3H-imidazo[1,2-a]pyridin-2-one;hydrobromide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 100 mg (0.47 mmol) of imidazo[1,2-a]pyridin-2-one hydrobromide salt and 122 mg (0.47 mmol) 3-bromomethyl-5-chloro-benzo[b]thiophene in 5 mL of THF is treated with 1 mL (1.0 mmol) of 1M lithium bis(trimethylsilyl)amide THF solution at −78° C. The resulting mixture is stirred this temperature for 1 h and the mixture is quenched with saturated ammonium chloride solution. The product is extracted with ethyl acetate. The organic layer is washed with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue is purified by flash chromatography to give the desired compound. the mixture is quenched with saturated ammonium chloride solution The product is extracted with ethyl acetate The organic layer is washed with water and brine dried over sodium sulfate filtered concentrated in vacuo The residue is purified by flash chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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. is heated at reflux for 1 h The precipitate is collected The solid is collected washed with water

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1 g (4.7 mmol) of imidazo[1,2-a]pyridin-2-one hydrobromide salt and 726 mg (4.7 mmol) of 1-naphthaldehyde in 20 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 precipitated solid is collected and washed with water to give the desired compound. is heated at reflux for 1 h The precipitate is collected The precipitated solid is collected washed with water

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 9 g (34.4 mmol) of (2-imino-2H-pyridin-1-yl)-acetic acid ethyl ester hydrobromide salt in 200 mL of ethanol is heated at reflux for 18 h. The reaction mixture is then cooled to room temperature and the precipitate is collected. The isolated solid is washed with ethanol to give the desired compound. at reflux for 18 h the precipitate is collected The isolated solid is washed with ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 100 mg (0.47 mmol) of imidazo[1,2-a]pyridin-2-one hydrobromide salt and 122 mg (0.47 mmol) 3-bromomethyl-5-chloro-benzo[b]thiophene in 5 mL of THF is treated with 1 mL (1.0 mmol) of 1M lithium bis(trimethylsilyl)amide THF solution at −78° C. The resulting mixture is stirred this temperature for 1 h and the mixture is quenched with saturated ammonium chloride solution. The product is extracted with ethyl acetate. The organic layer is washed with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue is purified by flash chromatography to give the desired compound. the mixture is quenched with saturated ammonium chloride solution The product is extracted with ethyl acetate The organic layer is washed with water and brine dried over sodium sulfate filtered concentrated in vacuo The residue is purified by flash chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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. is heated at reflux for 1 h The precipitate is collected The solid is collected washed with water

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1 g (4.7 mmol) of imidazo[1,2-a]pyridin-2-one hydrobromide salt and 726 mg (4.7 mmol) of 1-naphthaldehyde in 20 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 precipitated solid is collected and washed with water to give the desired compound. is heated at reflux for 1 h The precipitate is collected The precipitated solid is collected washed with water

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 9 g (34.4 mmol) of (2-imino-2H-pyridin-1-yl)-acetic acid ethyl ester hydrobromide salt in 200 mL of ethanol is heated at reflux for 18 h. The reaction mixture is then cooled to room temperature and the precipitate is collected. The isolated solid is washed with ethanol to give the desired compound. at reflux for 18 h the precipitate is collected The isolated solid is washed with ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 100 mg (0.47 mmol) of imidazo[1,2-a]pyridin-2-one hydrobromide salt and 122 mg (0.47 mmol) 3-bromomethyl-5-chloro-benzo[b]thiophene in 5 mL of THF is treated with 1 mL (1.0 mmol) of 1M lithium bis(trimethylsilyl)amide THF solution at −78° C. The resulting mixture is stirred this temperature for 1 h and the mixture is quenched with saturated ammonium chloride solution. The product is extracted with ethyl acetate. The organic layer is washed with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue is purified by flash chromatography to give the desired compound. the mixture is quenched with saturated ammonium chloride solution The product is extracted with ethyl acetate The organic layer is washed with water and brine dried over sodium sulfate filtered concentrated in vacuo The residue is purified by flash chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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. is heated at reflux for 1 h The precipitate is collected The solid is collected washed with water

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1 g (4.7 mmol) of imidazo[1,2-a]pyridin-2-one hydrobromide salt and 726 mg (4.7 mmol) of 1-naphthaldehyde in 20 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 precipitated solid is collected and washed with water to give the desired compound. is heated at reflux for 1 h The precipitate is collected The precipitated solid is collected washed with water

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 9 g (34.4 mmol) of (2-imino-2H-pyridin-1-yl)-acetic acid ethyl ester hydrobromide salt in 200 mL of ethanol is heated at reflux for 18 h. The reaction mixture is then cooled to room temperature and the precipitate is collected. The isolated solid is washed with ethanol to give the desired compound. at reflux for 18 h the precipitate is collected The isolated solid is washed with ethanol