Triethylamine → N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-methyl-2-phenylfuran-3-carboxamide

HRID 58779Notes

Reaction equation

HRID 58779 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].[CH3:22][C:23]1[O:27][C:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:25]([C:34](Cl)=[O:35])[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:34]([C:25]1[CH:24]=[C:23]([CH3:22])[O:27][C:26]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28274945-Chloro-1H-indole-3-ethylamine monohydrochlorideHCID 152697375-Methyl-2-phenylfuran-3-carbonyl chloride

Product 1

HCID 66831979N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-methyl-2-phenylfuran-3-carboxamideYield 86.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.128 mL; 0.886 mmol) was added to a mixture of 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.082 g; 0.354 mmol) and 5-methyl-2-phenylfuran-3-carbonyl chloride (0.082 g; 0.372 mmol) in dichloromethane (7 mL) at room temperature. The reaction mixture was stirred at room temperature for 20 minutes and washed with water. The organic layer was concentrated under reduced pressure and the crude material was purified by flash chromatography on silica gel (eluent 2 to 10% ethyl acetate in dichloromethane) to afford 0.116 g (86%) of N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-methyl-2-phenylfuran-3-carboxamide as a solid.

Workup

  1. washwashed with water
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customthe crude material was purified by flash chromatography on silica gel (eluent 2 to 10% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-c2c2dc50117e487abd4b31de5c10600e
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

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