Acetate → 1-(1H-indol-5-yl)-3-methyl-pyrazole-4-carboxylic acid ethyl ester

HRID 1026611Notes

Reaction equation

HRID 1026611 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:11])=[N:8][NH:9][CH:10]=1)=[O:5])[CH3:2].[NH:12]1[C:20]2[C:15](=[CH:16][C:17](B(O)O)=[CH:18][CH:19]=2)[CH:14]=[CH:13]1.C([O-])(=O)C.N1C=CC=CC=1>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:11])=[N:8][N:9]([C:17]2[CH:16]=[C:15]3[C:20](=[CH:19][CH:18]=2)[NH:12][CH:13]=[CH:14]3)[CH:10]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 175AcetateHCID 1049PyridineHCID 27343615-Indolylboronic acidHCID 178469911HCID 178469911, compound

Product 1

HCID 671070191-(1H-indol-5-yl)-3-methyl-pyrazole-4-carboxylic acid ethyl esterYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Methyl-1H-pyrazole-4-carboxylic acid ethyl ester (1.43 g, 9.27 mmol) and 1H-indol-5-ylboronic acid (1.50 g, 9.29 mmol) were dissolved in N,N-dimethylformamide (93 mL). Cupper (II) acetate (1.27 g, 6.98 mmol) and pyridine (1.50 mL, 18.5 mmol) were added, and the mixture was stirred for 3 days at room temperature. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography to give the title compound (1.2433 g, 4.62 mmol, 50% Yield).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-cd3e1af2ac52474b805a3a4c68154c49
Source dataset
uspto-grants-2014_05
Patent number
US08729273B2

Reaction notes

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