Acetic Acid → 1h-Indazole-5-carboxylic acid,1-acetyl-3-(4-fluorophenyl)-

HRID 1353683Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a flask containing 3-(4-fluorophenyl)-1H-indazole-5-carboxylic acid (5.0 g, 0.02 mol) was added acetic acid (100 mL). The flask was placed under nitrogen and to the flask was added acetic anhydride (5.6 mL, 0.06 mol). The reaction refluxed at 80° C. for three hours. The flask was cooled to room temperature and the reaction was diluted with water. The product was collected by vacuum filtration and rinsed with additional amounts of water to yield the title compound (5.96 g, 100% yield) 1H NMR (DMSO-d6) δ 8.6 (s, 1H), 8.45–8.5 (d, 1H), 8.2–8.25 (d, 1H), 8.1 (m, 2H), 7.5 (t, 2H), 2.8 (s, 3H).

Workup

temperatureThe flask was cooled to room temperature
filtrationThe product was collected by vacuum filtration
washrinsed with additional amounts of water

Sources & evidence

ORD record: ord-f20eeed70aaf4fc1ad2ce4e889baa06f
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07220771B2

Reaction notes

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