Sodium borohydride → 4-(3-Chloro-4-methoxy-benzylamino)-3-hydroxymethyl-quinoline-6-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To 530 mg (1.0 mmol) of 4-[[(3-chloro-4-methoxyphenyl)methyl]amino]-6-cyano-3-quinolinecarboxylic acid pentafluorophenyl ester was added 15 mL of anhydrous DMF, and the resulting mixture was cooled to 0° C. A solution of 75 mg of NaBH4 in 5 mL of anhydrous DMF was added to the reaction mixture, resulting in a clear red solution with gas evolution. After stirring for 1 hour at 0° C., the reaction was quenched with 2% TFA/MeOH, and the solvent was removed under reduced pressure. The oily residue was purified by flash chromatography (silica gel, 3-5% MeOH/CH2Cl2) to afford 87 mg (25% yield) of the title compound. LC: 2.60′; MH+: 354.

Provenance & Evidence