5-Chloro-2-(trifluoromethyl)phenylboronic acid → Ethyl 2-{4-[5-chloro-2-(trifluoromethyl)phenyl]-2-oxopyridin-1(2H)-yl}-3-cyclopropylpropanoate

HRID 56663Notes

Reaction equation

HRID 56663 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]([CH:8]([CH2:14][CH:15]2[CH2:17][CH2:16]2)[C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4](=[O:18])[CH:3]=1.[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([C:29]([F:32])([F:31])[F:30])=[C:24](B(O)O)[CH:25]=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:19][C:20]1[CH:21]=[CH:22][C:23]([C:29]([F:30])([F:31])[F:32])=[C:24]([C:2]2[CH:7]=[CH:6][N:5]([CH:8]([CH2:14][CH:15]3[CH2:17][CH2:16]3)[C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4](=[O:18])[CH:3]=2)[CH:25]=1

Participants

4

Reactant 2

HCID 467368175-Chloro-2-(trifluoromethyl)phenylboronic acidHCID 117622870Ethyl 2-(4-bromo-2-oxopyridin-1(2H)-yl)-3-cyclopropylpropanoate

Product 1

HCID 117622749Ethyl 2-{4-[5-chloro-2-(trifluoromethyl)phenyl]-2-oxopyridin-1(2H)-yl}-3-cyclopropylpropanoate

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

250 mg (0.8 mmol) of ethyl 2-(4-bromo-2-oxopyridin-1(2H)-yl)-3-cyclopropylpropanoate (racemate) and 214 mg (0.96 mmol) of 5-chloro-2-trifluoromethylphenylboronic acid in the presence of tetrakis(triphenylphosphine)palladium(0) were reacted according to General Method 2A. Yield: 35 mg (purity 87%, 9% of theory) of the title compound and 70 mg (22% of theory) of the product which is already hydrolysed (Example 6.1F)

Sources & evidence

ORD record
ord-6a2cf857d0c7401f9a68c29b8c5a1197
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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