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

HRID 56658Notes

Reaction equation

HRID 56658 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]([CH:8]([CH2:14][CH2:15][CH2:16][CH3:17])[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]#[N:30])=[C:24](B(O)O)[CH:25]=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]([CH2:14][CH2:15][CH2:16][CH3:17])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4](=[O:18])[CH:3]=2)[CH:21]=1

Participants

3

Reactant 2

HCID 467389345-Chloro-2-cyanophenylboronic acidHCID 117622881Ethyl 2-(4-iodo-2-oxopyridin-1(2H)-yl)hexanoate

Product 1

HCID 117622689Ethyl 2-[4-(5-chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]hexanoate

Procedure

150 mg (0.41 mmol) of ethyl 2-(4-iodo-2-oxopyridin-1(2H)-yl)hexanoate (racemate) and 97 mg (0.53 mmol) of 5-chloro-2-cyanophenylboronic acid in the presence of [1,1-bis(diphenylphosphino)ferrocene]palladium(II) chloride/dichloromethane monoadduct were reacted according to General Method 2A. Yield: 114 mg (purity 95%, 70% of theory)

Sources & evidence

ORD record
ord-28b76e6515d14df6b8c23a7fd3699f0a
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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