Trifluoroacetic acid → 2-(2',3-Difluoro-2,4'-bipyridin-5-yl)acetic acid

HRID 592233Notes

Reaction equation

HRID 592233 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[C:13]([F:14])=[CH:12][C:11]([CH2:15][C:16]([O:18]C(C)(C)C)=[O:17])=[CH:10][N:9]=2)[CH:5]=[CH:4][N:3]=1.C(O)(C(F)(F)F)=O.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([C:8]2[C:13]([F:14])=[CH:12][C:11]([CH2:15][C:16]([OH:18])=[O:17])=[CH:10][N:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 58447733Tert-butyl 2-(2',3-difluoro-2,4'-bipyridin-5-yl)acetate

Product 1

HCID 584477862-(2',3-Difluoro-2,4'-bipyridin-5-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl 2-(2′,3-difluoro-2,4′-bipyridin-5-yl)acetate 205-5 (248 mg, 0.81 mmol) and TFA (0.8 mL) in DCM (0.8 mL) was stirred at room temperature for 3 hours. The solution was adjusted to pH around 12 by Na2CO3 and extracted with dichloromethane. The aqueous phase was acidified to pH 3 by 1N HCl aqueous solution and stirred for 15 minutes. The solvents were evaporated and the remaining solid was extracted with 20% methanol in ethyl acetate and filtered to remove the insoluble. The filtrate was concentrated to dryness by rotary evaporation to give 2-(2′,3-difluoro-2,4′-bipyridin-5-yl)acetic acid 205-6, which was used directly for next step. MS m/z 251.1 (M+1).

Workup

  1. extractionextracted with dichloromethane
  2. stirringstirred for 15 minutes
  3. customThe solvents were evaporated
  4. extractionthe remaining solid was extracted with 20% methanol in ethyl acetate
  5. filtrationfiltered
  6. customto remove the insoluble
  7. concentrationThe filtrate was concentrated to dryness by rotary evaporation

Sources & evidence

ORD record
ord-d283d47421244f2fb13231360794fad6
Source dataset
uspto-grants-2016_01
Patent number
US09238646B2

Reaction notes

Loading…