Cyclohexene → HCID 66657709, compound

HRID 420998Notes

Reaction equation

HRID 420998 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([C:32]2[CH:37]=[CH:36][C:35]([O:38][CH:39]([CH3:41])[CH3:40])=[CH:34][CH:33]=2)[C:8]2[C:13]([C:14]=1[CH:15]=[CH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:12][C:11]([C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][N:23]=1)=[CH:10][CH:9]=2)=[O:5])[CH3:2].C1CCCCC=1>CCO.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[N:7]([C:32]2[CH:37]=[CH:36][C:35]([O:38][CH:39]([CH3:41])[CH3:40])=[CH:34][CH:33]=2)[C:8]2[C:13]([C:14]=1[CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:12][C:11]([C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:30])([F:29])[F:31])=[CH:24][N:23]=1)=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 66657620HCID 66657620, compound

Product 1

HCID 66657709HCID 66657709, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 3-(2-ethoxycarbonylvinyl)-1-(4-isopropoxyphenyl)-5-(5-trifluoromethylpyridin-2-yl)indole-2-carboxylic acid ethyl ester (150 mg, 0.26 mmol, see step (c) above), Pd—C (10%), cyclohexene (1.2 mL) in absolute EtOH was heated under microwave irradiation at 135° C. for 1 h. The mixture was filtered through Celite® and the solids were washed with EtOAc. The combined filtrates were concentrated to give the sub-title compound. Yield 150 mg (100%).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. washthe solids were washed with EtOAc
  3. concentrationThe combined filtrates were concentrated

Sources & evidence

ORD record
ord-2d872bc0bca746c39f1eab39fc16c530
Source dataset
uspto-grants-2012_01
Patent number
US08097623B2

Reaction notes

Loading…