Ethyl bromopyruvate → HCID 25232519, compound

HRID 419906Notes

Reaction equation

HRID 419906 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[S:14][C:13]([NH2:15])=[N:12][CH:11]=1)([O-:3])=[O:2].Br[CH2:17][C:18](=O)[C:19]([O:21][CH2:22][CH3:23])=[O:20]>C(C(C)=O)C>[CH2:22]([O:21][C:19]([C:18]1[N:15]=[C:13]2[N:12]([CH:17]=1)[CH:11]=[C:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])[S:14]2)=[O:20])[CH3:23]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 25232518HCID 25232518, compound

Product 1

HCID 25232519HCID 25232519, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

5-(2-Nitro-phenyl)-thiazol-2-ylamine (100 mg, 0.452 mmol) was mixed with 10 mL of methyl ethyl ketone along with 1.5 equivalents of ethyl bromopyruvate. The reaction mixture was stirred under reflux for 5 hours. The reaction mixture was cooled to room temperature and concentrated. The crude product was purified by chromatography (Isco, gradient elution, CH2Cl2 to 9:1 CH2Cl2/MeOH) to afford 60 mg of 2-(2-nitro-phenyl)-imidazo[2,1-b]thiazole-6-carboxylic acid ethyl ester (MS, M++H=318).

Workup

  1. temperatureunder reflux for 5 hours
  2. concentrationconcentrated
  3. customThe crude product was purified by chromatography (Isco, gradient elution, CH2Cl2 to 9:1 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-43a5a83619ae4c6c8347297dd30b098d
Source dataset
uspto-grants-2012_01
Patent number
US08093401B2

Reaction notes

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