5-chloro-1H-indole-7-carboxylic acid [2-(3-benzyloxy-phenyl)-ethyl]-(4-tert-butyl-benzyl)-amide → HCID 86603055, compound

HRID 855351Notes

Reaction equation

HRID 855351 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][N:17]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]([CH3:40])([CH3:39])[CH3:38])=[CH:33][CH:32]=2)[C:18]([C:20]2[CH:21]=[C:22]([Cl:29])[CH:23]=[C:24]3[C:28]=2[NH:27][CH:26]=[CH:25]3)=[O:19])[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>CCOC(C)=O.[Pd]>[C:37]([C:34]1[CH:35]=[CH:36][C:31]([CH2:30][N:17]([CH2:16][CH2:15][C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([OH:8])[CH:10]=2)[C:18]([C:20]2[CH:21]=[C:22]([Cl:29])[CH:23]=[C:24]3[C:28]=2[NH:27][CH:26]=[CH:25]3)=[O:19])=[CH:32][CH:33]=1)([CH3:40])([CH3:38])[CH3:39]

Participants

4

Reactant 1

HCID 866030545-chloro-1H-indole-7-carboxylic acid [2-(3-benzyloxy-phenyl)-ethyl]-(4-tert-butyl-benzyl)-amide

Product 1

HCID 86603055HCID 86603055, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

200 mg of 5-chloro-1H-indole-7-carboxylic acid [2-(3-benzyloxy-phenyl)-ethyl]-(4-tert-butyl-benzyl)-amide (0.36 mmol) were dissolved in 20 ml EtOAc and hydrogenated for 5 h over 20 mg Pd/C 10%. After removal of the catalyst by filtration, the solution was concentrated in vacuo and the residue purified by column chromatography (8 g silicagel, heptane/EtOAc 2:1) leading to 136 mg of 5-chloro-1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(3-hydroxy-phenyl)-ethyl]-amide (79%) as a light yellow solid. MS (ISP) 461.4 (M+H)+.

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. concentrationthe solution was concentrated in vacuo
  4. customthe residue purified by column chromatography (8 g silicagel, heptane/EtOAc 2:1)

Sources & evidence

ORD record
ord-734725bfc473403996be7fe780f9daad
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

Loading…