Triethylamine → N-(2-(5-chloro-1H-indol-3-yl)ethyl)-2-iodobenzamide

HRID 925301Notes

Reaction equation

HRID 925301 reaction equation
C(N(CC)CC)C.Cl.[Cl:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[C:13]2[CH2:19][CH2:20][NH2:21].[I:22][C:23]1[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=1[C:25](Cl)=[O:26]>ClCCl>[Cl:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[C:13]2[CH2:19][CH2:20][NH:21][C:25](=[O:26])[C:24]1[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=1[I:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 691122-Iodobenzoyl chlorideHCID 28274945-Chloro-1H-indole-3-ethylamine monohydrochloride

Product 1

HCID 17271791N-(2-(5-chloro-1H-indol-3-yl)ethyl)-2-iodobenzamideYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(2-(5-chloro-1H-indol-3-yl)ethyl)-2-iodobenzamide was prepared according to method C with triethylamine (1.19 mL; 8.48 mmol), 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.800 g; 3.90 mmol) and 2-iodobenzoyl chloride (0.968 g; 3.56 mmol) in dichloromethane (75 mL). The mixture was stirred for 20 minutes at room temperature and was evaporated to dryness. The crude material was purified by flash chromatography on silica gel (eluent 1 to 10% ethyl acetate in dichloromethane) to furnish 1.32 g (92%) of N-(2-(5-chloro-1H-indol-3-yl)ethyl)-2-iodobenzamide as a white solid.

Workup

  1. customN-(2-(5-chloro-1H-indol-3-yl)ethyl)-2-iodobenzamide was prepared
  2. customwas evaporated to dryness
  3. customThe crude material was purified by flash chromatography on silica gel (eluent 1 to 10% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-def96b2045494b1b94d3a75d870fd852
Source dataset
uspto-grants-2016_03
Patent number
US09284271B2

Reaction notes

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