Iodoethane → 6-Ethoxypyrazolo[5,1-b][1,3]thiazole-7-carboxylic acid ethyl ester

HRID 41263Notes

Reaction equation

HRID 41263 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:14])[NH:8][N:9]2[CH:13]=[CH:12][S:11][C:10]=12)=[O:5])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:22][CH3:23]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:14][CH2:22][CH3:23])=[N:8][N:9]2[CH:13]=[CH:12][S:11][C:10]=12)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 58223469HCID 58223469, compound

Product 1

HCID 582234016-Ethoxypyrazolo[5,1-b][1,3]thiazole-7-carboxylic acid ethyl esterYield 72.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a DMF (119 mL) solution of 6-oxo-5,6-dihydro-pyrazolo[5,1-b][1,3]thiazole-7-carboxylic acid ethyl ester (8.5 g, 40.2 mmol), cesium carbonate (26.1 g, 80.2 mmol) and iodoethane (8.3 mL, 80.2 mmol) were added while stirring at room temperature. The mixture was stirred at room temperature for one hour, was extracted with diethyl ether, washed with brine, and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by medium pressure amino silica gel column chromatography (n-heptane/ethyl acetate: 10% then 40%) to obtain the title compound (7.01 g, 29.2 mmol).

Workup

  1. stirringThe mixture was stirred at room temperature for one hour
  2. extractionwas extracted with diethyl ether
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by medium pressure amino silica gel column chromatography (n-heptane/ethyl acetate

Sources & evidence

ORD record
ord-1b1b7a61f1e3475d91e37f9133e17f03
Source dataset
uspto-grants-2013_09
Patent number
US08530504B2

Reaction notes

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