2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → [2-(4-Chloro-phenyl)-2H-indazol-3-yl]-cyclohexyl-acetic acid ethyl ester

HRID 1678618Notes

Reaction equation

HRID 1678618 reaction equation
ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.[CH2:15]([O:17][C:18](=[O:42])[CH:19]([C:26]1[N:27]([C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=2)[N:28]=[C:29]2[C:34]=1[CH2:33][CH2:32][CH2:31][CH2:30]2)[CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[CH3:16]>O1CCOCC1>[CH2:15]([O:17][C:18](=[O:42])[CH:19]([C:26]1[N:27]([C:35]2[CH:36]=[CH:37][C:38]([Cl:41])=[CH:39][CH:40]=2)[N:28]=[C:29]2[C:34]=1[CH:33]=[CH:32][CH:31]=[CH:30]2)[CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[CH3:16]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 67131110[2-(4-Chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-cyclohexyl-acetic acid ethyl ester

Product 1

HCID 67131064[2-(4-Chloro-phenyl)-2H-indazol-3-yl]-cyclohexyl-acetic acid ethyl esterYield 19%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2,3-Dichloro-5,6-dicyanobenzoquinone (136 mg, 600 μmol) was added to a solution of [2-(4-chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-cyclohexyl-acetic acid ethyl ester (60 mg, 150 μmol in dioxane (3.3 ml) under an argon atmosphere. The reaction mixture was heated under reflux conditions for 4 d. The solvent was removed under reduced pressure and the residue was purified by column chromatography (silica gel, iPrOAc/heptane) to give the title compound (11 mg, 28 μmol; 19%) as colorless solid. MS: m/e=397.0 [M+H+].

Workup

  1. temperatureThe reaction mixture was heated under reflux conditions for 4 d
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by column chromatography (silica gel, iPrOAc/heptane)

Sources & evidence

ORD record
ord-8eb98446acc64f3a881037bd74614210
Source dataset
uspto-grants-2011_08
Patent number
US08008505B2

Reaction notes

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