Sodium borohydride → 3-Fluoro-4-(2-(1-propyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)aniline

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Reaction Steps

To a solution of the nitro compound 132 (4.13 g, 10.36 mmol) in MeOH/THF (100 ml/100 mL) was added NiCl2×6H2O (4.92 g, 20.73 mmol) and NaBH4 (1.54 mg, 41.44 mmol). The reaction mixture was allowed to stir for 1 hr, concentrated to dryness and the resultant solid was dissolved in 2 M HCl. The acidic solution was then made basic with aqueous ammonium hydroxide solution and extracted with EtOAc. The organic extract was dried over anhydrous sodium sulfate, filtered and evaporated The residue was purified by flash chromatography (eluents DCM-MeOH, 98:2, 95:5) to afford title compound 133 (3.31 g, 86% yield) as a pink solid. MS (m/z): 368.1 (M+H).

Provenance & Evidence