Ethanol → 1-benzyl-3-cyclopropyl-1H-indazol-4-amine

HRID 79264Notes

Reaction equation

[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([N+:17]([O-])=O)[CH:13]=[CH:14][CH:15]=2)[C:10]([CH:20]2[CH2:22][CH2:21]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+].C(O)C>[Fe].O>[CH2:1]([N:8]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([NH2:17])[C:11]=2[C:10]([CH:20]2[CH2:21][CH2:22]2)=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a reaction flask was added 1-benzyl-3-cyclopropyl-4-nitro-1H-indazole (60.0 mg, 0.205 mmol), iron powder (114 mg, 2.05 mmol) and ammonium chloride (10.9 mg, 0.205 mmol). Ethanol (0.8 mL) and water (0.2 mL) were added and the mixture was heated at 85° C. with stirring for 60 minutes. The solvent was removed under reduced pressure. Ethyl acetate (0.8 mL) and triethylamine (0.2 mL) was added and the mixture was heated at 60° C. for 10 minutes. The mixture was filtered through glass fiber filter paper, washing with methanol and ethyl acetate. The filtrate was concentrated under reduced pressure. The material was purified by preparative chromatography, eluting with 3% methanol in dichloromethane, containing 0.5% ammonium hydroxide solution to give 1-benzyl-3-cyclopropyl-1H-indazol-4-amine (36 mg).

Workup

customThe solvent was removed under reduced pressure
additionEthyl acetate (0.8 mL) and triethylamine (0.2 mL) was added
temperaturethe mixture was heated at 60° C. for 10 minutes
filtrationThe mixture was filtered through glass fiber
filtrationfilter paper
washwashing with methanol and ethyl acetate
concentrationThe filtrate was concentrated under reduced pressure
customThe material was purified by preparative chromatography
washeluting with 3% methanol in dichloromethane
additioncontaining 0.5% ammonium hydroxide solution

Sources & evidence

ORD record: ord-059cd12138994b049a25a5e13fbb0f92
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841455B2

Reaction notes

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