Phenethyl bromide → HCID 16730931, compound

HRID 226949Notes

Reaction equation

HRID 226949 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].[CH2:24](Br)[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C)C=O>[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)[N:11]([CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:10]=1)=[O:8]

Participants

5

Reactant 3

HCID 7666Phenethyl bromideHCID 24758Sodium hydrideHCID 577545153-(3,4-Dimethyl-benzoyl)-1H-quinolin-4-one

Product 1

HCID 16730931HCID 16730931, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 4aa was prepared following the procedure outlined in Step 3 of Example 1 using 26 mg (0.65 mmol) of sodium hydride (60%), 138.6 mg (0.50 mmol) of 3-(3,4-dimethyl-benzoyl)-2,3-dihydro-1H-quinolin-4-one 3a, 3 mL of anhydrous dimethylformamide, and 120.3 mg (0.65 mmol) of phenethylbromide. The crude product was purified by flash chromatograph to yield 44 mg of a colorless solid 4aa: LC-MSD, m/z for C26H23NO2, [M+H]+=382.5, [M+2H]+=383.5; Reverse phase HPLC (gradient acetonitrile 0.1% TFA 20-95% in 4 min) retention time=2.551 min; 1H NMR (400 MHz, CDCl3/HCl): δ 2.30 (d, 6H), 3.20 (t, 2H), 4.40 (t, 3H), 7.08 (d, 2H), 7.13 (d, 1H), 7.20-7.32 (m, 3H), 7.38-7.47 (m, 2H), 7.53-7.58 (d, 2H), 7.73 (t, 1H), 7.80 (s, 1H), 8.48 (d, 1H).

Workup

  1. customThe crude product was purified by flash chromatograph

Sources & evidence

ORD record
ord-300554d13b064852a95fd7eeffee8965
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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