Potassium Carbonate → HCID 71078166, compound

HRID 1774484Notes

Reaction equation

HRID 1774484 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([S:10][C:11]2[C:19]3[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=3)[NH:13][C:12]=2[CH3:21])[CH:7]=[N:6][CH:5]=1.Br[C:24]1[CH:25]=[N:26][N:27]([CH3:29])[CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1.CCOC(C)=O.[Cu]=O>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([S:10][C:11]2[C:19]3[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=3)[N:13]([C:24]3[CH:25]=[N:26][N:27]([CH3:29])[CH:28]=3)[C:12]=2[CH3:21])[CH:7]=[N:6][CH:5]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 1674331H-Pyrazole, 4-bromo-1-methyl-HCID 71077997HCID 71077997, compound

Product 1

HCID 71078166HCID 71078166, compound

Reagents, catalysts & solvents 3

HCID 14829Copper oxideCatalystHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

5-(6-Chloro-2-methyl-1H-indol-3-ylsulfanyl)-nicotinic acid methyl ester (0.100 g, 0.3 mmol), 4-bromo-1-methyl-1H-pyrazole (0.0966 mL, 0.9 mmol), copper(II) oxide (0.048 g, 0.6 mmol) and potassium carbonate (0.054 g, 0.39 mmol) were combined in pyridine (1 mL) in a sealed vial. The reaction was heated to 150° C. overnight then cooled, then diluted with EtOAc. The mixture was washed with HCl (1 M aq.) and brine, and the organic portion was dried and concentrated to yield the title compound as a crude mixture that was used directly in the next step.

Workup

  1. temperaturethen cooled
  2. washThe mixture was washed with HCl (1 M aq.) and brine
  3. customthe organic portion was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d1f4dfdf6cbc4b20a6e6c2afd10ee3cc
Source dataset
uspto-grants-2016_02
Patent number
US09260416B2

Reaction notes

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