Ammonium Chloride → 2-Fluoro-N1-(2-(1-methyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yl)benzene-1,4-diamine

Participants

Reaction Steps

To a stirred suspension of nitro compound 338 (370 mg, 1.00 mmol) in a mixture of MeOH (20 mL) and water (10 mL) were added iron powder (280 mg, 5.01 mmol) and NH4Cl (107 mg, 2.00 mmol). The reaction mixture heated to reflux for 2 hrs, cooled down to room temperature, filtered through Celite, and rinsed with methanol. The filtrate was concentrated, diluted a bit with methanol, precipitated with AcOEt/hexanes to afford title compound 339 (463 mg, quantitative yield, ammonium salt) as a yellow solid. MS (m/z): 340.0 (M+H)+.

Provenance & Evidence