Sodium ethoxide → HCID 58118496, compound

HRID 1182831Notes

Reaction equation

HRID 1182831 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:17][CH3:18])[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.[CH3:19][CH2:20][O-:21].[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([O:17][CH3:18])[C:5]2[C:6]3[N:14]=[C:13]([Cl:15])[N:12]=[C:11]([O:21][CH2:20][CH3:19])[C:7]=3[NH:8][C:9]=2[CH:10]=1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 58118504HCID 58118504, compound

Product 1

HCID 58118496HCID 58118496, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

600 mg (1.7 mmol) 7-bromo-2,4-dichloro-9-methoxy-5H-pyrimido[5,4-b]indole was suspended in 20 ml ethanol and mixed with 174 mg (2.6 mmol) sodium ethylate. The mixture was refluxed for 3 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. 450 mg (73%) 7-bromo-2-chloro-4-ethoxy-9-methoxy-5H-pyrimido[5,4-b]indole was obtained. ESI-MS [m/z]: 354, 356 [M−H]−

Workup

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

Sources & evidence

ORD record
ord-89e81a54aa084dfaac07d5545cd2946a
Source dataset
uspto-grants-2014_03
Patent number
US08664233B2

Reaction notes

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