Dimethylformamide → HCID 90041067, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-bromo-N-isopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (150 mg, 363 μmol), 5-methylpyridin-2-amine (58.9 mg, 544 μmol), BINAP (11.3 mg, 18.1 μmol), palladium (II) acetate (20.4 mg, 90.7 μmol) and sodium tert-butoxide (87.2 mg, 907 μmol) was added DMF (780 μL) and toluene (390 μL) was heated in a microwave at 140° C. for 20 min. The mixture was cooled then diluted with water and ethyl acetate. The mixture was extracted with ethyl acetate (3×) then the organic extracts were combined and washed with brine, dried over magnesium sulfate and purified by chromatography (silica, 30-70% ethyl acetate in hexanes) to give N-isopropyl-2-(5-methylpyridin-2-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (90 mg, 204 μmol, 56%) as an off-white solid. MS (EI/CI) m/z: 441.3 [M+H].

Provenance & Evidence