Sodium Iodide → HCID 67974685, compound

HRID 1777610Notes

Reaction equation

HRID 1777610 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.[S:24]1[CH:28]=[CH:27][CH:26]=[C:25]1[CH2:29][NH2:30].[I-].[Na+]>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](=[O:23])[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][NH:30][CH2:29][C:25]2[S:24][CH:28]=[CH:27][CH:26]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 34005(2-Thienylmethyl)amineHCID 67974260HCID 67974260, compound

Product 1

HCID 67974685HCID 67974685, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(2-(5-Chloro-1H-indol-3-yl)ethyl)-4-((thiophen-2-ylmethylamino)methyl)benzamide was prepared following Method C starting from N-(2-(5-chloro-1H-indol-3-yl)ethyl)-4-(chloromethyl)benzamide (0.100 g; 0.288 mmol), thiophen-2-ylmethanamine (0.138 mL; 1.30 mmol) and sodium iodide (0.218 g; 1.44 mmol) in THF (3 mL), under a microwave irradiation at 150° C. for 10 minutes. Flash chromatography on silica gel (eluent 2 to 10% methanol in dichloromethane) furnished 0.086 g (71%) of the title compound as a white solid.

Workup

  1. customN-(2-(5-Chloro-1H-indol-3-yl)ethyl)-4-((thiophen-2-ylmethylamino)methyl)benzamide was prepared

Sources & evidence

ORD record
ord-8da388fab6ff4eff84b4ed84275c1a5b
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

Loading…