Nitrogen → 1-(4-Fluorophenyl)-1h-indazol-5-amine

HRID 218162Notes

Reaction equation

HRID 218162 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.N[C@@H]1CCCC[C@H]1N.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[F:27][C:28]1[CH:33]=[CH:32][C:31](I)=[CH:30][CH:29]=1.N#N>O1CCOCC1.[Cu]I>[F:27][C:28]1[CH:33]=[CH:32][C:31]([N:7]2[C:8]3[C:4](=[CH:3][C:2]([NH2:1])=[CH:10][CH:9]=3)[CH:5]=[N:6]2)=[CH:30][CH:29]=1

Participants

8

Reactant 5

HCID 947NitrogenHCID 96054-FluoroiodobenzeneHCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 880121H-Indazol-5-amine

Product 1

HCID 592357271-(4-Fluorophenyl)-1h-indazol-5-amineYield 1,090.4%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Procedure

Commercially available 5-aminoindazole (15 g, 113 mmol) was dissolved in 100 mL dry dioxane in a stainless steel pressure bottle followed by the addition of trans-1,2-diaminocyclohexane (6.4 g, 56 mmol), CuI (2.1 g, 11.3 mmol), K3PO4 (43 g, 203 mmol), and 1-fluoro-4-iodobenzene (27.5 g, 11.3 mmol). The reactor was sealed and heated at 120 C for 72 h under a blanket of N2. The reaction was filtered through a large SiO2 plug on a fitted funnel using EtOAc until the eluent ran clear (˜1 L). The solution was concentrated in vacuo and the dark brown solid was taken up in hot EtOAc (˜150 mL) and hexane was added to induce precipitation. The dark black solid was filtered and dried under vacuum to give 28 g (73%) of pure N1-(4-fluorophenyl)-5-aminoindazole. MS found: (M+H)+=228.

Workup

  1. customThe reactor was sealed
  2. filtrationThe reaction was filtered through a large SiO2 plug on a fitted funnel
  3. concentrationThe solution was concentrated in vacuo
  4. additionhexane was added
  5. customprecipitation
  6. filtrationThe dark black solid was filtered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-5915d7d6f29240e29f83736f394fc4a3
Source dataset
uspto-grants-2012_06
Patent number
US08198311B2

Reaction notes

Loading…