Dimethylformamide → 1-cyclohexylmethyl-3-(3,4-dimethyl-benzoyl)-1H-quinolin-4-one

HRID 226922Notes

Reaction equation

HRID 226922 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[CH3:21])[C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)=[O:6].[H-].[Na+].[CH:24]1([CH2:30]Br)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.CN(C)C=O>CCCCCC.C(OCC)(=O)C>[CH:24]1([CH2:30][N:9]2[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:16](=[O:17])[C:7]([C:5](=[O:6])[C:4]3[CH:18]=[CH:19][C:20]([CH3:21])=[C:2]([CH3:1])[CH:3]=3)=[CH:8]2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 137636Cyclohexane, (bromomethyl)-HCID 577545153-(3,4-Dimethyl-benzoyl)-1H-quinolin-4-one

Product 1

HCID 167310911-cyclohexylmethyl-3-(3,4-dimethyl-benzoyl)-1H-quinolin-4-oneYield 58.2%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The titled compound was prepared following the procedure described in Step 3 of Example 1. 63 mg (0.23 mmol) of 3-(3,4-dimethyl-benzoyl)-1H-quinolin-4-one 3a, 12 mg (0.30 mmol) of 60% sodium hydride and 52 mg (0.30 mmol) of cyclohexylmethyl bromide and 0.9 mL N,N-dimethylformamide were combined at 90° C. for 5 h. Flash chromatography using 10-75% ethyl acetate in hexane yielded 50 mg of the product 4b as white solid: LC-MSD, m/z for C25H27NO2 [M+H]+=374.6; HPLC retention time: 2.8 min; 1H NMR (400 MHz, CDCl3): δ 1.0-1.3 (m, 6H), 1.7-1.85 (m, 4H), 1.9-2.0 (m, 1H), 2.3 (s, 3H), 2.35 (s, 3H), 4.0-4.05 (m, 2H), 7.15-7.2 (m, 1H), 7.4-7.5 (m, 2H), 7.5-7.6 (m, 1H), 7.6 (s, 1H), 7.65-7.75 (m, 1H), 8.05 (s, 1H), 8.45-8.5 (m, 1H).

Workup

  1. customThe titled compound was prepared

Sources & evidence

ORD record
ord-93a60b3adf5542e9a103d4a33d097b65
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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