Hydrazine hydrate (1:1) → HCID 22561707, compound

HRID 1839592Notes

Reaction equation

HRID 1839592 reaction equation
O.[NH2:2][NH2:3].F[C:5]1[CH:12]=[CH:11][C:10]([C:13]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:14]=2[CH:15]=[CH:16][NH:17]3)=[CH:9][C:6]=1[C:7]#[N:8]>C(O)CCC>[NH:17]1[C:18]2[C:14](=[C:13]([C:10]3[CH:9]=[C:6]4[C:5](=[CH:12][CH:11]=3)[NH:3][N:2]=[C:7]4[NH2:8])[CH:21]=[CH:20][CH:19]=2)[CH:15]=[CH:16]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 22561837HCID 22561837, compound

Product 1

HCID 22561707HCID 22561707, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Hydrazine hydrate (0.4 mL, 12.7 mmol) was added to a solution of 2-fluoro-5-(1H-indol-4-yl)-benzonitrile (1.2 g, 5.08 mmol) in n-butanol (25 mL). The mixture was heated to reflux under nitrogen for 3 days. The reaction was cooled to room temperature and the solvent was removed. The residue was purified on a silica gel column eluting with DCM:MeOH (95:5) to give 1.05 g (83%) of 5-(1H-indol-4-yl)-1H-indazol-3-ylamine as a white foam.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux under nitrogen for 3 days
  3. customthe solvent was removed
  4. customThe residue was purified on a silica gel column
  5. washeluting with DCM:MeOH (95:5)

Sources & evidence

ORD record
ord-38205ef31e904258b098c9a168398225
Source dataset
uspto-grants-2004_01
Patent number
US06677368B2

Reaction notes

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