To a solution of tert-butyl 5-bromo-3-[(1S)-1-(2-chloro-3-fluoro-6-hydroxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (13.0 mg, 0.0277 mmol) and K2CO3 (12.7 mg, 0.0919 mmol) in DMF (0.8 mL, 10 mmol) was added isopropyl iodide (16.06 mg, 0.09451 mmol), and the mixture was heated to 40° C. for 2 h. The reaction mixture was diluted with EtOAc and washed with water (3×). The organic layer was concentrated in vacuo, and trans-4-[5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]cyclohexanol (12.71 mg, 0.04151 mmol), Pd(PPh3)4 (1.599 mg, 0.001384 mmol), K2CO3 (3 eq) and 4:1 dioxane:H2O (1 mL, 10 mmol) were added. The mixture was heated in a microwave reactor at 95° C. for 20 min. 12 M of HCl in H2O (0.069 mL, 0.83 mmol) was added, and the solution was heated to 45° C. for 1 h. 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=0.68 (br. s., 3H), 1.24 (d, J=5.8 Hz, 3H), 1.45-1.57 (m, 2H), 1.80 (d, J=7.1 Hz, 3H), 1.94-2.11 (m, 6H), 2.19 (s, 3H), 3.68 (tt, J=11.0, 4.2 Hz, 1H), 4.12-4.24 (m, 1H), 4.35-4.51 (m, 1H), 5.01-5.12 (m, 1H), 6.83 (dd, J=8.3, 3.8 Hz, 1H), 7.05 (t, J=8.8 Hz, 1H), 7.33 (dd, J=2.9, 1.6 Hz, 2H), 7.45 (s, 1H), 8.09 (d, J=2.0 Hz, 1H). MS (ES+): m/z=511.34/513.33 (100/50) [MH+]. HPLC: tR=1.33 min (polar—2 min, UPLC-ACQUITY).
