Triethylamine → HCID 67973483, compound

HRID 925303Notes

Reaction equation

HRID 925303 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][C:26]([C:27](Cl)=[O:28])=[CH:25][CH:24]=1>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:27](=[O:28])[C:26]1[CH:30]=[CH:31][C:23]([I:22])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 743734-Iodobenzoyl chlorideHCID 28274945-Chloro-1H-indole-3-ethylamine monohydrochloride

Product 1

HCID 67973483HCID 67973483, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(2-(5-chloro-1H-indol-3-yl)ethyl)-4-iodobenzamide was prepared according to method C with triethylamine (2.23 mL; 15.90 mmol), 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (1.5 g; 6.36 mmol) and 4-iodobenzoyl chloride (1.82 g; 6.68 mmol) in dichloromethane (75 mL). The mixture was stirred for 20 minutes at room temperature and was evaporated under reduced pressure. The crude material was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in dichloromethane) to provide 1.22 g (45%) of N-(2-(5-chloro-1H-indol-3-yl)ethyl)-4-iodobenzamide as a white solid.

Workup

  1. customN-(2-(5-chloro-1H-indol-3-yl)ethyl)-4-iodobenzamide was prepared
  2. customwas evaporated under reduced pressure
  3. customThe crude material was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-8f064a51dbf748e799231cf56ec51dd6
Source dataset
uspto-grants-2016_03
Patent number
US09284271B2

Reaction notes

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