Hydrazine hydrate (1:1) → 5-[(3,5-difluorophenyl)methyl]-1H-indazol-3-amine

HRID 571898Notes

Reaction equation

HRID 571898 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([F:18])[CH:17]=1)[CH2:5][C:6]1[CH:7]=[CH:8][C:9](F)=[C:10]([CH:13]=1)[C:11]#[N:12].O.[NH2:20][NH2:21]>C(O)CCC.O.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([F:18])[CH:17]=1)[CH2:5][C:6]1[CH:13]=[C:10]2[C:9](=[CH:8][CH:7]=1)[NH:21][N:20]=[C:11]2[NH2:12]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 441342595-(3,5-Difluorobenzyl)-2-fluorobenzonitrile

Product 1

HCID 441342655-[(3,5-difluorophenyl)methyl]-1H-indazol-3-amineYield 62%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-(3,5-difluoro-benzyl)-2-fluoro-benzonitrile (20 g, 80.9 mmol) and hydrazine hydrate (19.6 mL, 404 mmol) in n-butanol (200 mL) was heated at 120° C. overnight. The reaction mixture was diluted with water/ethyl acetate and the organic phase washed twice with brine, dried and evaporated. Crude was triturated with diethyl ether and filtered to afford 13 gr of final product. Purification of the resulting organic phase by chromatography over silica gel (DCM/EtOH 95:5) afforded further 6.3 g of the title compound (total amount 19.2 g, 92% yield).

Workup

  1. washthe organic phase washed twice with brine
  2. customdried
  3. customevaporated
  4. customCrude was triturated with diethyl ether
  5. filtrationfiltered

Sources & evidence

ORD record
ord-653c26853bc740debaa494ab5ed294b7
Source dataset
uspto-grants-2015_05
Patent number
US09029356B2

Reaction notes

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