Borane;tetrahydrofuran → HCID 67131197, compound

HRID 1678658Notes

Reaction equation

HRID 1678658 reaction equation
B.O1CCCC1.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:22]([CH:23]([CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[C:24](O)=[O:25])=[C:21]3[C:16]([CH:17]=[CH:18][CH:19]=[CH:20]3)=[N:15]2)=[CH:10][CH:9]=1>C1COCC1>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:22]([CH:23]([CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[CH2:24][OH:25])=[C:21]3[C:16]([CH:17]=[CH:18][CH:19]=[CH:20]3)=[N:15]2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 67131005[2-(4-Chloro-phenyl)-2H-indazol-3-yl]-cyclohexyl-acetic acid

Product 1

HCID 67131197HCID 67131197, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-tetrahydrofuran complex (680 ul, 680 umol; 1 M solution in THF) was added to an ice cold solution of [rac]-[2-(4-chloro-phenyl)-2H-indazol-3-yl]-cyclohexyl-acetic acid (100 mg, 270 umol; example 4.5) in THF (1 ml). The solution was stirred at ambient temperature for 14 h. The solvent was removed under reduced pressure and the residue purified by preparative thin layer chromatography (silica gel, iPrOAc/heptane) to obtain the title compound (56 mg, 160 umol; 58%) as colorless foam. MS: m/e=355.3 [M+H+].

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue purified by preparative thin layer chromatography (silica gel, iPrOAc/heptane)

Sources & evidence

ORD record
ord-22224503165f480ba77b8c9a5f84e2c5
Source dataset
uspto-grants-2011_08
Patent number
US08008505B2

Reaction notes

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