6-(Bromomethyl)pyridine-2-carbonitrile → 6-[3-(4-Methoxy-3-methyl-benzoyl)-4-oxo-4H-quinolin-1-ylmethyl]-pyridine-2-carbonitrile

HRID 227005Notes

Reaction equation

HRID 227005 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([C:7]([C:9]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][CH:10]=2)=[O:8])=[CH:5][C:4]=1[CH3:22].Br[CH2:24][C:25]1[N:30]=[C:29]([C:31]#[N:32])[CH:28]=[CH:27][CH:26]=1>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([C:7]([C:9]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:24][C:25]3[N:30]=[C:29]([C:31]#[N:32])[CH:28]=[CH:27][CH:26]=3)[CH:10]=2)=[O:8])=[CH:5][C:4]=1[CH3:22]

Participants

4

Reactant 2

HCID 272816606-(Bromomethyl)pyridine-2-carbonitrileHCID 577547583-(4-Methoxy-3-methyl-benzoyl)-1H-quinolin-4-one

Product 1

HCID 577546306-[3-(4-Methoxy-3-methyl-benzoyl)-4-oxo-4H-quinolin-1-ylmethyl]-pyridine-2-carbonitrileYield 41.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Experimental conditions analogous to those described for Step 3 of Example 1 were used with 100 mg (0.341 mmol) of 3-(4-Methoxy-3-methyl-benzoyl)-1H-quinolin-4-one, 80.6 mg (0.409 mmol) of 6-bromomethyl-pyridine-2-carbonitrile, 16.4 mg (0.409 mmol, 60% dispersion in oil), and 3.5 mL of N,N-dimethylformamide. The crude product was purified by flash column chromatography using a gradient of 20-100% ethyl acetate in hexane to yield 58 mg of 6-[3-(4-Methoxy-3-methyl-benzoyl)-4-oxo-4H-quinolin-1-ylmethyl]-pyridine-2-carbonitrile. LC-MSD, m/z for C25H19N3O3 [M+H]: 410.14 LC retention time on HPLC, C18 column gradient 20-95% acetonitrile with 0.1% TFA in 4 minutes: 2.3 min.

Workup

  1. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-f5310cda80b449de9570239bb5c849bf
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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