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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 388979Generated: October 29, 2026

Acetic Acid → 4-[5-(1H-indazol-6-yl)-1H-imidazol-2-yl]-2-nitrophenylamine

https://huagongshe.com/reaction/388979

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AcidHCID 176—
ReactantDimethylformamideHCID 6228—
ReactantBenzoic acid, 4-amino-3-nitro-HCID 74115—
ReactantDiisopropylethylamineHCID 81531—
Reactant2-bromo-1-(1H-indazol-6-yl)ethan-1-oneHCID 86615223—
SolventWaterHCID 962—
Product4-[5-(1H-indazol-6-yl)-1H-imidazol-2-yl]-2-nitrophenylamineHCID 68446337—

Reaction Steps

DIEA (0.7 mL, 3.6 mmol) was added to a solution of 2-bromo-1-(1H-indazol-6-yl)ethanone (3 mmol) and 4-amino-3-nitrobenzoic acid (0.643 g, 3.5 mmol) in DMF (10 mL) and the solution was stirred at room temperature for 2 h. NH4OAc (5 g, 65 mmol) was added to the solution, followed by HOAc (10 mL) and the mixture was stirred at 140° C. for 2 h. The mixture was cooled to room temperature and poured into H2O (30 mL). The precipitate was collected by filtration, washed with H2O (10 mL) and dried under reduced pressure to afford 4-[5-(1H-indazol-6-yl)-1H-imidazol-2-yl]-2-nitrophenylamine (0.56 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08377983B2
Source datasetuspto-grants-2013_02
ORD IDord-3555a85afa3447a5ad64a01d82625d58
Source noteuspto-grants-2013_02