Hydrazine → 3-(4-Fluorophenyl)-1H-indazole-5-carbonitrile

HRID 1349610Notes

Reaction equation

HRID 1349610 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][C:3]=1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)=O.O.[NH2:20][NH2:21].NN>O>[F:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[C:3]3[C:2](=[CH:7][CH:6]=[C:5]([C:8]#[N:9])[CH:4]=3)[NH:21][N:20]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 9321HydrazineHCID 24654Hydrazine hydrate (1:1)HCID 224801564-Fluoro-3-(4-fluorobenzoyl)benzonitrile

Product 1

HCID 222606703-(4-Fluorophenyl)-1H-indazole-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a flask containing 4-fluoro-3-{(4-fluorophenyl)carbonyl}benzenecarbonitrile (4.2 g, 0.017 mmol) was added hydrazine monohydrate (15 mL) and anhydrous hydrazine (10 mL). In an addition flask the procedure was repeated. Both flasks were allowed to stir overnight exposed to the atmosphere. LCMS confirmed the reactions were complete. To the flasks were added an excess amount of water. The reactions were allowed to stir for two hours. The product of the reactions was collected via a flitted funnel by filtration and combined to yield the title compound. The product was allowed to dry under vacuum and taken on crude into the next step of the synthesis. 1H NMR (DMSO-d6) 8.7 (s, 1H), 8.1 (m, 2H), 7.7–7.8 (m, 2H), 7.3–7.4 (t, 2H), ES-MS m/z 238 [M+1]+

Workup

  1. customIn an addition flask the procedure was repeated
  2. customBoth flasks were allowed
  3. stirringto stir for two hours
  4. filtrationThe product of the reactions was collected via a flitted funnel by filtration

Sources & evidence

ORD record
ord-d5a66066385349f79c59a3a7af76b545
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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