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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2177072Generated: October 31, 2026

Dimethylformamide → HCID 57471190, compound

https://huagongshe.com/reaction/2177072

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
Reactant7-(Tert-butoxycarbonylamino)-8-(4-chlorobenzyl)-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonateHCID 57467204—
CatalystZinc cyanide (Zn(CN)2)HCID 11186—
CatalystFerrocene-1,1'-bis-(diphenylphosphine)HCID 635956—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
ProductHCID 57471190HCID 57471190—

Reaction Conditions

Temperature90 °C

Reaction Steps

DPPF (8.1 mg, 0.015 mmol) and Pd2 dba3 (3.35 mg, 0.00365 mmol) were suspended in dimethylformamide (0.4 mL) and after stirring at room temperature under an inert atmosphere of nitrogen for 20 min 7-[(tert-butoxycarbonyl)amino]-8-(4-chlorobenzyl)-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate (38 mg, 0.073 mmol) and zinc cyanide (12.87 mg, 0.110 mmol) were added. The reaction mixture was stirred at 90° C. for 1 h. The solvent was evaporated in vacuo. Water (10 mL) was added to the crude product and the aqueous layer was extracted with ethyl acetate (two times with 10 mL). The combined organic extracts were dried (Na2SO4) and concentrated in vacuo. The crude product was purified by flash chromatography (dichloromethane, silica gel). Yield: 16 mg (0.040 mmol, 55%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09067871B2
Source datasetuspto-grants-2015_06
ORD IDord-7a8dfac9dc6148149b60aa4711b624e4
Source noteuspto-grants-2015_06