N-(2-(1H-indol-3-yl)ethyl)-2-(tert-butyldimethylsilyloxy)ethanamine → (E)-3-{1-[4-({[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-[2-(1H-indol-3-yl)-ethyl]-amino}-methyl)-benzenesulfonyl]-1H-pyrrol-3-yl}-acrylic acid tert-butyl ester

HRID 870099Notes

Reaction equation

HRID 870099 reaction equation
[C:1]([Si:5]([CH3:22])([CH3:21])[O:6][CH2:7][CH2:8][NH:9][CH2:10][CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[C:23]([O:27][C:28](=[O:47])/[CH:29]=[CH:30]/[C:31]1[CH:35]=[CH:34][N:33]([S:36]([C:39]2[CH:44]=[CH:43][C:42]([CH2:45]Br)=[CH:41][CH:40]=2)(=[O:38])=[O:37])[CH:32]=1)([CH3:26])([CH3:25])[CH3:24]>C(O)C>[C:23]([O:27][C:28](=[O:47])/[CH:29]=[CH:30]/[C:31]1[CH:35]=[CH:34][N:33]([S:36]([C:39]2[CH:44]=[CH:43][C:42]([CH2:45][N:9]([CH2:8][CH2:7][O:6][Si:5]([C:1]([CH3:2])([CH3:4])[CH3:3])([CH3:22])[CH3:21])[CH2:10][CH2:11][C:12]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[NH:14][CH:13]=3)=[CH:41][CH:40]=2)(=[O:38])=[O:37])[CH:32]=1)([CH3:26])([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 58756770N-(2-(1H-indol-3-yl)ethyl)-2-(tert-butyldimethylsilyloxy)ethanamine2×HCID 66646385(E)-3-[1-(4-bromomethyl-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylic acid tert-butyl ester2×

Product 1

HCID 66646255(E)-3-{1-[4-({[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-[2-(1H-indol-3-yl)-ethyl]-amino}-methyl)-benzenesulfonyl]-1H-pyrrol-3-yl}-acrylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-[2-(1H-Indol-3yl)-ethyl]-amine (compound E2) (830 mg, 2.60 mmol) is dissolved in ethanol (200 ml). (E)-3-[1-(4-bromomethyl-benzenesulfonyl)-1H-pyrrol-3yl]-acrylic acid tert-butyl ester (compound D4) (1.01 g, 2.37 mmol) is added and the mixture is stirred for 43 hours and evaporated. The residue is purified by a silica gel flash chromatograph using petrol ether-ether eluent.

Workup

  1. customevaporated
  2. customThe residue is purified by a silica gel flash chromatograph

Sources & evidence

ORD record
ord-fc2691b3e1e1402b92c01a9091f65824
Source dataset
uspto-grants-2015_03
Patent number
US08969401B2

Reaction notes

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