Potassium Carbonate → N-(2,5-Dimethyl-2H-pyrazol-3-yl)-2-(2-oxo-2,3-dihydro-1H-indol-6-ylsulfanyl)-benzamide

HRID 2116795Notes

Reaction equation

HRID 2116795 reaction equation
C(=O)([O-])[O-].[K+].[K+].I[C:8]1[CH:16]=[C:15]2[C:11]([CH2:12][C:13](=[O:17])[NH:14]2)=[CH:10][CH:9]=1.[CH3:18][N:19]1[C:23]([NH:24][C:25](=[O:33])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[SH:32])=[CH:22][C:21]([CH3:34])=[N:20]1>[Cu]I>[CH3:18][N:19]1[C:23]([NH:24][C:25](=[O:33])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[S:32][C:8]2[CH:16]=[C:15]3[C:11]([CH2:12][C:13](=[O:17])[NH:14]3)=[CH:10][CH:9]=2)=[CH:22][C:21]([CH3:34])=[N:20]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 534188196-Iodo-2-oxindoleHCID 69144537N-(1,3-Dimethyl-1H-pyrazol-5-yl)-2-sulfanylbenzamide

Product 1

HCID 69128941N-(2,5-Dimethyl-2H-pyrazol-3-yl)-2-(2-oxo-2,3-dihydro-1H-indol-6-ylsulfanyl)-benzamideYield 52.3%

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
80 °C

Procedure

CuI (40 mg, 0.05 mmol), potassium carbonate (1.66 g, 12 mmol), 6-iodooxindole (as prepared in Preparation 1; 0.5 g, 1.93 mmol) and N-(2,5-Dimethyl-2H-pyrazol-3-yl)-2-mercapto-benzamide (as prepared in step 3 above; 0.477 g, 1.93 mmol) were added to a dry schlenk tube. The tube was evacuated and refilled with Ar(g) (3 times). Isopropanol (3.0 mL) and ethylene glycol (0.250 mL) were injected into the schlenk tube. The schlenk tube was sealed with a teflon valve and was heated to 80° C. and stirred for over 24 hours. Subsequently the reaction mixture was allowed to reach room temperature then diluted with EtOAc (˜20 mL) and water (˜10 mL). The mixture was acidified with 1 M HCl(aq) and the organics were separated and set aside. The aqueous phase was washed with EtOAc (2×20 mL). The organic layers were combined, dried over silica gel, filtered and concentrated in vacuo affording a yellow solid. The solid was then purified via flash silica gel chromatography (gradient eluant 10 to 40% EtOAc in Hexanes) affording the title compound as a pale yellow solid (0.379 g, 1.01 mmol, 52% yield).

Workup

  1. customThe tube was evacuated
  2. additionrefilled with Ar(g) (3 times)
  3. customThe schlenk tube was sealed with a teflon valve
  4. customto reach room temperature
  5. additionthen diluted with EtOAc (˜20 mL) and water (˜10 mL)
  6. customthe organics were separated
  7. washThe aqueous phase was washed with EtOAc (2×20 mL)
  8. customdried over silica gel
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customaffording a yellow solid
  12. customThe solid was then purified via flash silica gel chromatography (gradient eluant 10 to 40% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-4fba25a63077436eb85146e564cf839a
Source dataset
uspto-grants-2008_10
Patent number
US07439371B2

Reaction notes

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