Imidazole → HCID 67974070, compound

HRID 1777594Notes

Reaction equation

HRID 1777594 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][C:18]([CH2:21]Cl)=[CH:17][CH:16]=1.[NH:24]1[CH:28]=[CH:27][N:26]=[CH:25]1.[I-].[Na+]>C1COCC1>[N:24]1([CH2:21][C:18]2[CH:19]=[CH:20][C:15]([C:14]([NH:13][CH2:12][CH2:11][C:5]3[C:4]4[C:8](=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=4)[NH:7][CH:6]=3)=[O:23])=[CH:16][CH:17]=2)[CH:28]=[CH:27][N:26]=[CH:25]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 5238Sodium IodideHCID 67974260HCID 67974260, compound

Product 1

HCID 67974070HCID 67974070, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-((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)-4-(chloromethyl)benzamide (0.070 g; 0.202 mmol), imidazole (0.062 g; 0.907 mmol) and sodium iodide (0.152 g; 1.01 mmol) in THF (3 mL), under a microwave irradiation at 150° C. for 20 minutes. Flash chromatography on silica gel (eluent 3 to 20% ethanol in dichloromethane) furnished 0.021 g (41%) of the title compound as a white solid.

Workup

  1. custom4-((1H-Imidazol-1-yl)methyl)-N-(2-(5-chloro-1H-indol-3-yl)ethyl)benzamide was prepared

Sources & evidence

ORD record
ord-6f1dc9e7eaad46608e886ecc84d910f0
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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