5-Bromopentanenitrile → 3-(4-Cyanobutyl)-2-(3-pyridyl)indole

HRID 1980869Notes

Reaction equation

HRID 1980869 reaction equation
C([Mg]Br)C.[N:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[NH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:6]=1.Br[CH2:21][CH2:22][CH2:23][CH2:24][C:25]#[N:26]>O1CCCC1>[C:25]([CH2:24][CH2:23][CH2:22][CH2:21][C:19]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][C:11]=1[C:7]1[CH:6]=[N:5][CH:10]=[CH:9][CH:8]=1)#[N:26]

Participants

5

Reactant 3

HCID 794355-BromopentanenitrileHCID 6066772-(pyridin-3-yl)-1H-indoleHCID 178418443HCID 178418443, compound

Product 1

HCID 204007973-(4-Cyanobutyl)-2-(3-pyridyl)indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To 6.0 ml of a 2M solution of ethylmagnesium bromide in tetrahydrofuran under nitrogen at 0° is added dropwise over 20 minutes a solution of 2-(3-pyridyl)indole (1.9 g) in 12 ml of tetrahydrofuran. The mixture is stirred at 0° for 0.5 hour and is then treated with a solution of 1.78 g of 5-bromovaleronitrile in 4 ml of tetrahydrofuran. This mixture is stirred at 0° for 1 hour, then at room temperature for 1 hour, and is then poured into 125 ml of ice-water. This is extracted with 2×50 ml of ether, the extract is washed with water, dried, evaporated to dryness and purified to give 3-(4-cyanobutyl)-2-(3-pyridyl)indole.

Workup

  1. stirringThis mixture is stirred at 0° for 1 hour
  2. waitat room temperature for 1 hour
  3. extractionThis is extracted with 2×50 ml of ether
  4. washthe extract is washed with water
  5. customdried
  6. customevaporated to dryness
  7. custompurified

Sources & evidence

ORD record
ord-3baa466213b94353946d4f8664bb3ad7
Source dataset
uspto-grants-1985_04
Patent number
US04511573

Reaction notes

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