Ammonium Chloride → 1-((5-(trifluoromethyl)pyridin-2-yl)methyl)-1H-indazol-4-amine

HRID 706695Notes

Reaction equation

I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-])=O)[N:4]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][N:16]=2)[N:3]=1.[NH4+].[Cl-]>CO.[Zn]>[F:24][C:21]([F:22])([F:23])[C:18]1[CH:19]=[CH:20][C:15]([CH2:14][N:4]2[C:5]3[CH:6]=[CH:7][CH:8]=[C:9]([NH2:11])[C:10]=3[CH:2]=[N:3]2)=[N:16][CH:17]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3-iodo-4-nitro-1-((5-(trifluoromethyl)pyridin-2-yl)methyl)-1H-indazole (0.464 g, 1.04 mmol) in MeOH (10 mL) at 0° C. was added Zn dust (0.339 g, 5.18 mmol) followed by saturated aqueous NH4Cl (10 mL). The mixture was stirred at 0° C. for 1 hour, then warmed to ambient temperature and stirred for an additional 1 hour. The mixture was diluted with MeOH and filtered. Saturated aqueous NH4OAc was added to the filtrate and the mixture was concentrated to remove bulk MeOH. The mixture was extracted with EtOAc, and the combined organic extracts were washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4, filtered and concentrated. The product was purified by column chromatography (25 to 100% EtOAc/hexane) to afford 0.230 g (76%) of the product as yellow/orange oil.

Workup

temperaturewarmed to ambient temperature
stirringstirred for an additional 1 hour
filtrationfiltered
additionSaturated aqueous NH4OAc was added to the filtrate
concentrationthe mixture was concentrated
customto remove bulk MeOH
extractionThe mixture was extracted with EtOAc
washthe combined organic extracts were washed with saturated aqueous NaHCO3 and brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe product was purified by column chromatography (25 to 100% EtOAc/hexane)

Sources & evidence

ORD record: ord-dfbafa3d922949cebc6297b5de7242ad
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174981B2

Reaction notes

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