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

HRID 1368922Notes

Reaction equation

FC1C([O:8][C:9]([C:11]2[CH:12]=[N:13][C:14]3[C:19]([C:20]=2[NH:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([Cl:31])[CH:24]=2)=[CH:18][C:17]([C:32]#[N:33])=[CH:16][CH:15]=3)=O)=C(F)C(F)=C(F)C=1F.[BH4-].[Na+]>CN(C=O)C>[Cl:31][C:25]1[CH:24]=[C:23]([CH2:22][NH:21][C:20]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:32]#[N:33])[CH:18]=3)[N:13]=[CH:12][C:11]=2[CH2:9][OH:8])[CH:28]=[CH:27][C:26]=1[O:29][CH3:30]

Participants

Conditions

Temperature: 0 °C

Procedure

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 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.

Workup

customresulting in a clear red solution with gas evolution
customthe reaction was quenched with 2% TFA/MeOH
customthe solvent was removed under reduced pressure
customThe oily residue was purified by flash chromatography (silica gel, 3-5% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-dc0bbdc2304a4495b6c68dbcc521deb0
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06576644B2

Reaction notes

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