Sodium hydride → 3-Benzoyl-1-[(2-fluorophenyl)methyl]-1,4-dihydroquinolin-4-one

HRID 226943Notes

Reaction equation

HRID 226943 reaction equation
[H-].[Na+].[C:3]([CH:11]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH2:12]1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[F:22][C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[CH2:25]Br>CN(C)C=O>[C:3]([C:11]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([CH2:25][C:24]2[CH:27]=[CH:28][CH:29]=[CH:30][C:23]=2[F:22])[CH:12]=1)(=[O:10])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 67968alpha-Bromo-o-fluorotolueneHCID 668960903-benzoyl-2,3-dihydro-1H-quinolin-4-one

Product 1

HCID 208645473-Benzoyl-1-[(2-fluorophenyl)methyl]-1,4-dihydroquinolin-4-oneYield 37.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 4u was prepared following the procedure outlined in Step 3 of Example 1 using 16 mg (0.4 mmol) of sodium hydride (60%), 75 mg (0.31 mmol) of 3-benzoyl-2,3-dihydro-1H-quinolin-4-one, 3 mL of anhydrous dimethylformamide, and 74 mg (0.40 mmol) of 2-fluorobenzylbromide. The crude product was purified by flash chromatography to yield 42 mg of a colorless solid 4u: LC-MSD, m/z for C23H16FNO2, [M+H]+=358.4, [M+2H]+=359.4; Reverse phase HPLC (gradient acetonitrile 0.1% TFA 20-95% in 4 min) retention time =2.291 min; 1H NMR (400 MHz, CDCl3/HCl): δ 5.42 (s, 2H), 7.00-7.20 (m, 3H), 7.28-7.46 (m, 5H), 7.51 (t, 1H), 7.61 (t, 1H), 7.78-7.86 (m, 2H), 8.32 (d, 1H), 8.46 (m, 1H).

Workup

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

Sources & evidence

ORD record
ord-7db76b3954e74e69b8baa5f27a2c19ff
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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