Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Iodide | HCID 4875 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 1-(Bromomethyl)-3-chlorobenzene | HCID 69838 | — |
| Reactant | HCID 57803072 | HCID 57803072 | — |
| Solvent | Acetone | HCID 180 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 11990821 | HCID 11990821 | — |
Reaction Steps
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%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07576082B2 |
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| Source dataset | uspto-grants-2009_08 |
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| ORD ID | ord-4970985ee7144b5ba200bcf0e93ebce8 |
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| Source note | uspto-grants-2009_08 |
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