Phosphorus oxychloride → 7-bromo-4-chloro-2-(4-piperidyl)-5H-pyrimido[5,4-b]indole

HRID 1182856Notes

Reaction equation

HRID 1182856 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](O)[C:7]=3[NH:8][C:9]=2[CH:10]=1.O=P(Cl)(Cl)[Cl:24]>>[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:24])[C:7]=3[NH:8][C:9]=2[CH:10]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517539HCID 178517539, compound

Product 1

HCID 866501997-bromo-4-chloro-2-(4-piperidyl)-5H-pyrimido[5,4-b]indoleYield 72%

Procedure

650 mg (1.90 mmol) 7-bromo-2-(4-piperidyl)-5H-pyrimido[5,4-b]indol-4-ol were kept at reflux in POCl3 for 9 h. Then, POCl3 was removed in vacuo, the residue was mixed with water and neutralized with NaHCO3. The precipitate formed was sucked off and washed with water. 500 mg (72%) 7-bromo-4-chloro-2-(4-piperidyl)-5H-pyrimido[5,4-b]indole was obtained. ESI-MS [m/z]: 365, 367 [M+H]+

Workup

  1. customThen, POCl3 was removed in vacuo
  2. additionthe residue was mixed with water and neutralized with NaHCO3
  3. customThe precipitate formed
  4. washwashed with water

Sources & evidence

ORD record
ord-002c24c7dd454c4799b2e814e9d6f5b7
Source dataset
uspto-grants-2014_03
Patent number
US08664233B2

Reaction notes

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