Ethyl Acetate → 3-(3-fluorophenyl)-6-nitro-1H-indazole

HRID 503129Notes

Reaction equation

Br[C:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[NH:4][N:3]=1.[F:14][C:15]1[CH:16]=[C:17]([Sn](CCCC)(CCCC)CCCC)[CH:18]=[CH:19][CH:20]=1.C(OCC)(=O)C>CN1CCCC1=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:14][C:15]1[CH:20]=[C:19]([C:2]2[C:10]3[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=3)[NH:4][N:3]=2)[CH:18]=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 180 °C

Procedure

To a solution of 1.0 g of 3-bromo-6-nitro-1H-indazole in 10 ml N-methylpyrrolidone were added 2.0 g of (3-fluorophenyl)tri-n-butyltin, and 480 mg of tetrakis(triphenylphosphine)palladium(0), and the mixture was stirred at 180° C. for 2 hours. To the reaction mixture was added 60 ml of ethyl acetate. The mixture was sequentially washed with water (×2) and brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography (ethyl acetate:toluene=1:49), to give 302 mg of the title compound as orange crystals.

Workup

washThe mixture was sequentially washed with water (×2) and brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated
customThe crude product was purified
customseparated by silica gel column chromatography (ethyl acetate:toluene=1:49)

Sources & evidence

ORD record: ord-93c56cabe48a441a80a5927dd683c736
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07776890B2

Reaction notes

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