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Water → 4-(2-cyclopentyl-7-fluoro-2H-indazol-3-yl)phenol

HRID 735433
Notes
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Reaction equation

HRID 735433 reaction equation
[CH:1]1([N:6]2[C:14]([C:15]3[CH:20]=[CH:19][C:18]([O:21]C)=[CH:17][CH:16]=3)=[C:13]3[C:8]([C:9]([F:23])=[CH:10][CH:11]=[CH:12]3)=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C1CCCCC=1.B(Br)(Br)Br.O>C(Cl)Cl>[CH:1]1([N:6]2[C:14]([C:15]3[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=3)=[C:13]3[C:8]([C:9]([F:23])=[CH:10][CH:11]=[CH:12]3)=[N:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8079CyclohexeneHCID 25134Boron tribromideHCID 115005622-cyclopentyl-7-fluoro-3-(4-methoxyphenyl)-2H-indazole

Product 1

HCID 1354539644-(2-cyclopentyl-7-fluoro-2H-indazol-3-yl)phenolYield 57.2%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

A solution of 2-cyclopentyl-7-fluoro-3-(4-methoxyphenyl)-2H-indazole (0.055 g, 0.177 mmol) in CH2Cl2 containing excess equivalents of cyclohexene (0.3 mL) at −78° C. was treated with boron tribromide (0.70 mL, 0.74 mmol, 4 eq.) and slowly allowed to warm to ambient temperature. The reaction mixture was quenched by dropwise addition of CH3OH to the cooled reaction mixture. The solvent was removed in vacuo and the residue partitioned with EtOAc and 1 N HCl. The organic phase was washed with brine and dried (Na2SO4). Removal of the solvent in vacuo afforded the crude product. Pure product was obtained by crystallization or flash chromatography through water deactivated silica gel to give the product (0.03 g) as an amber solid.

Workup

  1. customThe reaction mixture was quenched by dropwise addition of CH3OH to the cooled reaction mixture
  2. customThe solvent was removed in vacuo
  3. customthe residue partitioned with EtOAc and 1 N HCl
  4. washThe organic phase was washed with brine
  5. dry with materialdried (Na2SO4)
  6. customRemoval of the solvent in vacuo
  7. customafforded the crude product

Sources & evidence

ORD record
ord-76d38e7eb9f74ed18332b4ace7d15f51
Source dataset
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07592363B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes