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

HRID 56648Notes

Reaction equation

HRID 56648 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]([CH:8]([CH3:16])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:4](=[O:17])[CH:3]=1.[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([C:28]([F:31])([F:30])[F:29])=[C:23](B(O)O)[CH:24]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([C:28]([F:29])([F:30])[F:31])=[C:23]([C:2]2[CH:7]=[CH:6][N:5]([CH:8]([CH3:16])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:4](=[O:17])[CH:3]=2)[CH:24]=1

Participants

4

Reactant 2

HCID 467368175-Chloro-2-(trifluoromethyl)phenylboronic acidHCID 117622807tert-Butyl 2-(4-bromo-2-oxopyridin-1(2H)-yl)propanoate

Product 1

HCID 117622679tert-Butyl 2-{4-[5-chloro-2-(trifluoromethyl)phenyl]-2-oxopyridin-1(2H)-yl}propanoate

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

2.0 g (6.4 mmol) of tert-butyl 2-(4-bromo-2-oxopyridin-1(2H)-yl)propanoate (racemate) and 1.7 g (7.7 mmol) of 5-chloro-2-(trifluoromethyl)phenylboronic acid in the presence of tetrakis(triphenylphosphine)palladium(0) were reacted according to General Method 2A. Yield: 2.3 g (purity 91%, 82% of theory)

Sources & evidence

ORD record
ord-f8233a728e694bc0b079076c904915a3
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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