O-Xylene → HCID 178440402, compound

HRID 1880372Notes

Reaction equation

HRID 1880372 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([C:8](=O)[CH2:9][CH2:10][CH3:11])[CH:7]=1.C1(C)C(C)=CC=CC=1.[NH2:22][NH2:23]>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[NH:23][N:22]=[C:8]2[CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 9321HydrazineHCID 529838151-(5-Bromo-2-fluorophenyl)butan-1-one

Product 1

HCID 178440402HCID 178440402, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
65 °C

Procedure

To 1-(5-bromo-2-fluorophenyl)butan-1-one (2.0 g, 8.1 mmol) in THF, anhydrous hydrazine (11 mL) in THF was added and heated at reflux (60-70° C.) for 5-6 hours. Xylene was added to the reaction mixture and heated at reflux for 20-24 hours. The reaction mixture was concentrated to give a crude product, which was purified by column chromatography using 15% ethyl acetate/pet-ether as eluents to afford 5-bromo-3-propyl-1H-indazole (1.02 g, 52.3%) as a solid. 1H NMR (CDCl3): δ 7.9 (s, 1H), 7.4 (d, 1H), 7.3 (d, 1H), 2.9 (t, 2H), 1.8 (q, 2H), 1.0 (t, 3H).

Workup

  1. temperatureheated
  2. temperatureheated
  3. temperatureat reflux for 20-24 hours
  4. concentrationThe reaction mixture was concentrated
  5. customto give a crude product, which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-60eceb282a984d9fb3824e3c9025c7d3
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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