N-methyl-2-pyrrolidone → 2-Amino-6-methoxymethyl-nicotinic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-amino-6-chloro-nicotinic acid methyl ester (1.4 g) described in Manufacturing Example 11-2, tributyl-methoxymethyl-tin (3.1 g) described in Manufacturing Example 11-3-1, tetrakis(triphenylphosphine)palladium(0) (440 mg), and NMP (20 mL) was stirred for 3.5 hours at 130° C. The reaction solution was allowed to cool, an aqueous potassium fluoride solution and ethyl acetate were added thereto under ice cooling, after which the reaction mixture was filtered through Celite. The organic layer was washed with saturated brine, after which the solvent was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1) to obtain the titled compound (0.93 g).

Provenance & Evidence