Sodium Hydroxide → 7-[2-Methoxy-1-(methoxymethyl)ethoxy]-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxylic acid

Temperature

50 °C

To a solution of methyl 7-[2-methoxy-1-(methoxymethyl)ethoxy]-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxylate (1.79 g) in a mixture of tetrahydrofuran (20 mL) and methanol (15 mL) was added 1M aqueous sodium hydroxide solution (15 mL), and the mixture was stirred at 50° C. for 30 min. The mixture was concentrated under reduced pressure and the residue was dissolved in water. The mixture was washed with diethyl ether three times. The diethyl ether layers were combined and extracted with water. The aqueous layers were combined and 1M hydrochloric acid (15 mL) was added to the mixture. The resulting white suspension was filtered to give the title compound (1.02 g, 69%) as a pale orange solid. MS 451 (MH+).

1. concentrationThe mixture was concentrated under reduced pressure
2. dissolutionthe residue was dissolved in water
3. washThe mixture was washed with diethyl ether three times
4. extractionextracted with water
5. addition1M hydrochloric acid (15 mL) was added to the mixture
6. filtrationThe resulting white suspension was filtered

ORD record

ord-dd3975aca8fe4d59a442136936565865

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08673942B2