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

HRID 56714

Reaction equation

HRID 56714 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:17]#[N:18])=[C:6]([C:8]2[C:9]([C:15]#[N:16])=[CH:10][NH:11][C:12](=[O:14])[CH:13]=2)[CH:7]=1.Br[CH:20]([CH3:24])[C:21]([OH:23])=[O:22]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:17]#[N:18])=[C:6]([C:8]2[C:9]([C:15]#[N:16])=[CH:10][N:11]([CH:20]([CH3:24])[C:21]([OH:23])=[O:22])[C:12](=[O:14])[CH:13]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 117292-Bromopropionic acidHCID 1176056654-(5-Chloro-2-cyanophenyl)-6-oxo-1,6-dihydropyridin-3-carbonitrile

Product 1

HCID 1176227652-[4-(5-Chloro-2-cyanophenyl)-5-cyano-2-oxopyridin-1(2H)-yl]propanoic acid

Procedure

312 mg (purity 91%, 1.11 mmol) of 4-(5-chloro-2-cyanophenyl)-6-oxo-1,6-dihydropyridin-3-carbonitrile and 1.5 eq. of 2-bromopropanoic acid (racemate) were reacted according to General Method 4A at 45° C. Yield: 240 mg (purity 85%, 56% of theory)

Workup

  1. customaccording to General Method 4A at 45° C

Sources & evidence

ORD record
ord-18db1e831c1f4d97889247fdc84cacdc
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Linked notes

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