HCID 68701411, compound → HCID 68696976, compound

HRID 646099Notes

Reaction equation

HRID 646099 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH:35]([CH3:37])[CH3:36])=[CH:30][CH:29]=2)[C:8]2[C:13]([CH:14]=1)=[C:12]([N+:15]([O-])=O)[C:11]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH:25]([CH3:27])[CH3:26])=[CH:20][CH:19]=1)=[CH:10][CH:9]=2)=[O:5])[CH3:2]>CCOC(C)=O.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[N:7]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH:35]([CH3:36])[CH3:37])=[CH:30][CH:29]=2)[C:8]2[C:13]([CH:14]=1)=[C:12]([NH2:15])[C:11]([C:18]1[CH:19]=[CH:20][C:21]([O:24][CH:25]([CH3:27])[CH3:26])=[CH:22][CH:23]=1)=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 68701411HCID 68701411, compound

Product 1

HCID 68696976HCID 68696976, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A stirred mixture of 1,5-bis(4-isopropoxyphenyl)-4-nitroindole-2-carboxylic acid ethyl ester (335 mg, 0.67 mmol; see Example 4(b)) and Pd/C (10%, 120 mg) in EtOAc was hydrogenated at ambient pressure and temperature for 10 h and filtered through Celite®. The filter cake was washed with EtOAc and the combined filtrates were concentrated and purified by chromatography to yield the sub-title compound (272 mg, 86%).

Workup

  1. filtrationfiltered through Celite®
  2. washThe filter cake was washed with EtOAc
  3. concentrationthe combined filtrates were concentrated
  4. custompurified by chromatography

Sources & evidence

ORD record
ord-bcf0f74bf2d04572b5e34de0a5e3c2d4
Source dataset
uspto-grants-2010_04
Patent number
US07705023B2

Reaction notes

Loading…