4-Bromo-6-methoxyquinoline-3-carbonitrile synthesis

Yield:872714-52-8 90%

Reaction Conditions:

Stage #1: 4-hydroxy-6-methoxyquinoline-3-carbonitrilewith phosphorus tribromide in N,N-dimethyl-formamide at 0; for 1 h;
Stage #2: with sodium hydroxide in water;N,N-dimethyl-formamide;

Steps:

2.c

c) 4-Bromo-6-(methyloxy)-3-quinolinecarbonitrile; To a suspension of 4-hydroxy-6-(methyloxy)-3-quinolinecarbonitrile (2.19 g, 10.9 mmol, 1 eq) in DMF (20 ml_) at 0 0C was added dropwise PBr (1.1 ml_, 11.6 mmol, 1.06 eq) with efficient stirring. After stirring for 1 h, the suspension was then quenched with NaOH (2.5 N, 200 ml_) and filtered to give the titled compound (2.6 g, 90 % yield) as an off-white solid: LC/MS (ES) m/e 264 (M+H)+.

References:

WO2006/2047,2006,A2 Location in patent:Page/Page column 62-63