Trifluoroacetic acid → 2-(Pyridin-2-yl)-1,3-thiazole-4-carboxylic acid

HRID 539653Notes

Reaction equation

HRID 539653 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[S:8][CH:9]=[C:10]([C:12]([O:14]C(C)(C)C)=[O:13])[N:11]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[S:8][CH:9]=[C:10]([C:12]([OH:14])=[O:13])[N:11]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67450476HCID 67450476, compound

Product 1

HCID 156230902-(Pyridin-2-yl)-1,3-thiazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 2-(pyridin-2-yl)thiazole-4-carboxylate 7.3 (340 mg, 1.3 mmol) in commercial anhydrous CH2Cl2 (5 mL) at RT was added TFA (0.93 mL, 13 mmol) under N2. The mixture was stirred at RT overnight. The mixture was diluted with CH2Cl2 (25 mL), washed with an aqueous solution of NaHSO3 10% (5×25 mL), brine (25 mL) and then water (25 mL). The organic layer was dried over MgSO4 and evaporated to afford title product as a yellow oil. Yield: 250 mg (94%). LCMS: P=93%, rt=3.03 nm, m/z=207.

Workup

  1. washwashed with an aqueous solution of NaHSO3 10% (5×25 mL), brine (25 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. customevaporated

Sources & evidence

ORD record
ord-976bc365d20d47cda2d357cf59f7b5a5
Source dataset
uspto-grants-2014_10
Patent number
US08871761B2

Reaction notes

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