Sodium hydride → HCID 67309163, compound

HRID 1877439Notes

Reaction equation

HRID 1877439 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]([C:7]1[C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][C:11]=2[CH:10]=[CH:9][CH:8]=1)=[O:6].[Br:20][C:21]1[CH:28]=[C:27](F)[CH:26]=[CH:25][C:22]=1[C:23]#[N:24]>CN(C)C=O>[CH3:3][O:4][C:5]([C:7]1[C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([C:27]3[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([Br:20])[CH:28]=3)[C:11]=2[CH:10]=[CH:9][CH:8]=1)=[O:6]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1189392-Bromo-4-fluorobenzonitrileHCID 19897888Methyl 9H-carbazole-4-carboxylate

Product 1

HCID 67309163HCID 67309163, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 250 ml round-bottomed flask under argon, 391 mg of a suspension of sodium hydride at 60% in petroleum jelly are added at ambient temperature, in 4 stages, in ½ hour, to a solution of 2.0 g of 9H-carbazole-4-carboxylic acid methyl ester obtained according to the preceding stage and of 1.95 g of 2-bromo-4-fluorobenzonitrile in 50 ml of dimethylformamide. The mixture is stirred at ambient temperature for 3 hours. The reaction medium is evaporated to dryness under vacuum and the residue is chromatographed on silica gel (40-63 μm), elution being carried out with a mixture of dichloromethane and cyclohexane (50:50). 3.2 g of 9-(3-bromo-4-cyanophenyl)-9H-carbazole-4-carboxylic acid methyl ester are obtained in the form of a white solid, the characteristics of which are the following:

Workup

  1. customobtained
  2. customThe reaction medium is evaporated to dryness under vacuum
  3. customthe residue is chromatographed on silica gel (40-63 μm), elution
  4. additionbeing carried out with a mixture of dichloromethane and cyclohexane (50:50)

Sources & evidence

ORD record
ord-e2c8c858cb4043f29d79fcd523b7b421
Source dataset
uspto-grants-2012_11
Patent number
US08309721B2

Reaction notes

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