Ethyl bromopyruvate → HCID 86721278, compound

HRID 1750436Notes

Reaction equation

HRID 1750436 reaction equation
[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[C:8]([C:18](=[S:20])[NH2:19])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:22][C:23](=O)[C:24]([O:26][CH2:27][CH3:28])=[O:25]>C(O)C>[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[C:8]([C:18]2[S:20][CH:22]=[C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[N:19]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 86721245HCID 86721245, compound

Product 1

HCID 86721278HCID 86721278, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-tert-butyl-5-(4-methoxyphenyl)-1H-pyrazole-4-carbothioamide (1.24 g, 4.28 mmol) and ethyl bromopyruvate (0.647 mL, 5.14 mmol) in ethanol (24 mL) was stirred at 90° C. for 14 hr. The reaction mixture was concentrated under reduced pressure, and hexane was added thereto to give ethyl 2-(1-(tert-butyl)-5-(4-methoxyphenyl)-1H-pyrazol-4-yl)thiazole-4-carboxylate (1.27 g, 3.29 mmol, 77%) as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and hexane
  2. additionwas added

Sources & evidence

ORD record
ord-28d55199f5044877b14b894dfd040879
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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