Cesium carbonate → HCID 90040984, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-bromo-N-tert-butyl-3-chloro-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (125 mg, 271 μmol), 3-methylisothiazol-5-amine hydrochloride (61.2 mg, 406 μmol), Pd2(dba)3 (24.8 mg, 27.1 μmol), xantphos (47.0 mg, 81.2 μmol) and cesium carbonate (265 mg, 812 μmol) in dioxane (1.5 mL) was heated in a microwave at 150° C. for 20 min. Pd2(dba)3 (24.8 mg, 27.1 μmol) and xantphos (47.0 mg, 81.2 μmol) were added and continued to heat in a microwave at 150° C. for 30 min. The mixture was cooled then filtered through a pad of celite. The filtrate was concentrated in vacuo then purified by chromatography (silica, 10-50% ethyl acetate in hexanes) to give N-tert-butyl-3-chloro-2-(3-methylisothiazol-5-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (40 mg, 48.5 μmol, 17.9%) as brown gum. (EI/CI) m/z: 495.1 [M+H].

Provenance & Evidence