l 1 1 H-NMR (CD 3 OD, 400MHz):9.86(s, 1H), 8.06(s, 1H), 7.98(d, 7.6Hz, 1H), 7.13(t, 7.4Hz, 1H), 7.06(d, 7.2Hz, 1H), 2.51(s, 3H) 13 C-NMR (CD 3 OD, 100MHz): , , , , , , , , , H-NMR (DMSO-d 6, 400MHz): 12.2(b, 1H), 9.95(s, 1H), 8.29(d, 3.2Hz, 1H), 7.93(d, 7.6Hz, 1H), 7.13(t, 7.6Hz, 1H), 7.06(d, 7.2Hz, 1H), 2.50(s, 3H) 13 C-NMR (DMSO-d 6, 100MHz): , , , , , , , , ,
8 3m 1 1 H-NMR (DMSO-d 6, 400MHz): 12.3(b, 1H), 9.93(s, 1H), 8.34(d, 3.2Hz, 1H), 8.22(d, 1.6Hz, 1H), 7.49(d, 8.4Hz, 1H), 7.39(dd, 2.0Hz, 8.8Hz, 1H) 13 C-NMR (DMSO-d 6, 100MHz): , , , , , , , , n 5 1 H-NMR (CDCl 3, 400MHz): 9.99(s, 1H), 8.33(d, 6.4Hz, 1H), 7.66(s, 1H), 7.37(s, 3H), 3.86(s, 3H) 13 C-NMR (CDCl 3, 100MHz): , , , , , , , , , o 6 1 H-NMR (DMSO-d 6, 400MHz): 9.94(s, 1H), 8.48(s, 1H), 8.12(d, 6.8Hz, 1H), 7.59(d, 8.0Hz, 1H), (m, 7H), 5.55(s, 2H) 13 C-NMR (DMSO-d 6, 100MHz): , , , , , , , , , , , , , p 7 1 H-NMR (DMSO-d 6, 400MHz): 10.0(s, 1H), 8.61(s, 1H), (m, 1H), (m, 4H), (m, 2H), (m, 2H) 13 C-NMR (DMSO-d 6, 100MHz): , , , , , , , , , , , ,
9 3q 8 1 H-NMR (CDCl 3, 400MHz): 10.1(s, 1H), (m, 2H), 7.95(s, 1H), (m, 2H), 7.70(t, 7.4Hz, 1H), 7.60(t, 7.6Hz, 2H), (m, 2H) 13 C-NMR (CDCl 3, 100MHz): , , , , , , , , , , , , H-NMR (CDCl 3, 400MHz): 7.06 (d, 8.4Hz, 2H), 6.71(d, 5.6Hz, 2H), 3.81(s, 2H), 2.91(s, 12H) 13 C-NMR (CDCl 3, 100MHz): , , 40.97, H and 13 C NMR charts of the products 3a 9
10 3b 10
11 3c 11
12 3d in methanol-d 4 12
13 3d in DMSO-d 6 13
14 3e 14
15 3f 15
16 3g in methanol-d 4 16
17 3h 17
18 18
19 3i 19
20 3j 20
21 3k 21
22 3l in methanol-d 4 22
23 3l in DMSO-d 6 23
24 24
25 3m 25
26 3n 26
27 3o 27
28 3p 28
29 3q 29
30 30
31 4 31
32 7. References 1. W. Wu and W. Su, J. Am. Chem. Soc., 2011, 133, S.-C. Lin, F.-D. Yang, J.-S. Shiue, S.-M. Yang and J.-M. Fang, J. Org. Chem., 1998, 63, D. F. Cummings, D. C. Canseco, P. Sheth, J. E. Johnson and J. A. Schetz, Bioorg. Med. Chem., 2010, 18, H. Ueda, H. Satoh, K. Matsumoto, K. Sugimoto, T. Fukuyama and H. Tokuyama, Angew. Chem. Int. Ed., 2009, 48, M. G. Bursavich, N. Brooijmans, L. Feldberg, I. Hollander, S. Kim, S. Lombardi, K. Park, R. Mallon and A. M. Gilbert, Bioorg. Med. Chem. Lett., 2010, 20, N. R. Penthala, T. R. Yerramreddy and P. A. Crooks, Bioorg. Med. Chem. Lett., 2011, 21, C. Sagnes, G. Fournet and B. Joseph, Synlett, 2009, R. Aggarwal, F. Benedetti, F. Berti, S. Buchini, A. Colombatti, F. Dinon, V. Galasso and S. Norbedo, Chem. Eur. J., 2003, 9, S. Murata, M. Miura and M. Nomura, J. Org. Chem., 1989, 54,
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Supplementary Method Synthesis of 2-alkyl-MPT(R) General information (R) enantiomer of 2-alkyl (18:1) MPT (hereafter designated as 2-alkyl- MPT(R)), was synthesized as previously described 1, with some