2-(Bromomethyl)-6-(trifluoromethyl)pyridine → 3-(4-Methoxy-3-methyl-benzoyl)-1-(6-trifluoromethyl-pyridin-2-ylmethyl)-1H-[1,8]naphthyridin-4-one

HRID 227135Notes

Reaction equation

HRID 227135 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([C:7]([C:9]2[C:18](=[O:19])[C:17]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[NH:11][CH:10]=2)=[O:8])=[CH:5][C:4]=1[CH3:22].Br[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[N:26]=1>>[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([C:7]([C:9]2[C:18](=[O:19])[C:17]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:33])([F:32])[F:34])[N:26]=3)[CH:10]=2)=[O:8])=[CH:5][C:4]=1[CH3:22]

Participants

3

Reactant 2

HCID 469414632-(Bromomethyl)-6-(trifluoromethyl)pyridineHCID 577545283-(4-Methoxy-3-methyl-benzoyl)-1H-[1,8]naphthyridin-4-one

Product 1

HCID 577546853-(4-Methoxy-3-methyl-benzoyl)-1-(6-trifluoromethyl-pyridin-2-ylmethyl)-1H-[1,8]naphthyridin-4-oneYield 18.2%

Procedure

Experimental conditions analogous to those described for Step 3 of Example 1, from 50 mg (0.17 mmol) of 3-(4-Methoxy-3-methyl-benzoyl)-1H-[1,8]naphthyridin-4-one, and 2-Bromomethyl-6-trifluoromethyl-pyridine 53 mg (0.22 mmol), to give 14 mg of desired compound. LCMS (M+H)+: 454.1.

Sources & evidence

ORD record
ord-5b58e32923f54c7f880c1d3a4c376058
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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