Acrylonitrile → 3-[4-[1-(4-Fluorophenyl)-5-(2-methyltetrazol-5-yl)-1H-indol-3-yl]-1,2,3,6-tetrahydropyridin-1-yl]propionitril

HRID 394589Notes

Reaction equation

HRID 394589 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]4[N:18]=[N:19][N:20]([CH3:22])[N:21]=4)=[CH:14][CH:15]=3)[C:10]([C:23]3[CH2:24][CH2:25][NH:26][CH2:27][CH:28]=3)=[CH:9]2)=[CH:4][CH:3]=1.[C:29](#[N:32])[CH:30]=[CH2:31]>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]4[N:18]=[N:19][N:20]([CH3:22])[N:21]=4)=[CH:14][CH:15]=3)[C:10]([C:23]3[CH2:24][CH2:25][N:26]([CH2:31][CH2:30][C:29]#[N:32])[CH2:27][CH:28]=3)=[CH:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 181772261-(4-fluorophenyl)-5-(2-methyl-5-tetrazolyl)-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole

Product 1

HCID 181772163-[4-[1-(4-Fluorophenyl)-5-(2-methyltetrazol-5-yl)-1H-indol-3-yl]-1,2,3,6-tetrahydropyridin-1-yl]propionitril

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-fluorophenyl)-5-(2-methyl-5-tetrazolyl)-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (21a), (10.2 g) in dichloromethane (100 mL) was added acrylonitril (7.5 g). The mixture was stirred at room temperature for 16 hours. After evaporation of the solvent, the crude title compound 15a remained as a viscous oil which was used without further purification. Yield 12 g.

Workup

  1. customAfter evaporation of the solvent
  2. customwas used without further purification

Sources & evidence

ORD record
ord-f1a190b8ea6c4481a328c1d6272e3b4b
Source dataset
uspto-grants-2003_08
Patent number
US06602889B1

Reaction notes

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