Imidazo[1,2-a]pyridin-2(3H)-one--hydrogen bromide (1/1) → 3-(4-Methyl-benzo[b]thiophen-3-ylmethylene)-imidazo[1,2-a]pyridin-2-one

HRID 215971Notes

Reaction equation

HRID 215971 reaction equation
Br.[N:2]1[C:3](=[O:11])[CH2:4][N:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=12.[CH3:12][C:13]1[C:21]2[C:20]([CH:22]=O)=[CH:19][S:18][C:17]=2[CH:16]=[CH:15][CH:14]=1>C(O)C>[CH3:12][C:13]1[C:21]2[C:20]([CH:22]=[C:4]3[N:5]4[CH:10]=[CH:9][CH:8]=[CH:7][C:6]4=[N:2][C:3]3=[O:11])=[CH:19][S:18][C:17]=2[CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 44121307Imidazo[1,2-a]pyridin-2(3H)-one--hydrogen bromide (1/1)HCID 579956704-Methyl-benzo[b]thiophene-3-carbaldehyde

Product 1

HCID 686997973-(4-Methyl-benzo[b]thiophen-3-ylmethylene)-imidazo[1,2-a]pyridin-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.6 g (7.4 mmol) of imidazo[1,2-a]pyridin-2-one hydrobromide salt and 1.2 g (6.7 mmol) of 4-methyl-benzo[b]thiophene-3-carbaldehyde in 40 mL of ethanol is heated at reflux for 1 h and then cooled to room temperature. The precipitate is collected. The isolated solid is suspended in 40 mL of 2M potassium carbonate solution and the resulting mixture is stirred for 48 h at room temperature. The solid is collected and washed with water to give the desired compound.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1 h
  3. customThe precipitate is collected
  4. customThe solid is collected
  5. washwashed with water

Sources & evidence

ORD record
ord-c87e87eadcd744539f716a1f867b5e61
Source dataset
uspto-grants-2012_06
Patent number
US08193214B2

Reaction notes

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