2-Aminopyridine → HCID 178517590, compound

HRID 1776893Notes

Reaction equation

HRID 1776893 reaction equation
Br[CH2:2][C:3]([C:5]1[C:6]([OH:12])=[N:7][CH:8]=[C:9]([Br:11])[CH:10]=1)=O.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1>CCO>[Br:11][C:9]1[CH:10]=[C:5]([C:3]2[N:13]=[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]3[CH:2]=2)[C:6]([OH:12])=[N:7][CH:8]=1

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 178520129HCID 178520129, compound

Product 1

HCID 178517590HCID 178517590, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-(5-bromo-2-hydroxypyridin-3-yl)ethanone (300 mg, 1.02 mmol) and 2-aminopyridine (100 mg, 1.06 mmol) in EtOH (10 mL) was stirred at reflux overnight. The reaction mixture was cooled and filtered to provide 5-bromo-3-(imidazo[1,2-a]pyridin-2-yl)pyridin-2-ol (200 mg, yield: 67%). 1H-NMR (DMSO, 400 MHz) δ 12.75 (br s, 1H), 9.02 (s, 1H), 8.94 (d, J=6.8 Hz, 1H), 8.42 (d, J=2.8 Hz, 1H), 7.89˜7.96 (m, 3H), 7.45 (d, J=4.8 Hz, 1H). MS (M+H)+: 290/292.

Workup

  1. temperatureat reflux overnight
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-6a1e47285d134d5dbc5ac6cb1444f426
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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