Hydrazine hydrate (1:1) → 3-pyridin-2-yl-7-(trifluoromethyl)-2H-indazole

HRID 735460Notes

Reaction equation

HRID 735460 reaction equation
F[CH:2]1[CH:7]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=O)[CH:6]=[CH:5][CH:4]=[C:3]1[C:16]([F:19])([F:18])[F:17].O.[NH2:21][NH2:22]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1.[Cl-].[Na+].O.CCOC(C)=O>[N:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:8]1[NH:21][N:22]=[C:2]2[C:7]=1[CH:6]=[CH:5][CH:4]=[C:3]2[C:16]([F:19])([F:18])[F:17]

Participants

7

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67021129(6-Fluoro-5-trifluoromethyl-cyclohexa-2,4-dienyl)-pyridin-2-yl-methanone

Product 1

HCID 670213023-pyridin-2-yl-7-(trifluoromethyl)-2H-indazoleYield 76%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Next, a solution of (6-fluoro-5-trifluoromethyl-cyclohexa-2,4-dienyl)-pyridin-2-yl-methanone (1.5 g, 5.6 mmol), 4-dimethylaminopyridine (0.5 g) and hydrazine hydrate (5 mL) in pyridine (20 mL) was heated at 100° C. overnight. The reaction mixture was cooled and diluted with brine and EtOAc. The organics were washed with water (3×25 mL), then brine (25 mL) and dried over MgSO4. The reaction mixture was concentrated in vacuo and purified by flash chromatography (silica gel 60, EtOAc/CH2Cl2, 19:1) to afford 3-pyridin-2-yl-7-(trifluoromethyl)-2H-indazole as a pale yellow solid (1.1 g, 76%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. washThe organics were washed with water (3×25 mL)
  3. dry with materialbrine (25 mL) and dried over MgSO4
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. custompurified by flash chromatography (silica gel 60, EtOAc/CH2Cl2, 19:1)

Sources & evidence

ORD record
ord-a4ede57a01614b44b13c87c6b270399e
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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