Tetrahydrofuran → 7-{[(5-Chloro-2-thienyl)sulfonyl]amino}-1H-indole-2-carboxylic acid

HRID 1851449Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of ethyl 7-{[(5-chloro-2-thienyl)sulfonyl]amino}-1H-indole-2-carboxylate (1.03 g), 8N aqueous sodium hydroxide solution (1.3 mL), tetrahydrofuran (5 mL) and ethanol (15 mL) was stirred at 60° C. for 2 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 (0.92 g, yield 90%) as colorless crystals. melting point>277° 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-962c90df62b2416a9bb034b994beadb2
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957070B2

Reaction notes

Loading…