Dichloromethane → HCID 54674514, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-bromo-5-chloro-1-methyl-1H-pyrazole (10.2 mg, 0.0522 mmol), 3-[(S)-1-(2-chloro-3-fluoro-6-methoxy-phenyl)-ethyl]-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (15 mg, 0.035 mmol), potassium carbonate (14.4 mg, 0.104 mmol), and 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) dichloride, dichloromethane (1.42 mg, 0.00174 mmol) in previously degassed 4:1 dioxane:water (1.0 mL) was evacuated and charged with N2 (2×) and heated under microwave conditions [Biotage, 100° C., 30 min, high absorption]. The reaction was then charged with an additional 4-bromo-5-chloro-1-methyl-1H-pyrazole (10.2 mg, 0.0522 mmol) and charged with Pd(PPh3)4 (2.01 mg, 0.00174 mmol) and evacuated and charged with N2 (2×) and heated under microwave conditions [Biotage, 100° C., 30 min, high absorption]. A small water layer was removed from MW vial and the crude sample was purified by HPLC resulting the title compound as an off-white solid. 1H NMR (400 MHz, CD3OD): δ=1.80 (d, J=7.1 Hz, 3H), 3.64 (br. s., 3H), 3.88 (s, 3H), 5.11 (d, J=6.8 Hz, 1H), 6.89 (dd, J=4.0, 8.6 Hz, 1H), 7.08 (dd, J=8.8, 8.8 Hz, 1H), 7.35 (s, 1H), 7.65-7.73 (m, 2H), 8.22-8.29 (m, 1H). MS (ES+): m/z 419.05, 421.03 (76/24) [MH+]. HPLC: tR=3.70 min (polar—5 min, ZQ3).

Provenance & Evidence