Tetrahydrofuran → HCID 66552418, compound

HRID 1615869Notes

Reaction equation

HRID 1615869 reaction equation
CS[C:3]1[S:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[C:7]([C:12]1[CH:13]=[C:14]([CH:20]=[CH:21][CH:22]=1)[C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:6]=2.O[O:24][S:25]([O-:27])=O.[K+].[CH2:29]1COCC1>CO.O>[CH3:29][S:25]([C:3]1[S:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[C:7]([C:12]1[CH:13]=[C:14]([CH:20]=[CH:21][CH:22]=1)[C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:6]=2)(=[O:27])=[O:24]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 66552415Benzoic acid, 3-[2-(methylthio)thiazolo[5,4-b]pyridin-5-yl]-, ethyl ester

Product 1

HCID 66552418HCID 66552418, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution was ethyl 3-(2-(methylthio)thiazolo[5,4-b]pyridin-5-yl)benzoate (5.6 g, 16.9 mmol) in THF (25 mL) and methanol (25 mL) was added Oxone (41.55 g, 67.67 mmol) in water (25 mL). The reaction mixture was stirred for 16 hours at room temperature. The reaction mixture was filtered and concentrated to give 5.8 g (94%, yield) of ethyl 3-(2-(methylsulfonyl)thiazolo[5,4-b]pyridin-5-yl)benzoate as a bright brown solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-7ae68220088142938b442c736dfc5258
Source dataset
uspto-grants-2014_07
Patent number
US08765747B2

Reaction notes

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