Sulfuric Acid → 4-Amino-2-iodo-thieno[3,2-c]pyridine-7-carboxylic acid amide

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Reaction Steps

To 2-iodo-4-(4-methoxy-benzylamino)-thieno[3,2-c]pyridine-7-carbonitrile 27 (3.88 g, 9.21 mmol) was added conc. H2SO4 (9.75 mL). The reaction was stirred for 1 h at room temperature, then quenched by the addition of ice (20 g). The filtered precipitate was washed with H2O, then suspended in 30% MeOH—CH2Cl2 (30 mL). Triethylamine was added dropwise until the solids dissolved. The solution was purified by silica gel column chromatography (eluent: 10 to 20% MeOH in CH2Cl2 with 1% NH4OH additive) to yield 2.6 g of 28. 1H NMR (400 MHz, d6-DMSO) δ 8.46 (s, 1H), 7.94 (m, 2H), 7.31 (bs, 1H), 7.18 (s, 2H).

Provenance & Evidence