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

HRID 56737Notes

Reaction equation

HRID 56737 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]2[C:15]([O:16][CH3:17])=[CH:14][NH:13][C:12](=[O:18])[CH:11]=2)[CH:3]=1.Br[CH:20]([CH3:24])[C:21]([OH:23])=[O:22]>>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]2[C:15]([O:16][CH3:17])=[CH:14][N:13]([CH:20]([CH3:24])[C:21]([OH:23])=[O:22])[C:12](=[O:18])[CH:11]=2)[CH:3]=1

Participants

3

Reactant 2

HCID 117292-Bromopropionic acidHCID 1176049354-Chloro-2-(5-methoxy-2-oxo-1,2-dihydropyridin-4-yl)benzonitrile

Product 1

HCID 1176225622-[4-(5-Chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]propanoic acid

Procedure

599 mg (purity 87%, 2.00 mmol) of 4-chloro-2-(5-methoxy-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 90° C. Yield: 716 mg (purity 68%, 73% of theory)

Workup

  1. customaccording to General Method 4A at 90° C

Sources & evidence

ORD record
ord-afb35997ec8d45ffb4ad667a45a6b837
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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