Sodium hydride → 3-(3,4-dimethyl-benzoyl)-1-(2-fluoro-benzyl)-2,3-dihydro-1H-quinolin-4-one

HRID 226937Notes

Reaction equation

HRID 226937 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][C:22]=1[CH3:23])[C:7]([C:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1)=[O:8].[F:24][C:25]1[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=1[CH2:27]Br>CN(C)C=O>[CH3:3][C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][C:22]=1[CH3:23])[C:7]([CH:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([CH2:27][C:26]2[CH:29]=[CH:30][CH:31]=[CH:32][C:25]=2[F:24])[CH2:10]1)=[O:8]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 67968alpha-Bromo-o-fluorotolueneHCID 577545153-(3,4-Dimethyl-benzoyl)-1H-quinolin-4-one

Product 1

HCID 668968333-(3,4-dimethyl-benzoyl)-1-(2-fluoro-benzyl)-2,3-dihydro-1H-quinolin-4-oneYield 20.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 3 mL of anhydrous dimethylformamide was suspended 16 mg (0.4 mmol) of sodium hydride (60%), 86 mg (0.31 mmol) of 3-(3,4-dimethyl-benzoyl)-2,3-dihydro-1H-quinolin-4-one 3a was added and the mixture was stirred at rt. After 30 minutes, 75.6 mg (0.40 mmol) of 2-fluorobenzylbromide was added and the reaction was stirred at room temperature for 1 hour. The reaction mixture was quenched by the addition of 10 mL of water. The crude product precipitated out were isolated by filtration and purified by flash chromatography to yield 25 mg of colorless solid 41: LC-MSD, m/z for C25H20FNO2 [M+H]+=386.4, [M+2H]+=387.4; Reverse phase HPLC (gradient acetonitrile 0.1% TFA 20-95% in 4 min) retention time=2.526 min; 1H NMR (400 MHz, CDCl3/HCl): δ 2.2-2.3 (d, 6H), 5.7 (s, 2H), 7.1-7.3 (m, 4H), 7.3-7.4 (m, 1H), 7.4-7.5 (m, 2H),7.54 (s, 1H), 7.6-7.66 (d, 1H), 7.67-7.74 (t, 1H), 8.2 (d, 1H), 8.58 (s, 1H).

Workup

  1. additionwas added
  2. stirringthe reaction was stirred at room temperature for 1 hour
  3. customThe reaction mixture was quenched by the addition of 10 mL of water
  4. customThe crude product precipitated out
  5. customwere isolated by filtration
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-ac7ee47fca1d44daa19fbcd6fd68c2ee
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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