Sodium ethoxide → HCID 58118559, compound

HRID 1182852Notes

Reaction equation

HRID 1182852 reaction equation
[Br:1][C:2]1[C:10]2[NH:9][C:8]3[C:11](Cl)=[N:12][C:13]([Cl:15])=[N:14][C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:17][CH2:18][O-:19].[Na+]>C(O)C>[Br:1][C:2]1[C:10]2[NH:9][C:8]3[C:11]([O:19][CH2:18][CH3:17])=[N:12][C:13]([Cl:15])=[N:14][C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 58118520HCID 58118520, compound

Product 1

HCID 58118559HCID 58118559, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.0 g (3.2 mmol) 6-bromo-2,4-dichloro-5H-pyrimido[5,4-b]indole was suspended in 5 ml absolute ethanol and mixed with 6 ml (6.4 mmol) 1M sodium ethylate solution (EtOH). The mixture was refluxed for 15 h. Having cooled down to room temperature, the solvent was concentrated and water was added. The resulting precipitate was sucked off and washed with water. 0.9 g (86%) 6-bromo-2-chloro-4-ethoxy-5H-pyrimido[5,4-b]indole was obtained. ESI-MS [m/z]: 324, 326 [M−H]−

Workup

  1. temperatureThe mixture was refluxed for 15 h
  2. concentrationthe solvent was concentrated
  3. additionwater was added
  4. washwashed with water

Sources & evidence

ORD record
ord-b3f47d33ed15418f8a83e6684540f052
Source dataset
uspto-grants-2014_03
Patent number
US08664233B2

Reaction notes

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