Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Bromocyclopentane | HCID 8728 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 178519713 | HCID 178519713 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 69064639 | HCID 69064639 | 73.3% |
Reaction Steps
To a solution of [4-(benzyloxy)phenyl](7-trifluoromethyl-1H-indazol-3-yl)methanone (0.372 g, 0.94 mmol) in 3 mL DMF was added in one portion sodium hydride (0.044 g, 1.1 mmol, 60% in oil). After the gas evolution ceased, cyclopentyl bromide (0.118 mL, 1.1 mmol) was added and the reaction was stirred at ambient to 50° C. for 24 hours. The cool reaction mixture was partitioned with EtOAc and 1 N HCl. The organic phase was washed with brine and dried (Na2SO4). The solvent was removed in vacuo. The resulting residue was purified by flash chromatography (silica gel, hexane-EtOAc, 9:1) to give 0.320 g of the title compound as a yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07598286B2 |
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| Source dataset | uspto-grants-2009_10 |
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| ORD ID | ord-f7e40c01fad04fbd880ab9edc6b45643 |
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| Source note | uspto-grants-2009_10 |
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