Ethanol → Bay-H-1127

HRID 2089242Notes

Reaction equation

HRID 2089242 reaction equation
Cl[C:2]1[C:3]([C:12]#[N:13])=N[C:5]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:7]=1.[NH2:14][NH2:15].O.[CH2:17](O)C>>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:17]=[C:3]2[C:2](=[CH:7][CH:6]=1)[NH:15][N:14]=[C:12]2[NH2:13]

Participants

4

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 67478888HCID 67478888, compound

Product 1

HCID 16736Bay-H-1127

Conditions

Temperature
90 °C

Procedure

Into a 50 mL round-bottom flask, was placed a solution of 3-chloro-6-(trifluoromethyl)picolinonitrile (as prepared in the previous step, 200 mg, 0.97 mmol, 1.00 equiv) in ethanol (15 mL) and NH2NH2.H2O (145 mg, 2.90 mmol, 3.00 equiv). The reaction mixture was stirred overnight at 90° C. The resulting mixture was concentrated under vacuum and purified by silica gel column chromatography with dichloromethane/methanol (100:1) to give 5-(trifluoromethyl)-1H-indazol-3-amine as a yellow solid. LC-MS-(ES, m/z) 203[M+H]

Workup

  1. customInto a 50 mL round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. custompurified by silica gel column chromatography with dichloromethane/methanol (100:1)

Sources & evidence

ORD record
ord-8dc039521abc4dfa8fe2e0ce74eea2f6
Source dataset
uspto-grants-2013_05
Patent number
US08436023B2

Reaction notes

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