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CAS No. : | 133810-42-1 | MDL No. : | |
Formula : | C14H8N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 204.23 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With (i-Pr)2NH In dichloromethane to a stirred soln. of Pt-complex and diyne in CH2Cl2-i-Pr2NH under N2 was added CuI, the mixt. was stirred at room temp. for 15 h; volatiles were removed under reduced pressure, the residue was dissolvedin CH2Cl2, passed through a short alumina column, evapd., film was wash ed with methanol, pptn. from CH2Cl2-soln. in methanol; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
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57% | A mixture of 52 (389 mg, 2.67 mmol), 4 (100 mg, 1.08 mmol), PdCl2(PPh3)2 (45 mg, 0.06 mmol), and CuI (18 mg, 0.10 mmol) in iPr2NH/THF (25 mL, 1:1.5, v/v) was stirred for 12 h at r.t. under nitrogen. To a solution of the reaction mixture was added Ac2O (3 equiv.), and stirred for 1 h under nitrogen. To the reaction mixture was added powder NaOH (1.37 g, 34.42 mmol), and stirred at 70 C for 1 h.4 The reaction mixture was extracted by EtOAc (50 mL), and washed with water. The organic layer was separated, dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residual material was purified by flash column chromatography on SiO2 (hexane:EtOAc = 3:1, v/v) to afford 1 as a light yellow solid (140 mg, 57 %). 1H NMR (400 MHz, CDCl3, 298 K): delta 8.57 (d, J = 12.0 Hz, 2H), 7.95 (m, 4H), 7.67 (s, 2H), 7.58 (s, 2H), 7.50 (d, J = 12.0 Hz, 2H), 7.43 (d, J = 4.0 Hz, 2H), 1.42 (s, 18H); 13C NMR (100 MHz, CDCl3, 298 K): delta 155.81, 155.62, 153.63, 148.76, 137.59, 128.64, 123.18, 120.29, 119.59, 117.75, 110.76, 105.10, 34.77, 31.85, 29.71. HRMS (ESI) calcd for C34H33N2O2 [M+H]+ 501.2537, found 501.2552. |