Ethyl 4-chloroacetoacetate → HCID 86721242, compound

HRID 1750398Notes

Reaction equation

HRID 1750398 reaction equation
[Br:1][C:2]1[N:6]([C:7]([CH3:10])([CH3:9])[CH3:8])[N:5]=[CH:4][C:3]=1[C:11](=[S:13])[NH2:12].Cl[CH2:15][C:16](=O)[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>C(O)C>[Br:1][C:2]1[N:6]([C:7]([CH3:8])([CH3:9])[CH3:10])[N:5]=[CH:4][C:3]=1[C:11]1[S:13][CH:15]=[C:16]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:12]=1

Participants

4

Reactant 2

HCID 69484Ethyl 4-chloroacetoacetateHCID 86721241HCID 86721241, compound

Product 1

HCID 86721242HCID 86721242, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the compound (2.80 g, 10.68 mmol) obtained in step 5 and ethyl 4-chloroacetoacetate (1.588 mL, 11.75 mmol) in ethanol (30 mL) was stirred at 80° C. for 16 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by NH-silica gel column chromatography (solvent gradient; 3→50% ethyl acetate/hexane) to give ethyl 2-(2-(5-bromo-1-tert-butyl-1H-pyrazol-4-yl)thiazol-4-yl)acetate (2.55 g, 6.85 mmol, 64%) as a colorless oil

Workup

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

Sources & evidence

ORD record
ord-5a88134361ac4aa2b5655379b9aa6102
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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