Sodium Hydroxide → 5-Bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxylic acid

온도

85 °C

A solution of 6 M NaOH (12 mL, 72.0 mmol) was added to a suspension of 1-(1,1-dimethylethyl) 7-methyl 5-bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-1,7-dicarboxylate (0.93 g, 1.912 mmol) and 1-(1,1-dimethylethyl) 7-ethyl 5-bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-1,7-dicarboxylate (3.08 g, 6.16 mmol) in MeOH (50 mL) and water (25 mL) in a 250 mL round bottomed flask fitted with a reflux condenser. The reaction was heated at 85° C. (bath temp) for 1.5 h. The MeOH was removed by rotovap, and a solution of 6 M HCl was added until the mixture had attained a pH of ˜1 by pH paper. The yellow solid was filtered off, and the filtrate was extracted with EtOAc (3×10 mL). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure, and the residue was combined with the precipitate from the filtration and dried under house vacuum at 45° C. overnight. Recovered 2.98 g (86%) of the title compound.

1. customfitted with a reflux condenser
2. customThe MeOH was removed by rotovap
3. additiona solution of 6 M HCl was added until the mixture
4. filtrationThe yellow solid was filtered off
5. extractionthe filtrate was extracted with EtOAc (3×10 mL)
6. dry with materialThe combined organic layers were dried (Na2SO4)
7. concentrationconcentrated under reduced pressure
8. filtrationthe residue was combined with the precipitate from the filtration
9. customdried under house vacuum at 45° C. overnight
10. customRecovered 2.98 g (86%) of the title compound

ORD 기록

ord-9f88d72c49364e71be998890b8bb3160

출처 데이터셋

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08372875B2