Sodium Iodide → N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-((ethylamino)methyl)isoxazole-3-carboxamide

HRID 58689Notes

Reaction equation

HRID 58689 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][NH:13][C:14]([C:16]1[CH:20]=[C:19]([CH2:21]Cl)[O:18][N:17]=1)=[O:15].[Na+].[I-].[CH2:25]([NH2:27])[CH3:26]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][NH:13][C:14]([C:16]1[CH:20]=[C:19]([CH2:21][NH:27][CH2:25][CH3:26])[O:18][N:17]=1)=[O:15]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6341EthylamineHCID 66831699N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-(chloromethyl)isoxazole-3-carboxamide

Product 1

HCID 66831786N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-((ethylamino)methyl)isoxazole-3-carboxamideYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the intermediate 7: N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-(chloromethyl)isoxazole-3-carboxamide (0.088 g; 0.260 mmol) NaI (0.078 g; 0.520 mmol) and ethylamine (1.30 mL; 2M in THF) in THF (1 mL) was irradiated in a microwave oven at 130° C. for 10 min and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluent 2 to 10% MeOH in dichloromethane) to afford N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-((ethylamino)methyl)isoxazole-3-carboxamide 0.044 g (50%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude material was purified by flash chromatography (eluent 2 to 10% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-fd220d36a6294a54ab3e9da11b842bcb
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

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