Dimethylformamide → HCID 131735547, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-bromo-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (200 mg, 468 μmol), 1-methyl-1H-pyrazol-3-amine (68.2 mg, 702 μmol), BINAP (14.6 mg, 23.4 μmol), palladium (II) acetate (26.3 mg, 117 μmol) and sodium tert-butoxide (112 mg, 1.17 mmol) was added DMF (1.01 mL) and toluene (503 μL) was heated in a microwave at 140° C. for 20 min. The reaction mixture was cooled then diluted with water and extracted into ethyl acetate. The organic layers were combined and washed with brine and then dried over magnesium sulfate. Purification by chromatography (silica, 20-100% ethyl acetate in hexanes) gave N-tert-butyl-2-(1-methyl-1H-pyrazol-3-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (140 mg, 316 μmol, 67%) as a yellow solid. MS (EI/CI) m/z: 444.3.

Provenance & Evidence