Methyl iodide → 4-amino-N-[3-tert-butyl-2-methoxy-5-(2-methoxypyridin-3-yl)phenyl]-N-methylbenzamide

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Reaction Steps

steps 1 & 2—To a solution of 102 (0.24 g, 0.55 mmol) in THF (5 mL) was added sodium hydride (0.033 g, 0.83 mmol). The mixture was stirred at RT until the evolution of gas subsided, and iodomethane (0.069 mL, 1.1 mmol) was added. The resulting mixture was stirred for 3 h and then quenched with water and the mixture extracted with EtOAc. The solvent was evaporated, and the crude residue was dissolved in EtOAc/hexane (2:1, 10 mL) to which was added 10% Pd/C (0.025 g). A stream of hydrogen gas was bubbled through the solution for 20 min, and the resulting solution was stirred at RT for 3 h. The solution was filtered, the filtrate concentrated, and the crude residue purified by SiO2 chromatography eluting with EtOAc/hexane to afford 0.23 g (97%) of 4-amino-N-[3-tert-butyl-2-methoxy-5-(2-methoxypyridin-3-yl)phenyl]-N-methylbenzamide (140) as a white foam.

Provenance & Evidence