Acetic Acid → 3-(3-fluorophenyl)-7-methoxy-1H-indazole-5-carboxylic acid

HRID 1610127Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:11](=[C:12]([O:19][CH3:20])[CH:13]=C(C#N)[CH:15]=3)[NH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:21]([OH:24])(=[O:23])[CH3:22].S(=O)(=O)(O)O>O>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:11](=[C:12]([O:19][CH3:20])[CH:13]=[C:22]([C:21]([OH:24])=[O:23])[CH:15]=3)[NH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To 450 mg of 3-(3-fluorophenyl)-7-methoxy-1H-indazole-5-carbonitrile were sequentially added 6 ml of glacial acetic acid, 2 ml of water and 2 ml of concentrated sulfuric acid, followed by stirring at 100° C. for one day. After standing to cool, water was added to the reaction mixture and the resulting crystals were collected by filtration. The crystals were sequentially washed with isopropanol and diethyl ether, to give 428 mg of the title compound as colorless crystals.

Workup

temperatureto cool
filtrationthe resulting crystals were collected by filtration
washThe crystals were sequentially washed with isopropanol and diethyl ether

Sources & evidence

ORD record: ord-ad4cb56c66804292881748df13d29d9d
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06982274B2

Reaction notes

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