Benzene, 1-chloro-4-fluoro- → HCID 21195967, compound

HRID 1066791Notes

Reaction equation

HRID 1066791 reaction equation
[OH:1][CH2:2][C:3]1[N:4]([CH2:12][CH2:13][CH2:14][CH:15]2[CH2:20][CH2:19][CH2:18][N:17]([C:21]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:16]2)[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[H-].[Na+].[Cl:42][C:43]1[CH:48]=[CH:47][C:46](F)=[CH:45][CH:44]=1>CN(C)C=O>[Cl:42][C:43]1[CH:48]=[CH:47][C:46]([O:1][CH2:2][C:3]2[N:4]([CH2:12][CH2:13][CH2:14][CH:15]3[CH2:20][CH2:19][CH2:18][N:17]([C:21]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:16]3)[C:5]3[C:10]([CH:11]=2)=[CH:9][CH:8]=[CH:7][CH:6]=3)=[CH:45][CH:44]=1

Participants

5

Reactant 3

HCID 9604Benzene, 1-chloro-4-fluoro-2×HCID 24758Sodium hydride2×HCID 21195972HCID 21195972, compound

Product 1

HCID 21195967HCID 21195967, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under an argon atmosphere 2-hydroxymethyl-1-[3-(1-tritylpiperidin-3-yl)propyl]-1H-indole (2.89 g, 5,61 mmol) was dissolved in about 11.2 ml of N,N-dimethylformamide. The resulting solution was then placed in an ice bath and sodium hydride (0.247 g of a 60% suspension in mineral oil, 6.18 mmol) was added and the resulting mixture was stirred at room temperature for about 60 minutes. To the reaction mixture 1-chloro-4-fluorobenzene (0.658 ml, 0.807 g, 6.18 mmol) was added and the resulting mixture was stirred at room temperature overnight. The reaction mixture was then heated to 80° C. and maintained at this temperature for about eight hours. The reaction mixture was then cooled to room temperature and stirred at this temperature overnight. Another half equivalence of sodium hydride was added and the reaction mixture was stirred at room temperature overnight again. Another half equivalence of 1-chloro-4-fluorobenzene was added and the reaction mixture was heated to 80° C.

Workup

  1. customThe resulting solution was then placed in an ice bath
  2. stirringthe resulting mixture was stirred at room temperature overnight
  3. temperatureThe reaction mixture was then heated to 80° C.
  4. temperaturemaintained at this temperature for about eight hours
  5. temperatureThe reaction mixture was then cooled to room temperature
  6. stirringstirred at this temperature overnight
  7. stirringthe reaction mixture was stirred at room temperature overnight again
  8. temperaturethe reaction mixture was heated to 80° C.

Sources & evidence

ORD record
ord-c8fcb9b8c0994ca98f4faa69786b1340
Source dataset
uspto-grants-2001_06
Patent number
US06245761B1

Reaction notes

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