Methanol → 3-Pyridin-2-ylethynyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazol-6-ylamine

Participants

Reaction Steps

A mixture of 6-Nitro-3-pyridin-2-ylethynyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole (2 mmol), SnCl2 (1.37 g, 6.0 mmol), water (0.5 mL), and MeOH (10 mL), were stirred in a 60 deg C oil bath for 30 min at which time HPLC indicated complete reduction. The resulting mixture was stripped of methanol, suspended in EtOAc (50 mL) and diluted with 1M NaOH (18 mL). The resulting emulsion was gently extracted EtOAc (10×25 ml). The combined organics were extracted with 1M Na2CO3, brine, dried over MgSO4, concentrated and filtered through a pad of silica eluted with EtOAc. The yield of crude product for two steps was 701 mg, 96% mass recovery. ESIMS (M+H+): 365.1.

Provenance & Evidence