5-Chloro-2-cyanophenylboronic acid → tert-Butyl 2-[4-(5-chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]butanoate

HRID 56652Notes

Reaction equation

HRID 56652 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]([CH:8]([CH2:16][CH3:17])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:4](=[O:18])[CH:3]=1.[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([C:29]#[N: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:25]=[CH:24][C:23]([C:29]#[N:30])=[C:22]([C:2]2[CH:7]=[CH:6][N:5]([CH:8]([CH2:16][CH3:17])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:4](=[O:18])[CH:3]=2)[CH:21]=1

Participants

4

Reactant 2

HCID 467389345-Chloro-2-cyanophenylboronic acidHCID 117622861tert-Butyl 2-(4-bromo-2-oxopyridin-1(2H)-yl)butanoate

Product 1

HCID 117622863tert-Butyl 2-[4-(5-chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]butanoate

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

600 mg (purity 82%, 1.56 mmol) of tert-butyl 2-(4-bromo-2-oxopyridin-1(2H)-yl)butanoate (racemate) and 325 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: 543 mg (purity 59%, 55% of theory)

Sources & evidence

ORD record
ord-9a2de717170042578cf19f1175aeef13
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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