Cesium carbonate → HCID 178480803, compound

Participants

Reaction Conditions

Reaction Steps

To a solution tert-butyl(trans-3-{[2-chloro-5-(pyridin-2-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy}cyclobutyl)carbamate (439 mg, 0.804 mmol) in 1,4-dioxane (8 mL) in a microwave vial was added 1-methyl-1H-pyrazol-4-amine (78.1 mg, 0.804 mmol) followed by cesium carbonate (524 mg, 1.61 mmol), tris(dibenzylideneacetone)dipalladium(0) (73.3 mg, 0.08 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (46.3 mg, 0.08 mmol) and the resulting mixture heated in the microwave to 140° C. for 45 minutes. The reaction was cooled to rt, filtered through a celite plug and stripped to a dark oil that was purified via flash chromatography (20%-100% EtOAc I heptane, then 10% methanol in EtOAc) to afford the title compound as a tan solid (365 mg, 75% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.03-9.14 (m, 1H) 8.44-8.55 (m, 1H) 8.00-8.09 (m, 1H) 7.81-7.92 (m, 1H) 7.74-7.80 (m, 1H) 7.57-7.64 (m, 1H) 7.42-7.48 (m, 1H) 7.21-7.32 (m, 1H) 7.11-7.20 (m, 1H) 5.45-5.53 (m, 2H) 5.35-5.42 (m, 1H) 4.02-4.15 (m, 1H) 3.74 (s, 3H) 3.45-3.56 (m, 2H) 2.28-2.39 (m, 4H) 1.31 (s, 9H) 0.74-0.81 (m, 2H) −0.20 (s, 9H). m/z (APCI+) for C30H42N8O4Si 607.2 (M+H)+.

Provenance & Evidence