diethyl 1H-pyrazole-3,5-dicarboxylate → HCID 69069671, compound

HRID 733150Notes

Reaction equation

HRID 733150 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:8][N:7]=1)=[O:5])[CH3:2].[Br:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1>ClCCl>[CH2:14]([O:13][C:11]([C:9]1[CH:10]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[N:7]([C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([Br:16])[CH:22]=2)[N:8]=1)=[O:12])[CH3:15]

Participants

4

Reactant 2

HCID 142184diethyl 1H-pyrazole-3,5-dicarboxylateHCID 2734318(3-Bromophenyl)boronic acid

Product 1

HCID 69069671HCID 69069671, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of diethyl-3,5-pyrazoledicarboxylate (1.0 g, 4.71 mmol), 3-bromophenylboronicacid (1.89 g, 9.42 mmol) and di-Micron-hydroxo-bis[(N,N,N′,N′-tetramethylethylenediamine)copper(II)]chloride (0.21 g, 0.47 mmol) in dichloromethane (22 mL) was stirred under air for 36 hours under air. It was filtered over a short silica gel pad, concentrated and purified by column chromatography (hexanes:ethyl acetate; 90:10) to yield 1.45 g (85%) of the product as a white solid.

Workup

  1. filtrationIt was filtered over a short silica gel pad
  2. concentrationconcentrated
  3. custompurified by column chromatography (hexanes:ethyl acetate; 90:10)

Sources & evidence

ORD record
ord-7480a34b17a9477a8d625043eab92eea
Source dataset
uspto-grants-2009_09
Patent number
US07589116B2

Reaction notes

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