Ethyl Acetate → 3-(3,4-Dimethyl-benzoyl)-1-(2-fluoro-benzyl)-6-trifluoromethyl-1H-quinolin-4-one

HRID 226926Notes

Reaction equation

HRID 226926 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[CH3:25])[C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:18]([F:21])([F:20])[F:19])[CH:14]=2)[NH:9][CH:8]=1)=[O:6].[H-].[Na+].[F:28][C:29]1[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=1[CH2:31]Br.C(OCC)(=O)C>CN(C)C=O.CCCCCC>[CH3:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[CH3:25])[C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:18]([F:21])([F:19])[F:20])[CH:14]=2)[N:9]([CH2:31][C:30]2[CH:33]=[CH:34][CH:35]=[CH:36][C:29]=2[F:28])[CH:8]=1)=[O:6]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 67968alpha-Bromo-o-fluorotolueneHCID 577545723-(3,4-dimethyl-benzoyl)-6-trifluoromethyl-1H-quinolin-4-one

Product 1

HCID 167306153-(3,4-Dimethyl-benzoyl)-1-(2-fluoro-benzyl)-6-trifluoromethyl-1H-quinolin-4-oneYield 79.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

Compound 4f was prepared following the procedure described in Step 3 of Example 1. Briefly described here, 55 mg (0.16 mmol) of 3-(3,4-dimethyl-benzoyl)-6-trifluoromethyl-1H-quinolin-4-one 3b, 8 mg (0.21 mmol) of 60% sodium hydride and 40 mg (0.21 mmol) of 2-fluorobenzyl bromide were combined in 0.5 mL N,N-dimethylformamide at rt for 16 h. Flash chromatography of the crude product using 10-80% ethyl acetate in hexane yielded 58 mg of the product 4f as white solid: LC-MSD, m/z for C26H19F4NO2 [M+H]+=454.5, HPLC retention time: 2.9 min: 1H NMR (400 MHz, CDCl3): δ 2.3 (s, 3H), 2.35 (s, 3H), 5.5 (s, 2H), 7.05-7.2 (m, 4H), 7.3-7.4 (m, 1H), 7.5-7.6 (m, 2H), 7.65 (s, 1H), 7.8-7.85 (m, 1H), 8.3 (s, 1H), 8.75-8.8 (m, 1H).

Workup

  1. customCompound 4f was prepared

Sources & evidence

ORD record
ord-96ed4000cc564f2a98bca837964d7c4c
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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