Sodium hydride → 1-(2-Fluoro-benzyl)-3-(3-methyl-benzoyl)-1H-quinolin-4-one

HRID 226946Notes

Reaction equation

HRID 226946 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][CH:22]=1)[C:7]([CH:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][CH2:10]1)=[O:8].[F:23][C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH2:26]Br>CN(C)C=O>[F:23][C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH2:26][N:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18](=[O:19])[C:9]([C:7](=[O:8])[C:6]2[CH:20]=[CH:21][CH:22]=[C:4]([CH3:3])[CH:5]=2)=[CH:10]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 67968alpha-Bromo-o-fluorotolueneHCID 670719523-(3-methyl-benzoyl)-2,3-dihydro-1H-quinolin-4-one

Product 1

HCID 167308541-(2-Fluoro-benzyl)-3-(3-methyl-benzoyl)-1H-quinolin-4-oneYield 45.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 4x was prepared following the procedure outlined in Step 3 of Example 1 using 26 mg (0.65 mmol) of sodium hydride (60%), 132 mg (0.50 mmol) of 3-(3-methyl-benzoyl)-2,3-dihydro-1H-quinolin-4-one, 3 mL of anhydrous dimethylformamide, and 123 mg (0.65 mmol) of 2-fluorobenzylbromide. The crude product was purified by flash chromatography to yield 85 mg of a colorless solid 4x: LC-MSD, m/z for C24H18FNO2, [M+H]+=372.4, [M+2H]+=373.4; Reverse phase HPLC (gradient acetonitrile 0.1% TFA 20-95% in 4 min) retention time=2.687 min; 1H NMR (400 MHz, CDCl3/HCl): δ 2.40 (s, 3H), 5.42 (s, 2H), 7.02-7.18 (m, 3H), 7.28-7.36 (m, 3H), 7.36-7.42 (m, 2H), 7.58-7.66 (m, 3H), 8.31 (s, 1H), 8.43-8.47 (m, 1H).

Workup

  1. customCompound 4x was prepared
  2. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-74d43efcbe7647d9844834ffb73d2259
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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