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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2245935Generated: November 2, 2026

Dimethylformamide → 3-[3-(1-Quinolin-6-ylcyclopropyl) [1,2,4]triazolo[4,3-b][1,2,4]triazin-6-yl]benzonitrile

https://huagongshe.com/reaction/2245935

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
Reactant6-{1-[6-(3-Bromophenyl)[1,2,4]triazolo[4,3-b][1,2,4]triazin-3-yl]cyclopropyl}quinolineHCID 24829629—
CatalystZinc cyanide (Zn(CN)2)HCID 11186—
CatalystZincHCID 23994—
CatalystHCID 178418851HCID 178418851—
Product3-[3-(1-Quinolin-6-ylcyclopropyl) [1,2,4]triazolo[4,3-b][1,2,4]triazin-6-yl]benzonitrileHCID 24829631—

Reaction Conditions

Temperature170 °C

Reaction Steps

A mixture of 6-{1-[6-(3-bromophenyl)[1,2,4]triazolo[4,3-b][1,2,4]triazin-3-yl]cyclopropyl}quinoline (Example 40, 10 mg, 0.02 mmol), zinc cyanide (3.24 mg, 0.0271 mmol), bis(tri-t-butylphosphine)palladium (7 mg, 0.01 mmol), and zinc powder (1.77 mg, 0.0271 mmol) in DMF (0.6 mL) was heated at 170° C. for 20 min under microwave. After cooling to ambient temperature, the mixture was filtered. The filtrate was diluted with methanol and subject to preparative RP-HPLC (pH=10) to afford the desired product. Analytical LCMS: (M+H)+=390.2.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07683060B2
Source datasetuspto-grants-2010_03
ORD IDord-6c0b35b6e81648fd87628b848daacb5c
Source noteuspto-grants-2010_03