1-Methyl-2-[(2,4,6-trifluorophenyl)methylidene]hydrazine → 4,6-Difluoro-1-methyl-1H-indazole

HRID 1959642Notes

Reaction equation

HRID 1959642 reaction equation
[CH3:1][NH:2]/[N:3]=[CH:4]/[C:5]1[C:10](F)=[CH:9][C:8]([F:12])=[CH:7][C:6]=1[F:13]>C(Cl)Cl>[F:13][C:6]1[CH:7]=[C:8]([F:12])[CH:9]=[C:10]2[C:5]=1[CH:4]=[N:3][N:2]2[CH3:1]

Participants

3

Reactant 1

HCID 871331261-Methyl-2-[(2,4,6-trifluorophenyl)methylidene]hydrazine

Product 1

HCID 579174794,6-Difluoro-1-methyl-1H-indazoleYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Methyl-N′-[1-(2,4,6-trifluoro-phenyl)-meth-(E)-ylidene]-hydrazine (3.85 g, 20.46 mmol) was heated in a sealed tube at 210° C. for 2 h. After cooling, the black residue was dissovled in DCM and purified by flash chromatography (EtOAc:hexane 10:90) to give the title compound as a light yellow crystal (1.926 g, 56%). 1H-NMR (400 MHz, MeOH-d4) δ ppm 8.05 (s, 1H), 7.16 (d, 1H), 6.75 (t, 1H), 3.32 (s, 3H). LCMS (method B): [MH]+=169, tR=2.28 min.

Workup

  1. temperatureAfter cooling
  2. custompurified by flash chromatography (EtOAc:hexane 10:90)

Sources & evidence

ORD record
ord-0acf8c56721945a398deef8126b8552d
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

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