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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1029216Generated: October 27, 2026

1-Ethynyl-2-(trifluoromethyl)benzene → 1-{[2-(trifluoromethyl)phenyl]ethynyl}benzo[c]-1,8-naphthyridin-6(5H)-one

https://huagongshe.com/reaction/1029216

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1-Ethynyl-2-(trifluoromethyl)benzeneHCID 4100856—
Reactant1-Chlorobenzo[C][1,8]naphthyridin-6(5H)-oneHCID 58168008—
Product1-{[2-(trifluoromethyl)phenyl]ethynyl}benzo[c]-1,8-naphthyridin-6(5H)-oneHCID 5816807812%

Reaction Steps

The title compound was synthesized according to the procedure described for the preparation of Example 160 using 83 (100 mg, 0.43 mmol) and 2-ethynyl-α,α,α-trifluorotoluene (0.09 mL, 0.65 mmol) to provide 254 (18 mg, 12% yield) as a tan solid. LC-MS (M+H=365 obsd.=365). 1H NMR (400 MHz, d6-DMSO): δ 9.62 (d, 1H), 8.50 (d, 1H), 8.41 (dd, 1H), 8.08 (d, 1H), 7.95 (d, 1H), 7.86 (m, 2H), 7.74 (m, 2H), 7.39 (d, 1H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08735584B2
Source datasetuspto-grants-2014_05
ORD IDord-b6f8606aafa24ac484c5b8217660dcb9
Source noteuspto-grants-2014_05