Trifluoroacetic acid → 2-[4-(2-Bromo-5-chlorophenyl)-2-oxopyridin-1(2H)-yl]-3-(pyridin-4-yl)propanoic acid

HRID 56689Notes

Reaction equation

HRID 56689 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][N:12]([CH:15]([CH2:23][C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)[C:16]([O:18]C(C)(C)C)=[O:17])[C:11](=[O:30])[CH:10]=1.C(O)(C(F)(F)F)=O>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][N:12]([CH:15]([CH2:23][C:24]2[CH:25]=[CH:26][N:27]=[CH:28][CH:29]=2)[C:16]([OH:18])=[O:17])[C:11](=[O:30])[CH:10]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117622755tert-Butyl 2-[4-(2-bromo-5-chlorophenyl)-2-oxopyridin-1(2H)-yl]-3-(pyridin-4-yl)propanoate

Product 1

HCID 1176228752-[4-(2-Bromo-5-chlorophenyl)-2-oxopyridin-1(2H)-yl]-3-(pyridin-4-yl)propanoic acid

Procedure

1.7 g (purity 89%, 3.2 mmol) of tert-butyl 2-[4-(2-bromo-5-chlorophenyl)-2-oxopyridin-1(2H)-yl]-3-(pyridin-4-yl)propanoate (racemate) were hydrolysed with TFA according to General Method 6A. After work-up, the residue was triturated with diethyl ether and the solid was filtered off and dried under reduced pressure. Yield: 1.8 g (purity 76%, 99% of theory)

Workup

  1. customAfter work-up, the residue was triturated with diethyl ether
  2. filtrationthe solid was filtered off
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-eb0143d834014577a6db70778832725b
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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