A mixture of tert-butyl 5-bromo-3-{(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl]ethyl}-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (45.0 mg, 0.0866 mmol), 1-{[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (41.85 mg, 0.1299 mmol), Pd(PPh3)4 (5.002 mg, 0.004329 mmol), K2CO3 (35.90 mg, 0.2597 mmol) and 4:1 dioxane:H2O (2 mL, 20 mmol) was heated to 95° C. for 2 h. The solution was cooled to rt, and 12 M of HCl in H2O (0.072 mL, 0.87 mmol) was added. The material was concentrated in vacuo, and extracted with DCM and sat. NaHCO3. The organic layer was dry-loaded onto silica gel and purified via column chromatography, eluting with 2-4% (7N NH3 in MeOH)/DCM. The fractions containing the pure product were concentrated in vacuo, redissolved in MeOH, and 2.0 M of HCl in Et2O (0.4329 mL, 0.8658 mmol) was added at rt. The solution was concentrated in vacuo to afford the title compound as an HCl salt. 1H NMR (400 MHz, CD3OD): δ=1.85 (d, J=7.3 Hz, 3H), 2.27 (s, 3H), 3.50-3.63 (m, 2H), 4.00-4.09 (m, 1H), 4.15 (dd, J=14.1, 7.6 Hz, 1H), 4.25 (dd, J=14.3, 4.4 Hz, 1H), 5.12 (q, J=7.1 Hz, 1H), 6.44 (br. s., 1H), 7.14 (dd, J=8.7, 4.4 Hz, 1H), 7.20 (t, J=8.7 Hz, 1H), 7.35-7.45 (m, 2H), 7.52 (s, 1H), 8.16 (d, J=2.0 Hz, 1H). MS (ES+): m/z=494.99/496.98 (100/50) [MH+]. HPLC: tR=1.29 min (polar—3 min, UPLC-ACQUITY).
