Sodium hydride → 3-Bromo-8H-8,12b-diazabenzo[a]aceanthrylene

HRID 1485588Notes

Reaction equation

HRID 1485588 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH2:21])[C:10]1[C:9](F)=[CH:8][CH:7]=[CH:6][C:5]2=1.[H-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[N:11]3[C:10]4[C:5]([C:4]=2[CH:3]=1)=[CH:6][CH:7]=[CH:8][C:9]=4[NH:21][C:16]1[C:15]3=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 673251662-(6-Bromo-1-fluorocarbazol-9-yl)phenylamine

Product 1

HCID 673253603-Bromo-8H-8,12b-diazabenzo[a]aceanthrylene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under a protective gas, 25 g (72 mmol) of 2-(6-bromo-1-fluorocarbazol-9-yl)phenylamine are dissolved in 200 ml of DMF, 2.8 g (72 mmol) of NaH (60% in oil) are added at room temperature, and the mixture is heated under reflux for 6 h. The mixture is allowed to come to room temperature over the course of 1 h, the solvent is then removed, and the residue is purified by chromatography. The yield is 19 g (54 mmol), corresponding to 78% of theory.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 6 h
  3. customto come to room temperature over the course of 1 h
  4. customthe solvent is then removed
  5. customthe residue is purified by chromatography

Sources & evidence

ORD record
ord-59a5d6c4ffb5497c8f69223968fbd4fa
Source dataset
uspto-grants-2016_08
Patent number
US09422287B2

Reaction notes

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