Imidazole → HCID 67974366, compound

HRID 1777595Notes

Reaction equation

HRID 1777595 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](=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21]Cl)[CH:16]=1.[NH:24]1[CH:28]=[CH:27][N:26]=[CH:25]1.[I-].[Na+]>C1COCC1>[N:24]1([CH2:21][C:17]2[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=2)[C:14]([NH:13][CH2:12][CH2:11][C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=3)[NH:7][CH:6]=2)=[O:23])[CH:28]=[CH:27][N:26]=[CH:25]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 5238Sodium IodideHCID 67974165N-(2-(5-chloro-1H-indol-3-yl)ethyl)-3-(chloromethyl)benzamide

Product 1

HCID 67974366HCID 67974366, compoundYield 16.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-((1H-Imidazol-1-yl)methyl)-N-(2-(5-chloro-1H-indol-3-yl)ethyl)benzamide was prepared following Method C starting from N-(2-(5-chloro-1H-indol-3-yl)ethyl)-3-(chloromethyl)benzamide (0.050 g; 0.144 mmol), imidazole (0.034 g; 0.5 mmol) and sodium iodide (0.090 g; 0.6 mmol) in THF (3 mL), under a microwave irradiation at 150° C. for 20 minutes. Flash chromatography on silica gel (eluent 0 to 10% methanol in dichloromethane) furnished 0.009 g (16%) of the title compound as a white solid.

Workup

  1. custom3-((1H-Imidazol-1-yl)methyl)-N-(2-(5-chloro-1H-indol-3-yl)ethyl)benzamide was prepared

Sources & evidence

ORD record
ord-dce58104159a4bb38d43f08414e4974c
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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