Ammonium Chloride → 3-ethyl-1-((2-methoxy-6-methylpyridin-3-yl)methyl)-1H-indazol-4-amine

HRID 79365Notes

Reaction equation

HRID 79365 reaction equation
[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[N+:12]([O-])=O)[N:5]([CH2:15][C:16]2[C:17]([O:23][CH3:24])=[N:18][C:19]([CH3:22])=[CH:20][CH:21]=2)[N:4]=1)[CH3:2].[NH4+].[Cl-]>CCO.O.[Fe]>[CH2:1]([C:3]1[C:11]2[C:10]([NH2:12])=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]([CH2:15][C:16]2[C:17]([O:23][CH3:24])=[N:18][C:19]([CH3:22])=[CH:20][CH:21]=2)[N:4]=1)[CH3:2]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 672600193-ethyl-1-((2-methoxy-6-methylpyridin-3-yl)methyl)-4-nitro-1H-indazole

Product 1

HCID 672595973-ethyl-1-((2-methoxy-6-methylpyridin-3-yl)methyl)-1H-indazol-4-amineYield 63.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

A mixture of 3-ethyl-1-((2-methoxy-6-methylpyridin-3-yl)methyl)-4-nitro-1H-indazole (186 mg, 0.57 mmol), iron powder (318 mg, 5.7 mmol) and NH4Cl (15.2 mg, 0.285 mmol) in EtOH/water (3 mL/0.75 mL) was heated to reflux for 60 minutes. The reaction mixture was filtered through GF/F paper and concentrated to a residue under reduced pressure. Preparative thin layer chromatography eluting with 2% MeOH 0.25% NH4OH in DCM provided the product (108 mg).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 60 minutes
  3. filtrationThe reaction mixture was filtered through GF/F paper
  4. concentrationconcentrated to a residue under reduced pressure
  5. washPreparative thin layer chromatography eluting with 2% MeOH 0.25% NH4OH in DCM

Sources & evidence

ORD record
ord-4cd277522206499c8d71184cfb28c840
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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