2-Bromopropionic acid → 2-[4-(5-Chloro-2-cyanophenyl)-2-oxo-5-(trifluoromethyl)pyridin-1(2H)-yl]propanoic acid

HRID 56733Notes

Reaction equation

HRID 56733 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]2[C:15]([C:16]([F:19])([F:18])[F:17])=[CH:14][NH:13][C:12](=[O:20])[CH:11]=2)[CH:3]=1.Br[CH:22]([CH3:26])[C:23]([OH:25])=[O:24]>>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]2[C:15]([C:16]([F:17])([F:18])[F:19])=[CH:14][N:13]([CH:22]([CH3:26])[C:23]([OH:25])=[O:24])[C:12](=[O:20])[CH:11]=2)[CH:3]=1

Participants

3

Reactant 2

HCID 117292-Bromopropionic acidHCID 1176056274-Chloro-2-[2-oxo-5-(trifluoromethyl)-1,2-dihydropyridin-4-yl]benzonitrile

Product 1

HCID 1176227202-[4-(5-Chloro-2-cyanophenyl)-2-oxo-5-(trifluoromethyl)pyridin-1(2H)-yl]propanoic acid

Procedure

456 mg (purity 86%, 1.31 mmol) of 4-chloro-2-[2-oxo-5-(trifluoromethyl)-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: 515 mg (purity 51%, 54% of theory)

Workup

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

Sources & evidence

ORD record
ord-11e610a21c7140f09d3502d157f66e5d
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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