5-Chloro-2-cyanophenylboronic acid → Ethyl 2-[4-(5-chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]-3-phenylpropanoate

HRID 56670Notes

Reaction equation

HRID 56670 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]([CH:8]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4](=[O:21])[CH:3]=1.[Cl:22][C:23]1[CH:24]=[CH:25][C:26]([C:32]#[N:33])=[C:27](B(O)O)[CH:28]=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:22][C:23]1[CH:28]=[CH:27][C:26]([C:32]#[N:33])=[C:25]([C:2]2[CH:7]=[CH:6][N:5]([CH:8]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4](=[O:21])[CH:3]=2)[CH:24]=1

Participants

4

Reactant 2

HCID 467389345-Chloro-2-cyanophenylboronic acidHCID 117622558Ethyl 2-(4-bromo-2-oxopyridin-1(2H)-yl)-3-phenylpropanoate

Product 1

HCID 117622559Ethyl 2-[4-(5-chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]-3-phenylpropanoate

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

572 mg (1.6 mmol) of ethyl 2-(4-bromo-2-oxopyridin-1(2H)-yl)-3-phenylpropanoate (racemate) and 330 mg (1.8 mmol) of 5-chloro-2-cyanophenylboronic acid in the presence of tetrakis(triphenylphosphine)palladium(0) were reacted according to General Method 2A. Yield: 300 mg (purity 94%, 43% of theory)

Sources & evidence

ORD record
ord-32bb918ced914e68973c9a55e8bb7444
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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