Pyrazole → HCID 67973369, compound

HRID 925402Notes

Reaction equation

HRID 925402 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][NH:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1I.[NH:23]1[CH:27]=[CH:26][CH:25]=[N:24]1.C(=O)([O-])[O-].[K+].[K+]>CC(O)C.[Cu]I>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][NH:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:23]1[CH:27]=[CH:26][CH:25]=[N:24]1

Participants

6

Reactant 3

HCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 17271791N-(2-(5-chloro-1H-indol-3-yl)ethyl)-2-iodobenzamide

Product 1

HCID 67973369HCID 67973369, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of N-(2-(5-chloro-1H-indol-3-yl)ethyl)-2-iodobenzamide (0.080 g; 0.188 mmol), 1H-pyrazole (0.065 g; 0.942 mmol), copper (I) iodide (0.0036 g; 0.002 mmol), and potassium carbonate (0.032 g; 0.226 mmol) in 2-propanol (3 ml) was irradiated in a microwave oven microwave for 20 minutes at 150° C. The volatiles were removed under reduced pressure and the residue was partitioned between water and ethyl acetate. The aqueous layer was then extracted several times with ethyl acetate. The combined organic layers were evaporated to dryness and the residue was purified by flash chromatography on silica gel (eluent 1 to 10% methanol in dichloromethane) to afford 0.028 g (41%) of N-(2-(5-Chloro-1H-indol-3-yl)ethyl)-2-(1H-pyrazol-1-yl)benzamide as a white solid.

Workup

  1. customwas irradiated in a microwave oven microwave for 20 minutes at 150° C
  2. customThe volatiles were removed under reduced pressure
  3. customthe residue was partitioned between water and ethyl acetate
  4. extractionThe aqueous layer was then extracted several times with ethyl acetate
  5. customThe combined organic layers were evaporated to dryness
  6. customthe residue was purified by flash chromatography on silica gel (eluent 1 to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-5fb1f00c3c7e49d0bcfb4ede8bb37429
Source dataset
uspto-grants-2016_03
Patent number
US09284271B2

Reaction notes

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