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

HRID 1016642

Reaction equation

HRID 1016642 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 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2-bromo-1-(4-methylphenyl)ethanone (99.3 g, 0.47 mol) in dimethylformamide (250 mL) was added slowly to a solution of 5-methyl-2-pyridinamine (50.4 g, 0.47 mol) in dimethylformamide (250 mL). Sodium hydrogen carbonate (78.3 g, 0.93 mol) was added in portions and the mixture was stirred at room temperature for 15 min., then under reflux for 1.5 h. The mixture was cooled and poured into water (2500 mL). The solid was collected, washed with water (1000 mL) and recrystallised from dimethylformamide (400 mL). The solid was collected and dried in vacuo at 120° C. to give the title compound (89 g, 86%). 1H NMR (360 MHz, DMSO-d6) δ 8.30 (1H, d, J 1.5 Hz), 8.23 (1H, s), 7.84 (2H, d, J 8.0 Hz), 7.47 (1H, d, J 9.2 Hz), 7.25 (2H, d, J 8.0 Hz), 7.09 (1H, dd, J 9.2, 1.5 Hz), 2.33 (3H, s), and 2.28 (3H, s).

Workup

  1. temperatureunder reflux for 1.5 h
  2. temperatureThe mixture was cooled
  3. customThe solid was collected
  4. washwashed with water (1000 mL)
  5. customrecrystallised from dimethylformamide (400 mL)
  6. customThe solid was collected
  7. customdried in vacuo at 120° C.

Sources & evidence

ORD record
ord-e8d4952219b74732a4bd9df57ceef865
Source dataset
uspto-grants-2002_11
Patent number
US06476045B2

Linked notes

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