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

HRID 227140Notes

Reaction equation

HRID 227140 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])[N: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:34])([F:33])[F:35])[N:27]=4)[CH:14]=3)=[O:12])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 469414632-(Bromomethyl)-6-(trifluoromethyl)pyridineHCID 577545433-(2,3-Dihydro-benzo[1,4]dioxine-6-carbonyl)-1H-quinolin-4-one

Product 1

HCID 577545743-(2,3-Dihydro-benzo[1,4]dioxine-6-carbonyl)-1-(6-trifluoromethyl-pyridin-2-ylmethyl)-1H-quinolin-4-oneYield 18.8%

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 mg (0.228 mmol) and 71.1 mg (0.296 mmol) of 2-Bromomethyl-6-trifluoromethyl-pyridine, to give 20 mg of desired compound. LCMS (M+H)+: 467.1.

Sources & evidence

ORD record
ord-a307abfcf65e4143ba5a98e08a92a1d5
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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