Trifluoroacetic acid → 2-(5-fluoro-6-(1H-tetrazol-1-yl)pyridin-3-yl)acetic acid

HRID 1502161Notes

Reaction equation

HRID 1502161 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:13][C:14]([O:16]C(C)(C)C)=[O:15])[CH:5]=[N:6][C:7]=1[N:8]1[CH:12]=[N:11][N:10]=[N:9]1.C1(SC)C=CC=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH2:13][C:14]([OH:16])=[O:15])[CH:5]=[N:6][C:7]=1[N:8]1[CH:12]=[N:11][N:10]=[N:9]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7520ThioanisoleHCID 89619238tert-butyl 2-(5-fluoro-6-(1H-tetrazol-1-yl)pyridin-3-yl)acetate

Product 1

HCID 896188352-(5-fluoro-6-(1H-tetrazol-1-yl)pyridin-3-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl 2-(5-fluoro-6-(1H-tetrazol-1-yl)pyridin-3-yl)acetate (70 mg, 0.25 mmol) in DCM (0.50 mL) was added thioanisole (163 μl, 1.38 mmol) and TFA (241 μl, 3.13 mmol) at 0° C. The reaction mixture was stirred at rt for 5 h. The reaction mixture was concentrated to give the crude product, which was used in the next step without further purification: LC/MS: [(M+1-28)]+=196.5.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-d186d33210f640289317907b4f0dec50
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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