Tetrahydrofuran → 3-Methyl-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxylic acid

HRID 1851445Notes

Reaction equation

[CH3:1][C:2]1[C:10]2[C:5](=[C:6]([NH:11][S:12]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)(=[O:14])=[O:13])[CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:20]([O:22]CC)=[O:21].[OH-].[Na+].O1CCCC1>C(O)C>[CH3:1][C:2]1[C:10]2[C:5](=[C:6]([NH:11][S:12]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)(=[O:14])=[O:13])[CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:20]([OH:22])=[O:21]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of ethyl 3-methyl-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxylate (1.33 g), 8N aqueous sodium hydroxide solution (2.0 mL), tetrahydrofuran (5 mL) and ethanol (10 mL) was stirred at 60° C. for 3 hr. The reaction mixture was concentrated, and water was added to the residue. The mixture was acidified with 10% aqueous citric acid solution, and the resulting crystals were filtrated, washed with water, and dried to give the title compound (1.15 g, yield 94%) as colorless crystals. melting point>263° C. (decomposition).

Workup

concentrationThe reaction mixture was concentrated
additionwater was added to the residue
filtrationthe resulting crystals were filtrated
washwashed with water
customdried

Sources & evidence

ORD record: ord-efccaf19511c463c8a5192c8725f8f2a
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957070B2

Reaction notes

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