1,3-Dibromopropane → 1-(3'-Bromopropyl)-5-cyano-3-phenylindazole

HRID 1649079Notes

Reaction equation

HRID 1649079 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][N:7]=[C:6]2[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)#[N:2].[H-].[Na+].[Br:20][CH2:21][CH2:22][CH2:23]Br>CN(C)C=O>[Br:20][CH2:21][CH2:22][CH2:23][N:8]1[C:9]2[C:5](=[CH:4][C:3]([C:1]#[N:2])=[CH:11][CH:10]=2)[C:6]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[N:7]1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 130669563-Phenyl-1H-5-indazolecarbonitrile

Product 1

HCID 130669571-(3'-Bromopropyl)-5-cyano-3-phenylindazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 4.2 g of the 5-cyano-3-phenylindazole in 20 ml of dimethylformamide, 0.8 g of 60% sodium hydride was added, and the mixture was stirred for 10 minutes. The mixture was added dropwise to a mixture of 7 ml of 1,3-dibromopropane and 10 ml of dimethylformamide under cooling with ice. The mixture was stirred for 10 minutes at room temperature and extracted with benzene. The extract was washed with water, dried over anhydrous sodium sulfate and concentrated. The residue was subjected to column chromatography on silica gel to produce 3.5 g of 1-(3'-bromopropyl)-5-cyano-3-phenylindazole (recrystallization from ethanol provided a m.p. of 100° to 102° C.).

Workup

  1. temperatureunder cooling with ice
  2. stirringThe mixture was stirred for 10 minutes at room temperature
  3. extractionextracted with benzene
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e2ab7fa37fde4270af7ce1b9c4d40436
Source dataset
uspto-grants-1983_11
Patent number
US04415569

Reaction notes

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