1-(Bromomethyl)-3-(trifluoromethyl)benzene → 3-(2,3-Dihydro-benzo[1,4]dioxine-6-carbonyl)-1-(3-trifluoromethyl-benzyl)-1H-quinolin-4-one

HRID 227143Notes

Reaction equation

HRID 227143 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([C:13]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[NH:15][CH:14]=3)=[O:12])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.Br[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=1>>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([C:13]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[N:15]([CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:33])([F:34])[F:35])[CH:27]=4)[CH:14]=3)=[O:12])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 1230611-(Bromomethyl)-3-(trifluoromethyl)benzeneHCID 577545433-(2,3-Dihydro-benzo[1,4]dioxine-6-carbonyl)-1H-quinolin-4-one

Product 1

HCID 577546933-(2,3-Dihydro-benzo[1,4]dioxine-6-carbonyl)-1-(3-trifluoromethyl-benzyl)-1H-quinolin-4-oneYield 15.2%

Procedure

Experimental conditions analogous to those described for Step 3 of Example 1, from 3-(2,3-Dihydro-benzo[1,4]dioxine-6-carbonyl)-1H-quinolin-4-one 70.7 mg (0.296 mmol) and 71.1 mg (0.296 mmol) of 1-Bromomethyl-3-trifluoromethyl-benzene, to give 21 mg of desired compound. LCMS (M+H)+: 466.

Sources & evidence

ORD record
ord-bac32053f8194129af9b6aee643b9ef8
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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