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

HRID 1029216Notes

Reaction equation

HRID 1029216 reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[C:6](=[O:12])[NH:7]2.[C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]([F:28])([F:27])[F:26])#[CH:18]>>[F:26][C:25]([F:27])([F:28])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:17]#[C:18][C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[C:6](=[O:12])[NH:7]2

Participants

3

Reactant 2

HCID 41008561-Ethynyl-2-(trifluoromethyl)benzeneHCID 581680081-Chlorobenzo[C][1,8]naphthyridin-6(5H)-one

Product 1

HCID 581680781-{[2-(trifluoromethyl)phenyl]ethynyl}benzo[c]-1,8-naphthyridin-6(5H)-oneYield 12%

Procedure

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).

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-b6f8606aafa24ac484c5b8217660dcb9
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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