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

HRID 1182857Notes

Reaction equation

HRID 1182857 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]=[C:13]([CH:15]4[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]4)[N:12]=[C:11](Cl)[C:7]=3[NH:8][C:9]=2[CH:10]=1.[CH3:22][CH2:23][O-:24].[Na+]>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]=[C:13]([CH:15]4[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]4)[N:12]=[C:11]([O:24][CH2:23][CH3:22])[C:7]=3[NH:8][C:9]=2[CH:10]=1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 866501997-bromo-4-chloro-2-(4-piperidyl)-5H-pyrimido[5,4-b]indole

Product 1

HCID 668635427-bromo-4-ethoxy-2-(4-piperidyl)-5H-pyrimido[5,4-b]indole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

300 mg (0.82 mmol) 7-bromo-4-chloro-2-(4-piperidyl)-5H-pyrimido[5,4-b]indole was mixed with an excess of 2 M NaOEt and kept at reflux for 2 h. Then, water was added and the solvent was removed in vacuo. Following LC (CH2Cl2/MeOH, 0-50%), 160 mg (52%) of the title substance was obtained ESI-MS [m/z]: 375, 377 [M+H]+

Workup

  1. temperatureat reflux for 2 h
  2. customthe solvent was removed in vacuo
  3. customFollowing LC (CH2Cl2/MeOH, 0-50%), 160 mg (52%) of the title substance was obtained ESI-MS [m/z]

Sources & evidence

ORD record
ord-245c04e82887444ba9e66b8a2ef82225
Source dataset
uspto-grants-2014_03
Patent number
US08664233B2

Reaction notes

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