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

HRID 56655Notes

Reaction equation

HRID 56655 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]([CH:8]([CH:14]([CH3:16])[CH3:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4](=[O:17])[CH:3]=1.[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([C:28]#[N:29])=[C:23](B(O)O)[CH:24]=1>>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:28]#[N:29])=[C:21]([C:2]2[CH:7]=[CH:6][N:5]([CH:8]([CH:14]([CH3:16])[CH3:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4](=[O:17])[CH:3]=2)[CH:20]=1

Participants

3

Reactant 2

HCID 467389345-Chloro-2-cyanophenylboronic acidHCID 117622680Ethyl 2-(4-bromo-2-oxopyridin-1(2H)-yl)-3-methylbutanoate

Product 1

HCID 117622646Ethyl 2-[4-(5-chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]-3-methylbutanoate

Procedure

240 mg (purity 92%, 0.73 mmol) of ethyl 2-(4-bromo-2-oxopyridin-1(2H)-yl)-3-methylbutanoate (racemate) and 172 mg (0.95 mmol) of 5-chloro-2-cyanophenylboronic acid in the presence of [1,1-bis(diphenylphosphino)ferrocene]palladium(II) chloride/monodichloromethane adduct were reacted according to General Method 2A. Yield: 117 mg (purity 81%, 36% of theory)

Sources & evidence

ORD record
ord-4a8deb7ad96640f09a7fa530f9ab9955
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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