Potassium Carbonate → HCID 67125601, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3-chloro-N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide (0.204 mmol, 100 mg), potassium carbonate (0.408 mmol, 56.4 mg), 1,1′-bis(diphenylphosphino)ferrocenedichloro palladium(II) (0.020 mmol, 14.77 mg) in THF, was added methylzinc chloride (2.041 mmol, 1020 μl) and stirred overnight at 60° C. The reaction was quenched in water, extracted with ethyl acetate. Organic layer was dried and concentrated under reduced pressure. Crude product was purified with HPLC to give N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-3-methylthieno[2,3-b]pyrazine-6-carboxamide 96l (30 mg, 31%). NMR (400 MHz, DMSO-d6) 1.76 (s, 6H), 2.26 (s, 3H), 2.68 (s, 3H), 7.31 (d, J=8.6 Hz, 1H), 7.62 (m, 2H), 7.76 (d, J=8.6 Hz, 1H), 7.86 (d, J=2.0 Hz, 1H), 7.95 (d, J=7.8 Hz, 1H), 8.06 (s, 1H), 8.50 (s, 1H), 8.78 (s, 1H), 10.36 (s, 1H), 10.45 (s, 1H). (m/z)=471 (M+H)+.

Provenance & Evidence