Ethyl bromopyruvate → ethyl 2-(1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl)thiazole-4-carboxylate

HRID 1750363Notes

Reaction equation

HRID 1750363 reaction equation
[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[C:8]([C:17](=[S:19])[NH2:18])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:21][C:22](=O)[C:23]([O:25][CH2:26][CH3:27])=[O:24]>C(O)C>[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[C:8]([C:17]2[S:19][CH:21]=[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:18]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 867211801-tert-butyl-5-(4-fluorophenyl)-1H-pyrazole-4-carbothioamide

Product 1

HCID 86721201ethyl 2-(1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl)thiazole-4-carboxylateYield 64.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the compound (710 mg, 2.56 mmol) obtained in Example 1, step 4 and ethyl bromopyruvate (0.322 mL, 2.56 mmol) in ethanol (15 mL) was stirred at 80° C. for 16 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (solvent gradient; 3→50% ethyl acetate/hexane) to give ethyl 2-(1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl)thiazole-4-carboxylate (50 mg, 0.108 mmol, 64.6%) as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (solvent gradient; 3→50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3666247fc3554d31badf63b39a53dbca
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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