Water → 3-Chloro-N-[1-(2-chlorophenyl)-2-[1-(2-fluoroethyl)-piperidin-4-ylmethoxy]ethyl]-1H-indole-6-carboxamide

HRID 32426

Reaction equation

HRID 32426 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([NH:13][CH:14]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])[CH2:15][O:16][CH2:17][CH:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[O:12])=[CH:8][CH:9]=2)[NH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:38][CH2:39][F:40].O>CS(C)=O>[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([NH:13][CH:14]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])[CH2:15][O:16][CH2:17][CH:18]3[CH2:23][CH2:22][N:21]([CH2:38][CH2:39][F:40])[CH2:20][CH2:19]3)=[O:12])=[CH:8][CH:9]=2)[NH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 129822-Fluoroethyl bromideHCID 693078883-chloro-N-[1-(2-chlorophenyl)-2-(piperidin-4-ylmethoxy)ethyl]-1H-indole-6-carboxamide

Product 1

HCID 866036003-Chloro-N-[1-(2-chlorophenyl)-2-[1-(2-fluoroethyl)-piperidin-4-ylmethoxy]ethyl]-1H-indole-6-carboxamideYield 32.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 3-chloro-N-[1-(2-chlorophenyl)-2-(piperidin-4-ylmethoxy)ethyl]-1H-indole-6-carboxamide (600 mg, 1.3 mmol) in 6 mL of DMSO was added potassium carbonate (716 mg, 5.2 mmol) and 2-bromo-1-fluoroethane (0.10 mL, 1.1 mmol). The reaction was allowed to stir at room temperature overnight after which time water was added and the resulting precipitate was isolated by filtration. Purification of the filtrate (SiO2: EtOAc) provided 178 mg (28%) of the title compound.

Workup

  1. additionwas added
  2. customthe resulting precipitate was isolated by filtration
  3. customPurification of the filtrate (SiO2: EtOAc)

Sources & evidence

ORD record
ord-e49489d5264c4cecbfe01b7713b6f1d6
Source dataset
uspto-grants-2008_09
Patent number
US07427632B2

Linked notes

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