2,4-Dimethylaniline → HCID 131735559, 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 mol), 2,4-dimethylaniline (85.1 mg, 526 mol), BINAP (14.6 mg, 23.4 mol), palladium (II) acetate (26.3 mg, 117 mol) and sodium tert-butoxide (112 mg, 1.17 mmol) in DMF (1 mL) and toluene (500 μL) was heated in a microwave at 140° C. for 20 min. The reaction mixture was diluted with water then extracted into ethyl acetate (3×). The combined organic extracts were washed with brine then dried over magnesium sulfate. Purification by chromatography (silica, 20-60% ethyl acetate in hexanes) gave N-tert-butyl-2-(2,4-dimethylphenylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (82 mg, 175 mol, 37.5%) as a brown gum. (EI/CI) m/z: 468.4 [M+H].

Provenance & Evidence