Sodium ethoxide → 7-bromo-2-chloro-4-ethoxy-5H-pyrimido[5,4-b]indole

HRID 1182842Notes

Reaction equation

HRID 1182842 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]=[C:13]([Cl:15])[N:12]=[C:11](Cl)[C:7]=3[NH:8][C:9]=2[CH:10]=1.[CH3:17][CH2:18][O-:19].[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]=[C:13]([Cl:15])[N:12]=[C:11]([O:19][CH2:18][CH3:17])[C:7]=3[NH:8][C:9]=2[CH:10]=1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 581184877-bromo-2,4-dichloro-5H-pyrimido[5,4-b]indole

Product 1

HCID 581185367-bromo-2-chloro-4-ethoxy-5H-pyrimido[5,4-b]indoleYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5 g (15.8 mmol) 7-bromo-2,4-dichloro-5H-pyrimido[5,4-b]indole was suspended in 20 ml ethanol and mixed with 15.8 ml (31.5 mmol) 2M sodium ethylate solution (EtOH). The mixture was refluxed for 9.5 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. 5.1 g (99%) 7-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 9.5 h
  2. concentrationthe solvent was concentrated
  3. additionwater was added
  4. washwashed with water

Sources & evidence

ORD record
ord-144a92e9a70c48b78e46818f1b0da403
Source dataset
uspto-grants-2014_03
Patent number
US08664233B2

Reaction notes

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