Triethylamine → Ethyl 3-[({2-[(tert-butoxycarbonyl)amino]ethyl}amino)sulfonyl]-5-iodo-1-(phenylsulfonyl)-1H-indole-2-carboxylate

HRID 1676999Notes

Reaction equation

HRID 1676999 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:13])=[O:12])[C:6]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:5]2[S:25](Cl)(=[O:27])=[O:26].[C:29]([NH:36][CH2:37][CH2:38][NH2:39])([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30].C(N(CC)CC)C>ClCCl.CCOC(C)=O>[C:32]([O:31][C:29]([NH:36][CH2:37][CH2:38][NH:39][S:25]([C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([I:1])[CH:3]=2)[N:7]([S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])[C:6]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21])(=[O:27])=[O:26])=[O:30])([CH3:35])([CH3:34])[CH3:33]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 187201N-BOC-ethylenediamineHCID 86601816ethyl 5-iodo-3-(chlorosulfonyl)-1-(phenylsulfonyl)-1H-indole-2-carboxylate

Product 1

HCID 67375255Ethyl 3-[({2-[(tert-butoxycarbonyl)amino]ethyl}amino)sulfonyl]-5-iodo-1-(phenylsulfonyl)-1H-indole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product from Example 4 Step C (235 mg) was combined with Boc-ethylenediamine (74 μL) and triethylamine (178 μL) in 3 mL of dichloromethane and stirred at room temperature for 1 hour. The reaction was diluted with EtOAc and washed with saturated NaHCO3 and brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel using EtOAc/hexane as mobile phase to give the titled compound. ESI+ MS: 678 [M+H]+.

Workup

  1. washwashed with saturated NaHCO3 and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-a40fc2bbbe1b484e9d67af870a9a8e4f
Source dataset
uspto-grants-2011_08
Patent number
US08008295B2

Reaction notes

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