Cara E. Brocklehurst, Fabrice Gallou, J. Constanze D. Müller-Hartwieg, Marco Palmieriand Dominik Rufle
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1 Supporting information for: Microtiter Plate (MTP) Reaction Screening and Optimization of Surfactant Chemistry: Examples of Suzuki-Miyaura and Buchwald-Hartwig Cross-Couplings in Water Cara E. Brocklehurst, Fabrice Gallou, J. Constanze D. Müller-Hartwieg, Marco Palmieriand Dominik Rufle Equipment and MPT design Liquid handling was performed using an Eppendorf EP Motion which has been shown to accurately pipette down to 1 µl volumes. Liquids can be transferred either with single tips or with the 8 channel pipette for rapid plate preparation. The pre-catalysts were dissolved in THF and pipetted across to plastic MTP s. The THF was evaporated before blanketing under argon and sealing for storage in the fridge; a method which allowed preparation of multiple plates at a time. The plate layout is shown in Table S1 and was applied to both Suzuki-Miyaura and Buchwald-Hartwig screens for convenience. The reactions contain 20 mol % catalyst and 5 eq of base BrettPhos-Pd-G3 RuPhos-Pd-G3 SPhos-Pd-G3 XantPhos-Pd-G3 Pd-PEPPSI-iPr Pd-PEPPSI-iPent XPhos-Pd-G3 AmPhos-Pd-G3 tbuxphos-pd-g3 DavePhos-Pd-G3 P(Cy)3-Pd-G3 Pd(dtbpf) Cl2 A Sol 1 Base 1 B Sol 1 Base 2 C Sol 1 Base 3 D Sol 1 Base 4 E Sol 2 Base 1 F Sol 2 Base 2 G Sol 2 Base 3 H Sol 2 Base 4 Table S1: MTP layout
2 Suzuki-Miyaura Screen Stock solution A: 2-Bromo-3-fluoroaniline (45.6 mg, 0.24 mmol) and 2-(2-(1,1-difluoroethyl)-4- fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (89 mg, 0.31 mmol) were dissolved in THF (1200 µl) to give a clear solution (sufficient material for 120 wells, of which 96 will be used) All wells were filled with 10 µl of SM stock solution A (containing 2 µmol 2-bromo-3-fluoroaniline and 2.6 µmol 2-(2-(1,1-difluoroethyl)-4-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane). The THF was evaporated in the drying oven at room temperature and full vacuum for 30 minutes and then expanded with argon. Stock solution B: 6.25 % PEG in 2% aq TPGS-750-M (2400 µl) degassed Stock solution C: 6.25 % THF in 2% aq TPGS-750-M (2400 µl) degassed Rows A1-D12 (48 wells) were filled with 40 µl of stock solution B and rows E1-H12 (48 wells) were filled with 40 µl of stock solution C Stock solution D: Cs 2 CO 3 1M aq (250 µl) Stock solution E: Et 3 N neat (immiscible with water) (250 µl) Stock solution F: K 3 PO 4 1M aq (250 µl) Stock solution G: Na 2 CO 3 1M aq (250 µl) Rows A1-A12 and E1-E12 were filled with 10 µl of stock solution D; Rows B1-B12 and F1-F12 were filled with 1.3 µl of Et 3 N and 8.7 µl water (stock solution E); Rows C1-C12 and G1-G12 were filled with 10 µl of stock solution F; Rows D1-D12 and H1-H12 were filled with 10 µl of stock solution G. After the pipetting, the plate was flushed again with argon (with low pressure to avoid evaporation of the co-solvent) and sealed with self-glueing PP-foil. The loaded and sealed MTP was shaken overnight at 40 C and 900 RPM. The finished reaction was diluted for analysis by UPLC-MS. The sealing was opened carefully and each well diluted with 150 µl MeCN/H 2 O (9:1) and mixed 8 times by the robot in the pipette tips (with aspirating/dispensing). For each well, 40 µl of the quenched reaction solution was pipetted into a new analytical MTP with the same coordinates. To each well was added 160 µl MeCN/H 2 O (9:1) and mixed 6 times in the tips. The analytical MTP sealed with self-adhesive PP-foil and run over night the UPLC-MS Results visualised in heat map (see main paper) or 3D plot of the MTP (see Figure S1) in which peak area from HPLC is plotted against the plate positions.
