Potassium Phosphate, Tribasic → Ethyl 5-(4-methyl-3,5-diphenyl-1H-pyrazol-1-yl)thiophene-2-carboxylate

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.

1. customthe mixture was irradiated with microwave irradiation for 45 minutes at 185° C
2. extractionThe mixture was extracted with ethyl acetate (3×2 mL)
3. washwashed with brine (5 mL)
4. dry with materialdried (MgSO4)
5. customthe mixture was evaporated
6. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate 85:15)

ORD 기록

ord-16949cf47bf949269fba50c1a2374db3

출처 데이터셋

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07994202B2