Potassium Carbonate → HCID 71279632, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-chloro-N-methylacetamide (80 mg, 744 μmol) in DMF (28.0 mL) under Ar, potassium carbonate (280 mg, 2.03 mmol) was added at 25° C. After 1 h, N-tert-butyl-2-(5-(difluoromethoxy)-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (70 mg, 132 μmol) in DMF (7.00 mL) was added and the reaction was stirred at 70° C. After 6 h, the reaction was cooled to 25° C. and quenched with water (350 mL). The product was extracted with ethyl acetate (2×250 mL). The organic layer was dried over sodium sulfate, filtered through Celite, and the solvent removed in vacuo to give a beige solid. The solid was triturated in hexanes (20 mL), filtered and dried in vacuo (200 mTorr, 25° C.) to give N-tert-butyl-2-(5-(difluoromethoxy)-1-(2-(methylamino)-2-oxoethyl)-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (62.2 mg, 103 μmol, 78%) as a light brown solid. MS (M)'=602; 1H NMR (DMSO-d6) δ: 9.10 (s, 1H), 8.60 (s, 1H), 8.22 (m, 2H), 7.88 (s, 1H), 7.82 (d, J=9.0 Hz, 1H), 7.41 (dd, J=2.3, 9.0 Hz, 1H), 7.21 (t, J=74.5 Hz, 1H), 5.73 (s, 2H), 5.27 (s 2H), 3.58 (t, J=8.0 Hz, 2H), 2.65 (d, J=4.5 Hz, 3H), 1.51 (s, 9H), 0.86 (t, J=7.8 Hz, 2H), −0.08 (s, 9H).

Provenance & Evidence