Bromine → 5-bromo-6-fluoro-1H-indazole-3-carboxylic acid

HRID 1054838Notes

Reaction equation

[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([OH:13])=[O:12])=[N:7][NH:8]2)=[CH:4][CH:3]=1.[Br:14]Br>C(O)(=O)C>[Br:14][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:2]=1[F:1])[NH:8][N:7]=[C:6]2[C:11]([OH:13])=[O:12]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 6-fluoro-1H-indazole-3-carboxylic acid (4.95 g, 23.8 mmol) and acetic acid (50 mL) was treated with bromine (2.0 mL, 38 mmol) dropwise at room temperature. The reaction mixture was heated to 90° C. and stirred for 16 hours under an atmosphere of nitrogen. The reaction mixture was then exposed to the atmosphere and stirred at 95° C. for 72 hours. The resulting solids were collected while the reaction mixture was still hot and rinsed with diethyl ether two times. The solids were dried at 50° C. under reduced pressure to give the title compound (2.89 g). 1H NMR (500 MHz, DMSO-d6) δ 8.31 (d, J=6.8 Hz, 1H), 7.71 (d, J=8.8 Hz, 1H).

Workup

stirringstirred at 95° C. for 72 hours
customThe resulting solids were collected while the reaction mixture
washrinsed with diethyl ether two times
customThe solids were dried at 50° C. under reduced pressure

Sources & evidence

ORD record: ord-850fbc3dd4644b1792ee3bbd8adbf705
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394285B2

Reaction notes

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