Potassium Carbonate → 3-[4-(2-Methanesulfonyl-benzyloxy)-phenyl]-isoxazole-5-carboxylic acid amide

温度

40 °C

3-(4-Hydroxy-phenyl)-isoxazole-5-carboxylic acid amide (which may be prepared as described in Preparation of Intermediate 2; 50 mg, 0.245 mmol) was dissolved in DMF (1.5 mL). K2CO3 (42 mg, 0.30 mmol), tetrabutylammonium iodide (14 mg, 0.038 mmol), and 1-bromomethyl-2-methylsulfonyl-benzene (which is available from Combi-Blocks; 62 mg, 0.25 mmol) were added. The reaction mixture was heated at 40° C. for 13 h. The reaction mixture was cooled to room temperature and partitioned between H2O (5 mL) and EtOAc (5 mL). The organic layer was dried (Na2SO4), filtered, evaporated, and purified twice by chromatography (40-60% EtOAc/hexanes) to give 3-[4-(2-methanesulfonyl-benzyloxy)-phenyl]-isoxazole-5-carboxylic acid amide (3 mg, 3%) as a white powder. HRMS Calcd. for C18H17N2O5S (M+H)+, 373.0853. Found: 373.0854.

1. temperatureThe reaction mixture was cooled to room temperature
2. custompartitioned between H2O (5 mL) and EtOAc (5 mL)
3. dry with materialThe organic layer was dried (Na2SO4)
4. filtrationfiltered
5. customevaporated
6. custompurified twice by chromatography (40-60% EtOAc/hexanes)

ORDレコード

ord-e3fc7104554e46f89e32614ad9c30756

出典データセット

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09296711B2