Binap, (A+-)- → HCID 73295442, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-bromo-N-tert-butyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (80 mg, 269 μmol), 2-amino-N,N-dimethylbenzamide hydrochloride (81.0 mg, 404 μmol), BINAP (8.38 mg, 13.5 μmol), palladium (II) acetate (15.1 mg, 67.3 μmol) and sodium tert-butoxide (77.6 mg, 808 μmol, Eq: 3) 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 (15-45% dichloromethane/[10% dichloromethane/methanol/0.5% ammonium hydroxide]) gave N-tert-butyl-2(2(dimethylcarbamoyl)phenylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (16 mg, 42.1 μmol, 16%) as an off-white solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.25 (s, 1H), 8.77 (s, 1H), 8.06 (s, 1H), 7.96 (d, J=3.0, 1 H), 7.91 (d, J=7.9, 1 H), 7.78 (s, 1H), 7.38 (t, J=7.7, 1 H), 7.30 (d, J=7.5, 1 H), 7.11 (t, J=7.5, 1 H), 2.88 (s, 3H), 2.80 (s, 3H), 1.27 (s, 9H); MS (EI/CI) m/z: 381.2 [M+H].

Provenance & Evidence