Bromide ion → Formate

Participants

Reaction Steps

4-{(2S,4R)-1-Acetyl-4-[(4-chlorophenyl)amino]-2-methyl-1,2,3,4-tetrahydro-6-quinolinyl}benzoic acid (for a preparation see Intermediate 18) (150 mg, 0.345 mmol) was dissolved in DMF (3 mL) and K2CO3 (47.7 mg, 0.345 mmol) then 3-bromo-N,N,N-trimethyl-1-propanaminium, bromide (90 mg, 0.345 mmol) were added. The resulting mixture was stirred at room temperature overnight, whereupon the reaction mixture was concentrated in vacuo and purified by MDAP (formate) to give 3-{[(4-{(2S,4R)-1-acetyl-4-[(4-chlorophenyl)amino]-2-methyl-1,2,3,4-tetrahydro-6-quinolinyl}phenyl)carbonyl]oxy}-N,N,N-trimethyl-1-propanaminium, formate (41 mg, 0.064 mmol, 19% yield) as a yellow oil. LCMS (Formate, 2 min), Rt=0.86 min, MH+=534.

Provenance & Evidence