2-Aminopyridine → HCID 71295498, compound

HRID 1776884Notes

Reaction equation

HRID 1776884 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:6]=1[O:12][CH3:13])=O.[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH2:20]>CCO>[Br:11][C:9]1[CH:8]=[CH:7][C:6]([O:12][CH3:13])=[C:5]([C:3]2[N:20]=[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][N:14]3[CH:2]=2)[CH:10]=1

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 27568502-bromo-1-(5-bromo-2-methoxyphenyl)ethanone

Product 1

HCID 71295498HCID 71295498, compoundYield 6.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 2-bromo-1-(5-bromo-2-methoxyphenyl)ethanone (500 mg, 1.6 mmol) in EtOH (5 mL), pyridin-2-amine (153 mg, 1.6 mmol) was added. The mixture was stirred at 80° C. for 12 hours, and then cooled to 25° C. After filtrated, the solid was dried in vacuo to provide 2-(5-bromo-2-methoxyphenyl)imidazo[1,2-a]pyridine (30 mg, yield: 5%). 1H-NMR(CDCl3, 400 MHz) δ 8.54 (s, 1H), 8.18 (s, 1H), 8.12˜8.13 (m, 1H), 7.62˜7.64 (m, 1H), 7.37˜7.40 (m, 1H), 7.16˜7.21 (m, 1H), 6.86˜6.88 (m, 1H), 6.76˜6.79 (m, 1H), 3.98 (s, 3H). MS (M+H)+: 303/305.

Workup

  1. additionwas added
  2. temperaturecooled to 25° C
  3. filtrationAfter filtrated
  4. customthe solid was dried in vacuo

Sources & evidence

ORD record
ord-669232c4af734a61b282acdd72fff4ad
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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