Potassium Iodide → HCID 11990821, compound

HRID 2102681Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]([C:12]3[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[Cl:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22]Br.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:22][C:21]3[CH:24]=[CH:25][CH:26]=[C:19]([Cl:18])[CH:20]=3)([C:12]3[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of rac-6-chloro-3-(1-methyl-1H-pyrazol-4-yl)-1,3-dihydro-indol-2-one (0.1 g, 0.4 mmol) (from Example 14b supra), 3-chlorobenzyl bromide (0.098 g, 0.48 mmol) (Aldrich), potassium iodide (0.08 g, 0.481 mmol) and potassium carbonate (0.12 g, 0.87 mmol) in acetone (4 mL) was heated at 60° C. for 4 hours in a capped pressure tube. After cooling, the mixture was diluted with ethyl acetate and extracted with water and brine. Aqueous layers were back washed with ethyl acetate. Organic layers were combined, dried (Na2SO4), filtered and concentrated. The residue was purified by chromatography (ethyl acetate: dichloromethane, 1:1 V/V) to give rac-6-chloro-3-(3-chloro-benzyl)-3-[1-methyl-1H-pyrazol-4-yl]-1,3-dihydro-indol-2-one as a white solid. (Yield, 0.05 g, 33%).

Workup

temperatureAfter cooling
extractionextracted with water and brine
washAqueous layers were back washed with ethyl acetate
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe residue was purified by chromatography (ethyl acetate: dichloromethane, 1:1 V/V)

Sources & evidence

ORD record: ord-4970985ee7144b5ba200bcf0e93ebce8
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576082B2

Reaction notes

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