2-methylsulfanylbenzaldehyde

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a solution of 2-(methylthio)benzaldehyde (500 mg, 3.28 mmol) in 6.6 mL of dichloromethane was added m-chlorobenzoic peracid (0.85 g, 4.9 mmol) at 0° C. After being stirred at room temperature for 1 h, the reaction mixture was diluted with ethyl acetate. The solution was washed with saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/50 to 15/85) to obtain the title compound as a white crystal (493 mg, 89%). The solution was washed with saturated NaHCO3 aqueous solution, brine dried over MgSO4 After filtration the filtrate was concentrated in vacuo the residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/50 to 15/85)

Conditions: temp:175.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-amino-4-trifluoromethylbenzenethiol hydrochloride (0.50 g), 2-methylsulfanylbenzaldehyde (0.33 g), diisopropylethylamine (0.28 g), and DMSO (4 ml) was heated to 170-180° C., and stirred with heating for 3 hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.42 g of 2-(2-methylsulfanylphenyl)-5-trifluoromethylbenzothiazole (hereinafter referred to as Present Compound 84). with heating for 3 hours Into the reaction mixture cooled to room temperature extracted with ethyl acetate The organic layer was washed with water and saturated brine dried over magnesium sulfate concentrated under reduced pressure

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of N2-methyl-5-trifluoromethylpyridin-2,3-diamine (1.34 g), 2-methylsulfanylbenzaldehyde (1.28 g), sodium hydrogen sulfite (2.19 g), and DMF (14 ml) was stirred with heating at 80° C. for 1 hour, and then heated to 120° C., and stirred with heating for further 3 hours. Into the reaction mixture cooled to room temperature, saturated aqueous ammonium chloride solution was poured, and extracted with ethyl acetate 3 times. The combined organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.74 g of 3-methyl-2-(2-methylsulfanylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 1). heated to 120° C. stirred with heating for further 3 hours Into the reaction mixture cooled to room temperature extracted with ethyl acetate 3 times The combined organic layer was dried over magnesium sulfate concentrated under reduced pressure

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

Procedure: Prepared as in example 10-10a from glycine methyl ester and 2-(methylthio)benzaldehyde. Yield 50%. MS M+H calculated 226.1; found 226.1

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

Procedure: Prepared as in example 10-10a from glycine methyl ester and 2-(methylthio)benzaldehyde. Yield 50%. MS M+H calculated 226.1; found 226.1.

Conditions: temp:175.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-amino-4-trifluoromethylbenzenethiol hydrochloride (0.50 g), 2-methylsulfanylbenzaldehyde (0.33 g), diisopropylethylamine (0.28 g), and DMSO (4 ml) was heated to 170-180° C., and stirred with heating for 3 hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.42 g of 2-(2-methylsulfanylphenyl)-5-trifluoromethylbenzothiazole (hereinafter referred to as Present Compound 84). with heating for 3 hours Into the reaction mixture cooled to room temperature extracted with ethyl acetate The organic layer was washed with water and saturated brine dried over magnesium sulfate concentrated under reduced pressure

Conditions: temp:175.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-amino-4-trifluoromethylbenzenethiol hydrochloride (0.50 g), 2-methylsulfanylbenzaldehyde (0.33 g), diisopropylethylamine (0.28 g), and DMSO (4 ml) was heated to 170-180° C., and stirred with heating for 3 hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.42 g of 2-(2-methylsulfanylphenyl)-5-trifluoromethylbenzothiazole (hereinafter referred to as Present Compound 84). with heating for 3 hours Into the reaction mixture cooled to room temperature extracted with ethyl acetate The organic layer was washed with water and saturated brine dried over magnesium sulfate concentrated under reduced pressure

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of N2-methyl-5-trifluoromethylpyridin-2,3-diamine (1.34 g), 2-methylsulfanylbenzaldehyde (1.28 g), sodium hydrogen sulfite (2.19 g), and DMF (14 ml) was stirred with heating at 80° C. for 1 hour, and then heated to 120° C., and stirred with heating for further 3 hours. Into the reaction mixture cooled to room temperature, saturated aqueous ammonium chloride solution was poured, and extracted with ethyl acetate 3 times. The combined organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.74 g of 3-methyl-2-(2-methylsulfanylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 1). heated to 120° C. stirred with heating for further 3 hours Into the reaction mixture cooled to room temperature extracted with ethyl acetate 3 times The combined organic layer was dried over magnesium sulfate concentrated under reduced pressure