To a solution of 4-bromo-1-methyl-1H-pyrazole-3-carboxamide (10.0 mg, 0.0490 mmol) in DMF (2 mL, 20 mmol) was added thionyl chloride (0.1 mL, 1 mmol) at 0° C., and the mixture was allowed to warm to rt. The material was extracted with EtOAc, and washed with sat. NaHCO3 (3×). The organic layer was concentrated in vacuo. 3-[(S)-1-(2-Chloro-3-fluoro-6-methoxyphenyl)-ethyl]-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (10.0 mg, 0.0232 mmol), (1,1′bis-(diphenylphosphino)-ferrocene) palladium dichloride (1.79 mg, 0.00245 mmol), K2CO3 (10.0 mg, 0.0724 mmol) and 4:1 dioxane:H2O (1 mL, 10 mmol) were added, and the mixture was heated in a microwave reactor at 100° C. for 30 min. The solution was used directly for HPLC purification, and the fractions containing the pure product were concentrated in vacuo to afford the title compound as a white solid. 1H NMR (400 MHz, CD3OD): δ=1.80 (d, J=7.3 Hz, 3H), 3.72 (br. s., 3H), 4.00 (s, 3H), 5.15 (q, J=6.7 Hz, 1H), 6.90 (dd, J=9.1, 4.3 Hz, 1H), 7.05 (t, J=8.8 Hz, 1H), 7.37 (d, J=1.3 Hz, 1H), 7.82 (s, 1H), 7.98 (s, 1H), 8.31 (d, J=2.0 Hz, 1H). MS (ES+): m/z=410.05/412.06 (100/50) [MH+]. HPLC: tR=4.08 min (polar—5 min, ZQ3).
