Water → HCID 66898207, compound

Temperature

0 °C

To a solution of methyl 7-hydroxy-5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-1H-indole-2-carboxylate (3.12 g) in a mixture of tetrahydrofuran (30 mL) and methanol (5 mL) was added dropwise 2M trimethylsilyldiazomethane diethyl ether solution (4.3 mL) at 0° C. The mixture was stirred at 0° C. for 1 h, 2M trimethylsilyldiazomethane diethyl ether solution (8.0 mL) was added dropwise to the mixture again, and the mixture was stirred at 0° C. for 2.5 h. Furthermore, 2M trimethylsilyldiazomethane diethyl ether solution (4.0 mL) was added dropwise to the mixture, and the mixture was stirred at room temperature for 1 h. To quench the reaction, 6M hydrochloric acid (9 mL) was added to the mixture. Water was added and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium carbonate solution and saturated brine, dried over magnesium sulfate, filtered and concentrated. The residual solid was washed with diethyl ether to give the title compound (2.78 g, 86%) as a brown solid. MS 377 (MH+).

1. stirringthe mixture was stirred at 0° C. for 2.5 h
2. stirringthe mixture was stirred at room temperature for 1 h
3. customTo quench
4. customthe reaction, 6M hydrochloric acid (9 mL)
5. additionwas added to the mixture
6. extractionthe mixture was extracted with ethyl acetate
7. washThe organic layer was washed successively with saturated aqueous sodium carbonate solution and saturated brine
8. dry with materialdried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated
11. washThe residual solid was washed with diethyl ether

ORD record

ord-46fd686f5dd74e1ea6e7b0b20f81af9c

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08673942B2