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

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Reaction Steps

To a solution of N-(3-amino-4-methylphenyl)-3-(2-cyanopropan-2-yl)benzamide hydrochloride 6 (230 mg, 0.697 mmol) in toluene (4 mL) was added trimethylaluminum (1.393 mL, 2.79 mmol). After stirring for 15 min, ethyl 7-bromothieno[3,2-b]pyrazine-6-carboxylate 41 (200 mg, 0.697 mmol) in toluene (4 mL) was added and stirred overnight at 60° C. Quenched with 0.5N NaOH solution and extracted with EtOAc. Organic layer was washed with brine, dried and evaporated. Purification by chromatography (0-10% EtOAc in CH2Cl2) gave the title compound 7-bromo-N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide 42 (268 mg, 72.0%). NMR (400 MHz, CDCl3) 1.80 (s, 6H), 2.49 (s, 3H), 7.31 (d, J=8.2 Hz, 1H), 7.54 (t, J=7.8 Hz, 1H), 7.74 (m, 1H), 7.80 (d, J=7.8 Hz, 2H), 7.95 (s, 1H), 8.00 (s, 1H), 8.36 (d, J=2.3 Hz, 1H), 8.71 (d, J=2.3 Hz, 1H), 8.84 (d, J=2.3 Hz, 1H), 9.10 (s, 1H). (m/z)=534 and 536 (M+H)+.

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