Chlorotrimethylsilane → Methyl 2-(pyridin-2-yl)thiazole-4-carboxylate

HRID 539654Notes

Reaction equation

HRID 539654 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]([OH:14])=[O:13])[N:11]=1.[Si](Cl)(C)(C)[CH3:16]>CO>[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][CH3:16])=[O:13])[N:11]=1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 156230902-(Pyridin-2-yl)-1,3-thiazole-4-carboxylic acid

Product 1

HCID 57688390Methyl 2-(pyridin-2-yl)thiazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-(pyridin-2-yl)thiazole-4-carboxylic acid 7.4 (500 mg, 2.425 mmol) in commercial anhydrous methanol (10 mL) was added TMS-Cl (0.77 mL, 6.06 mmol) at once. The RM was heated to 50° C. overnight. The RM. was concentrated under reduced pressure and the residue was used crude in next step. Yield: 649 mg (quantitative). LCMS: P=94%, rt=4.07 nm, m/z=221.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customP=94%, rt=4.07 nm, m/z=221

Sources & evidence

ORD record
ord-f6020b528dc1424eaa9182b681f7e14c
Source dataset
uspto-grants-2014_10
Patent number
US08871761B2

Reaction notes

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