Potassium Carbonate → 1-(4-{3-[(1S)-1-(2-Chloro-3-fluoro-6-methoxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-3,5-dimethyl-1H-pyrazol-1-yl)-2-methylpropan-2-ol

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Reaction Steps

A mixture of 5-bromo-3-[(S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridine (20.0 mg, 0.0521 mmol), 1-[3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]-2-methylpropan-2-ol (30.7 mg, 0.104 mmol), Pd(PPh3)4 (3.01 mg, 0.00261 mmol), K2CO3 (21.6 mg, 0.156 mmol) and 4:1 dioxane:water was microwaved at 100° C. for 45 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=1.23 (s, 3H), 1.24 (s, 3H), 1.80 (d, J=7.3 Hz, 3H), 2.07 (s, 3H), 2.17 (s, 3H), 3.65 (br. s., 3H), 4.01 (s, 2H), 5.06-5.15 (m, 1H), 6.89 (dd, J=9.1, 4.0 Hz, 1H), 7.08 (t, J=8.8 Hz, 1H), 7.32 (s, 1H), 7.36 (d, J=1.3 Hz, 1H), 7.99 (d, J=1.8 Hz, 1H). MS (ES+): m/z=471.03/473.01 (100/50) [MH+]. HPLC: tR=3.47 min (polar—5 min, ZQ3).

Provenance & Evidence