Methyl iodide → HCID 57545953, compound

Participants

Reaction Steps

tert-Butyl 4-phenyl-4-(((5-(trifluoromethyl)-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)methoxy)methyl)piperidine-1-carboxylate (97 mg, 0.16 mmol) was dissolved in dry tetrahydrofuran (3 mL) and stirred at room temperature for 15 min. The stirred mixture was cooled to −78° C. and treated with a solution of tert-butyllithium (1.7 M in pentane, 190 μL, 0.33 mmol). The reaction was gradually warmed to −20° C. over 1 h, cooled to −78° C. and treated with iodomethane (10 μL, 0.19 mmol). The reaction was warmed to 0° C. over several hours then treated with saturated ammonium chloride. The reaction was diluted with ethyl acetate. The layers were separated and the organic layer washed with brine (2×), dried over sodium sulfate, filtered and concentrated to afford 100 mg (quant.) as a clear oil. LC/MS (HPLC method 1): tR=3.70 min, 634.26(MH)+.

Provenance & Evidence