Methyl iodide → HCID 70663708, compound

Participants

Reaction Steps

To a stirring solution of tert-butyl 4-(4-fluoro-2-methylphenyl)pyridin-3-ylcarbamate (230 mg, 0.76 mmol) in THF (5 mL) under argon was added NaH (23.9 mg, 1 mmol). After 15 min iodomethane (62 μL, 1 mmol) was added and the reaction mixture was stirred for 1 h. The reaction mixture was poured into saturated aqueous NH4Cl solution and extracted three times with EtOAc. The combined organic phases were washed with brine and dried over MgSO4. Filtration followed by removal of volatiles under reduced pressure gave the N-methylated product [4-(4-fluoro-2-methyl-phenyl)-pyridin-3-yl]-methyl-carbamic acid tert-butyl ester as a light brown oil. This oil was treated with 4M HCl in dioxane for 1 h. Removal of volatiles gave an oily solid which was suspended in CH2Cl2 and washed with 1M aqueous K2CO3 solution. The aqueous phase was extracted twice more with CH2Cl2 and the combined organic phases were dried over MgSO4. Filtration followed by removal of volatiles gave the desired product (113 mg, 69%) which was pure enough for the next step without further purification.

Provenance & Evidence