Water → 6-Methyl-2-(4-methylphenyl)imidazo(1,2-a)pyridine

HRID 500750

Reaction equation

HRID 500750 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1)=O.[CH3:12][C:13]1[CH:14]=[CH:15][C:16]([NH2:19])=[N:17][CH:18]=1.C([O-])(O)=O.[Na+].O>CN(C)C=O>[CH3:12][C:13]1[CH:14]=[CH:15][C:16]2[N:17]([CH:2]=[C:3]([C:5]3[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=3)[N:19]=2)[CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 153482-Amino-5-methylpyridineHCID 692722-Bromo-4'-methylacetophenoneHCID 516892Sodium Bicarbonate

Product 1

HCID 6677206-Methyl-2-(4-methylphenyl)imidazo(1,2-a)pyridineYield 70.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2-bromo-1-p-tolyl-ethanone (500 mg, 2.3 mmol) in dimethylformamide (2 mL) was added slowly to a solution of 5-methyl-pyridin-2-yl-amine (249 mg, 2.3 mmol) in dimethylformamide (2 mL). NaHCO3 (386 mg, 4.6 mmol) was added in portions and the mixture was stirred at room temperature for 15 minutes, then at reflux for 1.5 hours. The mixture was cooled and poured into water (5 mL). The solid was collected, washed with water (2 mL) and recrystallized from dimethylformamide (5 mL) to yield the desired product 6-methyl-2-p-tolyl-imidazo[1,2-a]pyridine (360 mg, 70%). 1H NMR (300 MHz, DMSO-d6) δ 2.27 (s, 3H), 2.32 (s, 3H), 7.08 (d, 1H), 7.21 (d, 2H), 7.46 (d, 1H), 7.83 (d, 2H), 8.24 (s, 1H), 8.29 (s, 1H); ESI-MS (MH+), 223.

Workup

  1. temperatureat reflux for 1.5 hours
  2. temperatureThe mixture was cooled
  3. customThe solid was collected
  4. washwashed with water (2 mL)
  5. customrecrystallized from dimethylformamide (5 mL)

Sources & evidence

ORD record
ord-6133d36d4b3b41f0bce50c83586cf962
Source dataset
uspto-grants-2010_08
Patent number
US07772248B2

Linked notes

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