Di(succinimido) carbonate → 6-bromo-3H-imidazo[4,5-b]pyridin-2-ol

HRID 912982Notes

Reaction equation

HRID 912982 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1.[C:10](=O)(ON1C(=O)CCC1=O)[O:11]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:9][C:5]1[CH:6]=[C:7]2[NH:8][C:10](=[O:11])[NH:1][C:2]2=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 676246Di(succinimido) carbonateHCID 6911565-Bromopyridine-2,3-diamine

Product 1

HCID 19244136-bromo-3H-imidazo[4,5-b]pyridin-2-ol

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 2,3-diamino-5-bromopyridine (0.94 g, 5 mmol, Aldrich) and disuccinimido carbonate (1.28 g, 5 mmol, Aldrich) in chloroform (50 mL) was heated at reflux for 12 h. The solvent was removed in vacuo and the residue was purified by recrystallization from 40% EtOAc/hexane to give the title compound as a brown solid. MS (ESI, pos. ion) m/z: 214 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 12 h
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by recrystallization from 40% EtOAc/hexane

Sources & evidence

ORD record
ord-be0b28368dad44c5818f7699e51d58fc
Source dataset
uspto-grants-2011_09
Patent number
US08026241B2

Reaction notes

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