5-Chloro-2-(trifluoromethyl)phenylboronic acid → Ethyl {4-[5-chloro-2-(trifluoromethyl)phenyl]-2-oxopyridin-1(2H)-yl}acetate

HRID 56673Notes

Reaction equation

HRID 56673 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4](=[O:14])[CH:3]=1.[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([C:25]([F:28])([F:27])[F:26])=[C:20](B(O)O)[CH:21]=1>>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([C:25]([F:26])([F:27])[F:28])=[C:20]([C:2]2[CH:7]=[CH:6][N:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4](=[O:14])[CH:3]=2)[CH:21]=1

Participants

3

Reactant 2

HCID 467368175-Chloro-2-(trifluoromethyl)phenylboronic acidHCID 71009808Ethyl 2-(4-bromo-2-oxopyridin-1(2H)-YL)acetate

Product 1

HCID 117622823Ethyl {4-[5-chloro-2-(trifluoromethyl)phenyl]-2-oxopyridin-1(2H)-yl}acetate

Procedure

2.04 g (7.8 mmol) of ethyl (4-bromo-2-oxopyridin-1(2H)-yl)acetate and 1.98 g (8.6 mmol) of 5-chloro-2-trifluoromethylphenylboronic acid in the presence of [1,1-bis(diphenylphosphino)ferrocene]palladium(II) chloride/dichloromethane monoadduct were reacted according to General Method 2A. Yield: 2.89 g (quant.)

Sources & evidence

ORD record
ord-cf808488f41d45298c92203087c7c70a
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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