Bromine → tert-Butyl 4-({2-[4-(5-chloro-2-cyanophenyl)-5-isopropoxy-2-oxopyridin-1(2H)-yl]propanoyl}amino)benzoate

HRID 56754Notes

Reaction equation

HRID 56754 reaction equation
I[C:2]1[C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:6][N:5]([CH:12]([CH3:29])[C:13]([NH:15][C:16]2[CH:28]=[CH:27][C:19]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[CH:18][CH:17]=2)=[O:14])[C:4](=[O:30])[CH:3]=1.BrBr.[Cl:33][C:34]1[CH:35]=[CH:36][C:37]([C:43]#[N:44])=[C:38](B(O)O)[CH:39]=1>>[Cl:33][C:34]1[CH:39]=[CH:38][C:37]([C:43]#[N:44])=[C:36]([C:2]2[C:7]([O:8][CH:9]([CH3:10])[CH3:11])=[CH:6][N:5]([CH:12]([CH3:29])[C:13]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([C:20]([O:22][C:23]([CH3:26])([CH3:24])[CH3:25])=[O:21])=[CH:27][CH:28]=3)=[O:14])[C:4](=[O:30])[CH:3]=2)[CH:35]=1

Participants

4

Reactant 3

HCID 24408BromineHCID 467389345-Chloro-2-cyanophenylboronic acidHCID 117622845tert-butyl 4-({2-[4-iodo-2-oxo-5-(propan-2-yloxy)pyridin-1(2H)-yl]propanoyl}amino)benzoate

Product 1

HCID 117622846tert-Butyl 4-({2-[4-(5-chloro-2-cyanophenyl)-5-isopropoxy-2-oxopyridin-1(2H)-yl]propanoyl}amino)benzoate

Procedure

100 mg of a mixture (3:1) of tert-butyl 4-({2-[4-iodo-2-oxo-5-(propan-2-yloxy)pyridin-1(2H)-yl]propanoyl}amino)benzoate (racemate) and the analogous bromine compound and 41 mg (0.23 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: 31 mg (29% of theory)

Sources & evidence

ORD record
ord-417c82575d98446eb09be3f6433655f9
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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