Sodium ethoxide → HCID 58118486, compound

HRID 1182838Notes

Reaction equation

HRID 1182838 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[C:11](Cl)=[N:12][C:13]([Cl:15])=[N:14][C:5]=3[C:4]=2[CH:3]=1.[CH3:17][CH2:18][O-:19].[Na+]>C(O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[C:11]([O:19][CH2:18][CH3:17])=[N:12][C:13]([Cl:15])=[N:14][C:5]=3[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 58118490HCID 58118490, compound

Product 1

HCID 58118486HCID 58118486, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

930 mg (2.9 mmol) 8-bromo-2,4-dichloro-5H-pyrimido[5,4-b]indole was suspended in 20 ml ethanol and mixed with 592 mg (8.7 mmol) sodium ethylate. The mixture was refluxed for 8 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. 920 mg (97%) 8-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 8 h
  2. concentrationthe solvent was concentrated
  3. additionwater was added
  4. washwashed with water

Sources & evidence

ORD record
ord-3d0d5df115dc4ee7baa4892b54d6cd57
Source dataset
uspto-grants-2014_03
Patent number
US08664233B2

Reaction notes

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