Methyl iodide → (5-Bromo-6-nitro-pyridin-2-yl)-methyl-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of (5-bromo-6-nitro-pyridin-2-yl)-carbamic acid tert-butyl ester (11) (800 mg, 2.52 mmol) in dry DMF (15 mL), NaH (60% dispersion in mineral oil, 191 mg, 4.53 mmol) was added at 0° C. The resulting mixture was stirred for 30 minutes at 0° C. and methyl iodide (0.23 mL, 3.68 mmol) was then added. After stirring the reaction mixture for 30 minutes at 10° C., saturated aqueous NH4Cl (15 mL) was added. The reaction mixture was extracted with ethyl acetate (3×30 mL). The combined extracts were washed with water, brine, dried over MgSO4 (anhydrous) and concentrated under reduced pressure. The crude product was purified by Biotage using 10% ethyl acetate in hexane to afford (5-bromo-6-nitro-pyridin-2-yl)-methyl-carbamic acid tert-butyl ester 12 (789 mg).

Provenance & Evidence