2-Bromopropionic acid → 2-[4-(5-Chloro-2-cyanophenyl)-5-(difluoromethyl)-2-oxopyridin-1(2H)-yl]propanoic acid

HRID 56729Notes

Reaction equation

HRID 56729 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]2[C:15]([CH:16]([F:18])[F:17])=[CH:14][NH:13][C:12](=[O:19])[CH:11]=2)[CH:3]=1.Br[CH:21]([CH3:25])[C:22]([OH:24])=[O:23]>>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]2[C:15]([CH:16]([F:17])[F:18])=[CH:14][N:13]([CH:21]([CH3:25])[C:22]([OH:24])=[O:23])[C:12](=[O:19])[CH:11]=2)[CH:3]=1

Participants

3

Reactant 2

HCID 117292-Bromopropionic acidHCID 1176049664-Chloro-2-[5-(difluoromethyl)-2-oxo-1,2-dihydropyridin-4-yl]benzonitrile

Product 1

HCID 1176229062-[4-(5-Chloro-2-cyanophenyl)-5-(difluoromethyl)-2-oxopyridin-1(2H)-yl]propanoic acid

Procedure

215 mg (purity 64%, 0.5 mmol) of 4-chloro-2-[5-(difluoromethyl)-2-oxo-1,2-dihydropyridin-4-yl]benzonitrile and 1.5 eq. of 2-bromopropanoic acid (racemate) were reacted according to General Method 4A at 50° C. Yield: 256 mg of crude product (purity 64%, 95% of theory)

Workup

  1. customaccording to General Method 4A at 50° C

Sources & evidence

ORD record
ord-2d4e3d63518749b3a07bf0a5c037787c
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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