Methyl iodide → 1-((3-(3,4-Difluorobenzylcarbamoyl)-6-isopropoxy-1-(pyridin-2-ylmethyl)-1H-indol-2-yl)methyl)-1-methylpyrrolidinium iodide

HRID 40148Notes

Reaction equation

HRID 40148 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:35]=[CH:36][C:37]=1[F:38])[CH2:5][NH:6][C:7]([C:9]1[C:17]2[C:12](=[CH:13][C:14]([O:18][CH:19]([CH3:21])[CH3:20])=[CH:15][CH:16]=2)[N:11]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[C:10]=1[CH2:29][N:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1)=[O:8].[CH3:39][I:40]>CC(C)=O>[I-:40].[F:1][C:2]1[CH:3]=[C:4]([CH:35]=[CH:36][C:37]=1[F:38])[CH2:5][NH:6][C:7]([C:9]1[C:17]2[C:12](=[CH:13][C:14]([O:18][CH:19]([CH3:21])[CH3:20])=[CH:15][CH:16]=2)[N:11]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[C:10]=1[CH2:29][N+:30]1([CH3:39])[CH2:31][CH2:32][CH2:33][CH2:34]1)=[O:8]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 59762441N-(3,4-difluorobenzyl)-6-isopropoxy-1-(pyridin-2-ylmethyl)-2-(pyrrolidin-1-ylmethyl)-1H-indole-3-carboxamide2×

Product 1

HCID 718111441-((3-(3,4-Difluorobenzylcarbamoyl)-6-isopropoxy-1-(pyridin-2-ylmethyl)-1H-indol-2-yl)methyl)-1-methylpyrrolidinium iodide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of N-(3,4-difluorobenzyl)-6-isopropoxy-1-(pyridin-2-ylmethyl)-2-(pyrrolidin-1-ylmethyl)-1H-indole-3-carboxamide (Compound 175, 17 mg, 0.033 mmol) in acetone (1 ml) was added MeI (0.1 ml, 1.6 mmol). The reaction was stirred at room temperature for 16 h and the solvent was removed in vacuo. The residue was purified by PTLC on silica gel (10% MeOH-EtOAc) to yield the title compound.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was purified by PTLC on silica gel (10% MeOH-EtOAc)

Sources & evidence

ORD record
ord-41592bfed55d498ca6eccf0cd2b1560d
Source dataset
uspto-grants-2013_09
Patent number
US08524917B2

Reaction notes

Loading…