Acetic Acid → 3-Benzo[b]thiophen-2-yl-1H-5-indazolecarboxylic Acid

HRID 503114Notes

Reaction equation

[S:1]1[C:5]([C:6]2[C:14]3[C:9](=[CH:10][CH:11]=C(C#N)[CH:13]=3)[NH:8][N:7]=2)=[CH:4][C:3]2[CH:17]=[CH:18][CH:19]=[CH:20][C:2]1=2.[C:21]([OH:24])(=[O:23])[CH3:22].O.S(=O)(=O)(O)O>C(OCC)(=O)C>[S:1]1[C:5]([C:6]2[C:14]3[C:9](=[CH:10][CH:11]=[C:22]([C:21]([OH:24])=[O:23])[CH:13]=3)[NH:8][N:7]=2)=[CH:4][C:3]2[CH:17]=[CH:18][CH:19]=[CH:20][C:2]1=2

Participants

Conditions

Temperature: 110 °C

Procedure

To 288 mg of 3-benzo[b]thiophen-2-yl-1H-5-indazolecarbonitrile were added 3 ml of glacial acetic acid, 1 ml of water and 0.8 ml of concentrated sulfuric acid, and the mixture was stirred at 110° C. for 4 hours. After standing to cool, the mixture was added with 120 ml of ethyl acetate, sequentially washed with water and brine, dried over anhydrous magnesium sulfate. After filtering the organic layer through a silica gel pat, the solvent was evaporated, to give 307 mg of the title compound as ocher yellow crystals.

Workup

temperatureto cool
washsequentially washed with water and brine
dry with materialdried over anhydrous magnesium sulfate
filtrationAfter filtering the organic layer through a silica gel pat
customthe solvent was evaporated

Sources & evidence

ORD record: ord-bbd7f2500aab4d89826c9607d4fbeb8c
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07776890B2

Reaction notes

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