Bromomethyl 4-methoxyphenyl ketone → 2-(4-Methoxyphenyl)-6-methylimidazo[1,2-a]pyridine

HRID 230253Notes

Reaction equation

HRID 230253 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=O.[CH3:13][C:14]1[CH:15]=[CH:16][C:17]([NH2:20])=[N:18][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>CCO>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:20]=[C:17]3[CH:16]=[CH:15][C:14]([CH3:13])=[CH:19][N:18]3[CH:2]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 10340Sodium CarbonateHCID 153482-Amino-5-methylpyridine

Product 1

HCID 7359102-(4-Methoxyphenyl)-6-methylimidazo[1,2-a]pyridineYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a magnetically stirred solution of 2-bromo-1-(4-methoxy-phenyl)-ethanone (3.0 g, 13.09 mmol) and 5-methyl-pyridin-2-ylamine (1.42 g, 13.09 mmol) in EtOH (30 mL) under Ar atmosphere was added sodium carbonate (2.77 g, 26.18 mmol). The reaction mixture was refluxed for 4 h. The mixture was cooled to room temperature and concentrated in vacuo. Water (60 mL) was added, and the aqueous phase was extracted with dichloromethane (100 mL). The combined organic layers were washed with water (100 mL), dried (MgSO4), and concentrated in vacuo to provide the title compound (2.8 g, 90%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 2.27 (s, 3H), 3.82 (s, 3H), 6.95 (m, 3H), 7.48 (d, J=8.8 Hz, 1H), 7.65 (s, 1H), 7.85 (m, 3H).

Workup

  1. temperatureThe reaction mixture was refluxed for 4 h
  2. concentrationconcentrated in vacuo
  3. additionWater (60 mL) was added
  4. extractionthe aqueous phase was extracted with dichloromethane (100 mL)
  5. washThe combined organic layers were washed with water (100 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c89abc8ae7734c4f8f9ab2a95b63caba
Source dataset
uspto-grants-2009_07
Patent number
US07566725B2

Reaction notes

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