Bromocyclopentane → HCID 69064639, compound

HRID 1817494Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:17]2[C:25]3[C:20](=[C:21]([C:26]([F:29])([F:28])[F:27])[CH:22]=[CH:23][CH:24]=3)[NH:19][N:18]=2)=[O:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH:32]1(Br)[CH2:36][CH2:35][CH2:34][CH2:33]1>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]([C:17]2[C:25]3[C:20](=[C:21]([C:26]([F:29])([F:27])[F:28])[CH:22]=[CH:23][CH:24]=3)[N:19]([CH:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)[N:18]=2)=[O:16])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

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.

Workup

customThe cool reaction mixture
customwas partitioned with EtOAc and 1 N HCl
washThe organic phase was washed with brine
dry with materialdried (Na2SO4)
customThe solvent was removed in vacuo
customThe resulting residue was purified by flash chromatography (silica gel, hexane-EtOAc, 9:1)

Sources & evidence

ORD record: ord-f7e40c01fad04fbd880ab9edc6b45643
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07598286B2

Reaction notes

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