4-(Dimethylamino)Benzaldehyde → 4-(6-Bromo-7-(4-(methylsulfonyl)piperazin-1-yl)-3h-imidazo[4,5-b]pyridin-2-yl)-n,n-dimethylaniline

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Reaction Steps

This was prepared using the same procedure as for 4-(6-bromo-2-(4-(dimethylamino)phenyl)-3H-imidazo[4,5-b]pyridin-7-yl)-N-phenylpiperazine-1-carboxamide, but here using 5-bromo-4-(4-(methylsulfonyl)piperazin-1-yl)-3-nitropyridin-2-amine (100 mg, 0.26 mmol), DMF (1.6 mL), ethanol (0.2 mL), 1M Na2S2O4 (4 eq, 1.05 mmol, 1.05 mL) and 4-(N,N-dimethylamino)benzaldehyde (1.1 eq, 0.29 mmol, 43 mg). After 6 h, filtration of the precipitate and washing with cold ethanol (1 mL) and cold water (1 mL) gave the product (49 mg, 39%) as a pale yellow solid; 1H-NMR (500 MHz, DMSO-d6) 2.97 (s, 3H, SO2CH3), 3.01 (s, 6H, N(CH3)2), 3.34-3.38 (m, 4H, piperazine N(CH2)2), 3.70-3.73 (m, 4H, piperazine N(CH2)2), 6.83 (d, J=9.0 Hz, 2H, N,N-dimethylaminophenyl) 8.05 (d, J=8.9 Hz, 2H, N,N-dimethylaminophenyl), 8.21 (s, 1H, imidazo[4,5-b]pyridine H-5), 13.21 (br s, 1H, imidazo[4,5-b]pyridine NH);

Provenance & Evidence