3 Figure S1: 3D plot of the MTP of peak area from HPLC plotted against plate position A1-H12
4 Buchwald-Hartwig Screen Stock solution A: 8-Bromo-1,6-naphthyridine (50.2 mg, 0.24 mmol) and tert-butyl carbamate (56 mg, 0.48 mmol) were dissolved in THF (1200 µl) to give a clear solution (sufficient material for 120 wells, of which 96 will be used) All wells were filled with 10 µl of SM stock solution A (containing 2 µmol 8-bromo-1,6-naphthyridine and 4 µmol tert-butyl carbamate). The THF was evaporated in the drying oven at room temperature and full vacuum for 30 minutes and then expanded with argon. Stock solution B: 12.5 % acetone in 2% aq TPGS-750-M (2400 µl) degassed Stock solution C: 12.5 % THF in 2% aq TPGS-750-M (2400 µl) degassed Rows A1-D12 (48 wells) were filled with 40 µl of stock solution B and rows E1-H12 (48 wells) were filled with 40 µl of stock solution C Stock solution D: Cs 2 CO 3 1M aq (250 µl) Stock solution E: Et 3 N neat (immiscible with water) (250 µl) Stock solution F: K 3 PO 4 1M aq (250 µl) Stock solution G: Na 2 CO 3 1M aq (250 µl) Rows A1-A12 and E1-E12 were filled with 10 µl of stock solution D; Rows B1-B12 and F1-F12 were filled with 1.3 µl of Et 3 N and 8.7 µl water (stock solution E); Rows C1-C12 and G1-G12 were filled with 10 µl of stock solution F; Rows D1-D12 and H1-H12 were filled with 10 µl of stock solution G. After the pipetting, the plate was flushed again with argon (with low pressure to avoid evaporation of the co-solvent) and sealed with self-glueing PP-foil. The loaded and sealed MTP was shaken overnight at 40 C and 900 RPM. The finished reaction was diluted for analysis by UPLC-MS. The sealing was opened carefully and each well diluted with 150 µl MeCN/H 2 O/DMSO (8:1:1) and mixed 8 times by the robot in the pipette tips (with aspirating/dispensing). For each well, 40 µl of the quenched reaction solution was pipetted into a new analytical MTP with the same coordinates. To each well was added 160 µl MeCN/H 2 O/DMSO (8:1:1) and mixed 6 times in the tips. The analytical MTP sealed with self-adhesive PP-foil and run over night the UPLC-MS. Results visualised in heat map (see main paper) or 3D plot of the MTP (see Figure S2) in which peak area from HPLC is plotted against the plate positions.
5 Figure S2: 3D plot of the MTP of peak area from HPLC plotted against the plate position A1-H12
6 Validation experiments: Suzuki-Miyaura To three argon flushed 5 ml flat bottomed vials were added 2-(2-(1,1-difluoroethyl)-4-fluorophenyl)- 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (196 mg, 0.68 mmol), degassed 2 % aq TPGS-750-M (2000 µl), degassed co-solvent (PEG or THF, 400 µl) and base (K 3 PO 4, 335 mg, 1.58 mmol or Et 3 N neat 220 µl, 1.58 mmol). The resulting white emulsion/suspension was degassed with argon for 1 min. To this emulsion, catalyst (3 mol%, mmol) was added and the now dark brown reaction mixture was heated to 40 C. After 15 min 2-bromo-3-fluoroaniline (100 mg, 0.53 mmol) was added as liquid. The resulting dark brown emulsion was again degassed with argon and was stirred vigorously at 40 C. Entry Catalyst Base Co-solvent Time (h) UPLC-Conv. (i) RuPhos-Pd-G3 K 3 PO 4 5% THF 5.5 >95% (ii) Pd(dtbpf)Cl 2 K 3 PO 4 5% THF 18 30% (ii) SPhos-Pd-G3 Et 3 N 5% THF 18 30% Table S2: Validation of three Suzuki-Miyaura conditions on 525 µmol scale
7 Figure S3: UPLC-MS plots for three Suzuki-Miyaura conditions on 525 µmol scale
8 Validation experiments: Buchwald-Hartwig To three argon flushed 5 ml flat bottomed vials were added 8-bromo-1,6-naphthyridine (50 mg, 0.24 mmol), tert-butyl carbamate (56 mg, 0.48 mmol), degassed 2 % aq TPGS-750-M (2000 µl), degassed cosolvent (acetone or THF, 400 µl) and base (K 3 PO 4 or Cs 2 CO 3 both 1M 1196 µl, 1.58 mmol). The resulting white emulsion/suspension was degassed with argon for 1 min. To this emulsion, catalyst (10 mol%, mmol) was added and then stirred vigorously at 50 C. Entry Catalyst Base Co-solvent Time (h) UPLC-Conv. (i) tbuxphos-pd-g3 K 3 PO 4 10% acetone 1.5 >95% (ii) tbuxphos-pd-g3 Cs 2 CO 3 10% THF 1 >95% (iii) tbuxphos-pd-g3 K 3 PO 4 10% THF 4 92% Table S3: Validation of three Buchwald-Hartwig conditions on 240 µmol scale
9 Figure S4: UPLC-MS plots for three Buchwald-Hartwig conditions on 240 µmol scale
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