Dimethylamine → 7-[(2,4-Dichloro-5-methoxyphenyl)amino]-3-{4-[(dimethylamino)methyl]phenyl}thieno[3,2-b]pyridine-6-carbonitrile

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A mixture of 7-[(2,4-dichloro-5-methoxyphenyl)amino]-3-(4-formylphenyl)thieno[3,2-b]pyridine-6-carbonitrile (200 mg, 0.44 mmol) and 1.1 mL of a 2 M solution of dimethylamine in tetrahydrofuran (2.20 mmol) in 5 mL of dichloromethane and 1 mL of dimethylformamide is cooled to 0° C. Sodium triacetoxyborohydride (560 mg, 2.64 mmol) is added in portions followed by 3 drops of acetic acid. The resulting mixture is stirred at room temperature for 2.5 hours then quenched by the addition of water. The mixture is partitioned between dichloromethane and saturated aqueous sodium bicarbonate. The organic phase is washed with saturated aqueous sodium chloride, dried over sodium sulfate, filtered and concentrated in vacuo. The residue is purified by flash column chromatography eluting with a gradient of methanol in dichloromethane to provide 147 mg (69%) of 7-[(2,4-dichloro-5-methoxyphenyl)amino]-3-{4-[(dimethylamino)methyl]phenyl}thieno[3,2-b]pyridine-6-carbonitrile as a white solid, mp 201–202° C.; 1 H NMR (DMSO-d6) δ 2.19 (s, 6H), 3.46 (s, 2H), 3.86 (s, 3H), 7.38 (d, J=8 Hz, 2H), 7.42 (s, 1H), 7.78 (s, 1H), 7.89 (d, J=8 Hz, 2H), 8.31 (s, 1H), 8.69 (s, 1H), 9.78 (s, 1H); MS 483.0, 485.0 (M+H)+; HRMS found: 483.08061 (M+H)+.

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