Dichloromethane → 4-({2-[2-(2-Amino-ethyl)-1-benzhydryl-5-chloro-1H-indol-3-yl]-ethyl}methyl-amino)-benzoic acid methyl ester

HRID 988908Notes

Reaction equation

HRID 988908 reaction equation
[CH3:1][O:2][C:3](=[O:42])[C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH2:12][CH2:13][C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([Cl:23])[CH:21]=3)[N:16]([CH:24]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:15]=2[CH2:37][CH2:38][N:39]=[N+]=[N-])[CH3:11])=[CH:6][CH:5]=1.C(Cl)Cl>CO.[Pd]>[CH3:1][O:2][C:3](=[O:42])[C:4]1[CH:5]=[CH:6][C:7]([N:10]([CH2:12][CH2:13][C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([Cl:23])[CH:21]=3)[N:16]([CH:24]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:15]=2[CH2:37][CH2:38][NH2:39])[CH3:11])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 865889124-({2-[2-(2-azido-ethyl)-1-benzhydryl-5-chloro-1H-indol-3-yl]-ethyl}methyl-amino)-benzoic acid methyl ester

Product 1

HCID 205985254-({2-[2-(2-Amino-ethyl)-1-benzhydryl-5-chloro-1H-indol-3-yl]-ethyl}methyl-amino)-benzoic acid methyl esterYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-({2-[2-(2-azido-ethyl)-1-benzhydryl-5-chloro-1H-indol-3-yl]-ethyl}-methyl-amino)-benzoic acid methyl ester (410 mg, 0.709 mmol) and 10% Pd/C (155 mg) in MeOH:CH2Cl2 (=7 mL:1 mL) was stirred under H2 atmosphere (1 atm) for 2 h 15 min. The reaction mixture was filtered through celite and rinsed with MeOH and CH2Cl2. Flash column chromatography (CH2Cl2 to 8% MeOH/CH2Cl2) of the residue gave the desired 4-({2-[2-(2-Amino-ethyl)-1-benzhydryl-5-chloro-1H-indol-3-yl]-ethyl}methyl-amino)-benzoic acid methyl ester in 78% yield (305 mg).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washrinsed with MeOH and CH2Cl2

Sources & evidence

ORD record
ord-14c858714b7f49cc89f714b4317d284f
Source dataset
uspto-grants-2003_10
Patent number
US06635771B2

Reaction notes

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