Water → 6-bromo-3H-imidazo[4,5-b]pyridin-2-ol

HRID 1910675Notes

Reaction equation

HRID 1910675 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[N:6][CH:7]=1.[C:10](N1C=CN=C1)(N1C=CN=C1)=[O:11].O>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[NH:9][C:10](=[O:11])[NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 6911565-Bromopyridine-2,3-diamine

Product 1

HCID 19244136-bromo-3H-imidazo[4,5-b]pyridin-2-olYield 92.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Bromopyridine-2,3-diamine (2.45 g) was dissolved in THF (25 mL) and 1,1′-carbonyldiimidazole (2.54 g, 1.2 eq) was added. The reaction was stirred at room temperature under nitrogen gas overnight. Water was then added to the mixture and the product was collected by filtration. The solid was dried under vacuum delivering product (2.57 g, 92% yield). 1H-NMR (300 MHz, DMSO-d6) δ 11.50 (s, 1H), 11.00 (s, 1H), 7.93 (s, 1H), 7.39 (s, 1H). MS (ES+) m/z 213.1 (M+1).

Workup

  1. filtrationthe product was collected by filtration
  2. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-888151648baf4ce2b0ecec3dd4149bce
Source dataset
uspto-grants-2013_12
Patent number
US08604023B2

Reaction notes

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