Iodoethane → HCID 22288403, compound

HRID 1296466Notes

Reaction equation

HRID 1296466 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[NH:7][N:6]=[C:5]([C:8]2[S:12][C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:10][CH:9]=2)[CH:4]=1.[CH2:20](I)[CH3:21].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:20]([N:7]1[C:3]([C:2]([F:18])([F:1])[F:19])=[CH:4][C:5]([C:8]2[S:12][C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:10][CH:9]=2)=[N:6]1)[CH3:21]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 22288385HCID 22288385, compound

Product 1

HCID 22288403HCID 22288403, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 5-(5-trifluoromethyl-1H-pyrazol-3-yl)thiophene-2-carboxylate, ethyl iodide, potassium carbonate and DMF was stirred at room temperature for 9 hours. The residue obtained by a usual treatment was eluted by silica gel chromatography (eluent; n-hexane:ethyl acetate=15:1) to give ethyl 5-(1-ethyl-5-trifluoromethyl-1H-pyrazol-3-yl)thiophene-2-carboxylate as colorless needle crystals. Also, by changing the eluent of the silica gel chromatography to n-hexane:ethyl acetate=10:1, ethyl 5-(1-ethyl-3-trifluoromethyl-1H-pyrazol-5-yl)thiophene-2-carboxylate was obtained as a light yellow oil. By hydrolyzing these compounds with a base in the usual way, a) 5-(1-ethyl-5-trifluoromethyl-1H-pyrazol-3-yl)thiophene-2-carboxylic acid and b) 5-(1-ethyl-3-trifluoromethyl-1H-pyrazol-5-yl)thiophene-2-carboxylic acid were obtained.

Workup

  1. customThe residue obtained by a usual treatment
  2. washwas eluted by silica gel chromatography (eluent; n-hexane:ethyl acetate=15:1)

Sources & evidence

ORD record
ord-806dc80c6bd14b4ebc69d24b3b14f438
Source dataset
uspto-grants-2007_07
Patent number
US07247635B2

Reaction notes

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