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

HRID 56863Notes

Reaction equation

HRID 56863 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][CH2:17][C:18]([F:21])([F:20])[F:19])=[CH:14][NH:13][C:12](=[O:22])[CH:11]=2)[CH:3]=1.CC(C)([O-])C.CC(C)([O-])C.[Mg+2].CC(C)([O-])C.[K+].Br[CH:41]([CH3:45])[C:42]([OH:44])=[O:43]>>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]2[C:15]([O:16][CH2:17][C:18]([F:19])([F:20])[F:21])=[CH:14][N:13]([CH:41]([CH3:45])[C:42]([OH:44])=[O:43])[C:12](=[O:22])[CH:11]=2)[CH:3]=1

Participants

5

Reactant 4

HCID 117292-Bromopropionic acidHCID 12040442Magnesium 2-methylpropan-2-olateHCID 23665647Potassium tert-butoxideHCID 1176048274-Chloro-2-[2-oxo-5-(2,2,2-trifluoroethoxy)-1,2-dihydropyridin-4-yl]benzonitrile

Product 1

HCID 1176229802-[4-(5-Chloro-2-cyanophenyl)-2-oxo-5-(2,2,2-trifluoroethoxy)pyridin-1(2H)-yl]propanoic acid

Procedure

140 mg (purity 87%, 0.37 mmol) of 4-chloro-2-[2-oxo-5-(2,2,2-trifluoroethoxy)-1,2-dihydropyridin-4-yl]benzonitrile, 2.0 eq. of magnesium di-tert-butoxide, 1.05 eq. of potassium tert-butoxide and 1.5 eq. of 2-bromopropanoic acid (racemate) were reacted according to General Method 4A at 50° C. and, after aqueous work-up, used without purification for the next step. Yield: 214 mg (purity 73%, quant.)

Workup

  1. customaccording to General Method 4A at 50° C.
  2. customafter aqueous work-up, used without purification for the next step

Sources & evidence

ORD record
ord-f615f0520baa4c15a5147aae190e88f8
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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