4-Bromo-6-methoxyquinoline → 6-Methoxy-4-vinyl-quinoline

Participants

Reaction Conditions

Reaction Steps

InCl3 (1.1 g, 5 mmol) was dried under HV by heating with a heat gun. After cooling under N2 atmosphere, THF (25 mL) was added and the mixture sonicated until a solution had formed. This solution was cooled to −78° C., and a 1.7M solution of vinyl magnesium chloride (15 mmol) was added dropwise. The mixture was stirred at −78° C. for 15 min, warmed to rt and the resulting solution was added to a refluxing mixture of 4-bromo-6-methoxy-quinoline (1.85 g, 10 mmol) and Pd(dppf)Cl2.CH2Cl2 complex (0.408 g) in THF (25 mL). The mixture was refluxed for 2 h until tlc indicated complete conversion. The mixture was cooled to rt, quenched by addition of a few drops of MeOH and SiO2 (20 g) was added. The volatiles were removed under reduced pressure and the residue was chromatographed over SiO2 (Hex/EA 1:1) to give the desired compound (0.4 g, 21% yield) as a yellowish oil.

Provenance & Evidence