Tetrahydrofuran → 5-[4-(Methylsulfonyl)phenoxy]-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indole-2-carboxylic acid

HRID 1042098Notes

Reaction equation

[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:11][C:12]2[CH:13]=[C:14]3[C:18](=[C:19]([O:21][CH:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[CH:20]=2)[NH:17][C:16]([C:28]([O:30]CC)=[O:29])=[CH:15]3)=NC=1)(=[O:4])=[O:3].[OH-].[Na+].O1CC[CH2:37][CH2:36]1>C(O)C>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:11][C:12]2[CH:13]=[C:14]3[C:18](=[C:19]([O:21][CH:22]4[CH2:23][CH2:24][O:25][CH2:26][CH2:27]4)[CH:20]=2)[NH:17][C:16]([C:28]([OH:30])=[O:29])=[CH:15]3)=[CH:37][CH:36]=1)(=[O:3])=[O:4]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of ethyl 5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indole-2-carboxylate (5.33 g), 1M aqueous sodium hydroxide solution (20 mL), tetrahydrofuran (20 mL), and ethanol (20 mL) was stirred at 60° C. for 40 min. The reaction solution was concentrated under reduced pressure, and the residue was dissolved in water, and washed with ethyl acetate. To the aqueous layer was added 1M hydrochloric acid (30 mL), and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound (1.95 g, yield 74%) as an orange amorphous solid.

Workup

concentrationThe reaction solution was concentrated under reduced pressure
dissolutionthe residue was dissolved in water
washwashed with ethyl acetate
additionTo the aqueous layer was added 1M hydrochloric acid (30 mL)
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-fb1034165f5c4f1d8db26b20f4279058
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557805B2

Reaction notes

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