Sodium Dithionite → 6-Bromo-2-(4-methoxyphenyl)-7-(4-(1-(pyridin-4-yl)ethyl)piperazin-1-yl)-3h-imidazo[4,5-b]pyridine

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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-3-nitro-4-(4-(1-(pyridin-4-yl)ethyl)piperazin-1-yl)pyridin-2-amine (30 mg, 0.074 mmol), DMF (1 mL), 1M Na2S2O4 (3 eq, 0.22 mmol, 0.22 mL) and 4-methoxybenzene carboxaldehyde (1.05 eq, 0.077 mmol, 0.0096 mL). After 16 h, filtration of the precipitate and washing with ethanol (1 mL) and cold water (1 mL) gave the product (15 mg, 42%) as a pale yellow solid; 1H-NMR (500 MHz, DMSO-d6) 1.37 (d, J=6.7 Hz, 3H, CHCH3), 2.56-2.65 (2 m, 4H, piperazine N(CH2)2), 3.58 (q, J=6.9 Hz, 1H, CHCH3), 3.66 (br s, 4H, piperazine N(CH2)2), 3.85 (s, 3H, OCH3), 7.11 (d, J=8.8 Hz, 2H, methoxyphenyl), 7.40 (d, J=5.4 Hz, 2H, pyridine H-3 & H-5), 8.14 (d, J=8.5 Hz, 2H, methoxyphenyl), 8.20 (s, 1H, imidazo[4,5-b]pyridine H-5), 8.55 (d, J=5.4 Hz, 2H, pyridine H-2 & H-6), 13.40 (br s, 1H, imidazo[4,5-b]pyridine NH);

Provenance & Evidence