Water → N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-7-methylthieno[2,3-b]pyrazine-6-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 7-bromo-N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide 42 (20 mg, 0.037 mmol) and 1,1′-bis(diphenylphosphino) ferrocene palladium (ii) chloride, complex with dichloromethane (1.513 mg, 1.871 μmol) in THF (1 mL) was added methylzinc chloride (0.037 mL, 0.075 mmol). The reaction was stirred at 60° C. for 2 h. Water was added and the resulting precipitate was collected. Purification by chromatography (20% EtOAc in CH2Cl2) gave the title compound N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-7-methylthieno[2,3-b]pyrazine-6-carboxamide 43a (4 mg, 22%) NMR (400 MHz, CDCl3) 2.38 (s, 3H), 2.89 (s, 3H), 7.29 (m, 1H), 7.55 (m, 1H), 7.70-7.83 (m, 4H), 7.91 (s, 1H), 7.99 (m, 1H), 8.26 (d, J=1.9 Hz, 1H), 8.64 (d, J=2.3 Hz, 1H), 8.76 (d, J=2.3 Hz, 1H). (m/z)=470 (M+H)+.

Provenance & Evidence