Sodium hydride → 3-(3,4-dimethyl-benzoyl)-1-(6-trifluoromethyl-pyridin-2-ylmethyl)-1H-quinolin-4-one

HRID 226969Notes

Reaction equation

HRID 226969 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[CH3:21])[C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)=[O:6].[H-].[Na+].Br[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[N:27]=1>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[CH3:21])[C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:34])([F:33])[F:35])[N:27]=2)[CH:8]=1)=[O:6]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 469414632-(Bromomethyl)-6-(trifluoromethyl)pyridineHCID 577545153-(3,4-Dimethyl-benzoyl)-1H-quinolin-4-one

Product 1

HCID 577546803-(3,4-dimethyl-benzoyl)-1-(6-trifluoromethyl-pyridin-2-ylmethyl)-1H-quinolin-4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 4xx was prepared following the procedure described in Step 3 of Example 1 using 55 mg (0.20 mmol) of 3-(3,4-dimethyl-benzoyl)-1H-quinolin-4-one, 10 mg (0.26 mmol) of 60% sodium hydride and 62 mg (0.26 mmol) of 2-bromomethyl-6-trifluoromethyl-pyridine, and 1.7 mL N,N-dimethylformamide and stirring the reaction mixture for 6 h at rt. The crude product was purified by flash chromatography using 20-75% ethyl acetate in hexane yielded to provide 45 mg of the product as white solid: LC-MSD, m/z for C25H19F3N2O2 [M+H]+: 437.3; Reverse phase HPLC gradient, 20-95% acetonitrile with 0.1% TFA in 4 minutes, retention time=2.8 min; 1H NMR (400 MHz, CDCl3): δ 2.25 (s, 3H), 2.3 (s, 3H), 5.6 (s, 2H), 7.1-7.2 (m, 1H), 7.2-7.3 (m, 1H), 7.3-7.4 (m, 2H), 7.5-7.65 (m, 15 4H), 7.8-7.9 (m, 1H), 8.35 (s, 1H), 8.4-8.5 (m, 1H).

Workup

  1. customThe crude product was purified by flash chromatography
  2. customyielded

Sources & evidence

ORD record
ord-a68cc2f294a0488a804df804d33c00e5
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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