(1S,2S)-(+)-N,N-Dimethylcyclohexane-1,2-diamine

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

Procedure: To a solution of 3-phenyl-1H-indazole (50 mg) synthesized according to the literature (T. Edward C., et al., Tetrahedron, 1991, 47, 9599-9620) in N,N-dimethylacetamide (500 μL, manufactured by Kanto Chemical Co., Inc.), potassium phosphate (85 mg, manufactured by Wako Pure Chemical Industries, Ltd.), (1S,2S)-(+)-N,N-dimethylcyclohexane-1,2-diamine (5 mg, manufactured by Tokyo Chemical Industry Co., Ltd.), copper iodide (4 mg, manufactured by Kanto Chemical Co., Inc.), and ethyl 5-bromothiophene-2-carboxylate (45 mg, manufactured by Alfa Aesar GmbH & Co. KG) were added, and the mixture was irradiated with microwave irradiation for 45 minutes at 185° C. The reaction solution was cooled to room temperature, and then water (1 mL) was added thereto. The mixture was extracted with ethyl acetate (3×2 mL), washed with brine (5 mL), and dried (MgSO4), and then the mixture was evaporated. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate 85:15), to give 50 mg of the title compound. LC-MS: HPLC retention time 6.52 minutes, m/z 349 (M+H), condition A-1. the mixture was irradiated with microwave irradiation for 45 minutes at 185° C The mixture was extracted with ethyl acetate (3×2 mL) washed with brine (5 mL) dried (MgSO4) the mixture was evaporated The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate 85:15)

Conditions: temp:180.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-phenyl-1H-indazole (689 mg) synthesized according to the literature (T. Edward C., et al., Tetrahedron, 1991, 47, 9599-9620) in mesitylene (5 mL, manufactured by Kanto Chemical Co., Inc.), potassium phosphate (2.38 g, manufactured by Wako Pure Chemical Industries, Ltd.), (1S,2S)-(+)-N,N-dimethylcyclohexane-1,2-diamine (50 mg, manufactured by Tokyo Chemical Industry Co., Ltd.), copper iodide (34 mg, manufactured by Kanto Chemical Co., Inc.), and ethyl 2-bromo-4-thiazolecarboxylate (840 mg) synthesized according to the literature (T. R. Kelly, et al., J. Org. Chem., 1996, 61, 4623-4633) were added, and the mixture was heated overnight at 180° C. The reaction solution was cooled to room temperature, and then water (20 mL) was added thereto. Ethyl acetate was extracted (3×20 mL), washed with brine (20 mL), and dried (MgSO4), and then the solvent was evaporated. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1), to give 579 mg of the title compound. LC-MS: HPLC retention time 6.80 minutes, m/z 350 (M+H), condition B-1. , 1996, 61, 4623-4633) were added The reaction solution was cooled to room temperature Ethyl acetate was extracted (3×20 mL) washed with brine (20 mL) dried (MgSO4) the solvent was evaporated The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)