Dimethylformamide → HCID 131735546, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 5-methylpyridin-2-amine (38.0 mg, 351 μmol), 2-bromo-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (100 mg, 234 μmol) (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (7.28 mg, 11.7 μmol), palladium(II) acetate (13.1 mg, 58.5 μmol) and sodium tert-butoxide (56.2 mg, 585 μmol) was added DMF (1 mL) and toluene (500 μL) and the mixture heated in a microwave at 140° C. for 20 min. The dark mixture generated was poured into water and extracted with ethyl acetate. The organic layers were combined, washed with brine, dried (magnesium sulfate), filtered and purified by chromatography (silica, 30-70% ethyl acetate in hexanes) to give N-tert-butyl-2-(5-methylpyridin-2-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (62 mg, 136 μmol, 58%) as an off white solid. MS (EI/CI) m/z: 455.3 [M+H].

Provenance & Evidence