Benzene, 1-chloro-4-fluoro- → HCID 21196110, compound

HRID 1066790Notes

Reaction equation

HRID 1066790 reaction equation
[OH:1][CH2:2][C:3]1[N:4]([CH2:12][CH2:13][CH:14]2[CH2:19][CH2:18][N:17]([C:20]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:16][CH2:15]2)[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[H-].[Na+].[Cl:41][C:42]1[CH:47]=[CH:46][C:45](F)=[CH:44][CH:43]=1>CN(C)C=O>[Cl:41][C:42]1[CH:47]=[CH:46][C:45]([O:1][CH2:2][C:3]2[N:4]([CH2:12][CH2:13][CH:14]3[CH2:19][CH2:18][N:17]([C:20]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:16][CH2:15]3)[C:5]3[C:10]([CH:11]=2)=[CH:9][CH:8]=[CH:7][CH:6]=3)=[CH:44][CH:43]=1

Participants

5

Reactant 3

HCID 9604Benzene, 1-chloro-4-fluoro-HCID 24758Sodium hydrideHCID 21195952HCID 21195952, compound

Product 1

HCID 21196110HCID 21196110, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under an argon atmosphere 2-hydroxymethyl-1-[2-(1-tritylpiperidin-4-yl)ethyl]-1H-indole (3.91 g, 7.81 mmol) was dissolved in about 10 ml of N,N-dimethylformamide. The resulting solution was then placed in an ice bath and sodium hydride (0.468 g, 11.71 mmol) was added and the resulting mixture was stirred at room temperature for about 30 minutes. To the reaction mixture 1-chloro-4-fluorobenzene (0.915 ml, 1.12 g, 8.59 mmol) was added and the resulting mixture was stirred at room temperature for about four days, protected from light.

Workup

  1. customThe resulting solution was then placed in an ice bath
  2. stirringthe resulting mixture was stirred at room temperature for about four days

Sources & evidence

ORD record
ord-426d461627cc47a3be3e137c0c270052
Source dataset
uspto-grants-2001_06
Patent number
US06245761B1

Reaction notes

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