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CAS No. : | 189178-09-4 | MDL No. : | MFCD09030768 |
Formula : | C24H15N | Boiling Point : | - |
Linear Structure Formula : | N(C6H4CCH)3 | InChI Key : | QGICIDGCKPUALM-UHFFFAOYSA-N |
M.W : | 317.38 | Pubchem ID : | 23443705 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
87% | With water; sodium hydroxide; In tetrahydrofuran; at 20℃; for 18h; | In reference to FIG. 2, a third compound according to the present invention, arbitrarily called CL64, was also synthesized, according to diagram 2 below, by a Sonogashira triple coupling between trialkyne 4b (obtained by deprotection of 4a in a basic medium) and 3.5 equivalents of the iodized derivative 5.More specifically, an aqueous solution of NaOH (1 M, 30 mL) is added to a solution of the compound 4a (2.33 g, 4.36 mmol) in THF (30 mL), and the mixture is agitated vigorously at 20 C. for 18 h. After evaporation of the THF, dichloromethane is added. The organic phase is separated, washed with water and dried (Na2SO4). The residue obtained after removal of the solvent is purified by chromatography on a silica column (heptane/CH2Cl2 90:10, then 85:15) to produce 1.20 g (87%) of the compound 4b.The air is purged with a solution of compound 4b (17.9 mg, 0.056 mmol), compound 5 (100 mg, 0.197 mmol) and tri-o-furylphosphine (0.52 mg, 2.26 μmol) in 1.5 mL of toluene/Et3N (5/1) by argon bubbling for 30 min. Then, Pd2 dba3 (0.26 mg, 0.28 μmol) is added, and the mixture is agitated at 20 C. for 20 h. After evaporation of the solvent under reduced pressure, the raw product is purified by chromatography on a silica column (heptane/CH2Cl2 60:40, then 50:50) to produce 19 mg (24%) of CL64. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In flame dried Schlenk flask (100 mL), <strong>[189178-09-4]tris(4-ethynylphenyl)amine</strong> (105.8 mg, 0.33 mmol), Pd(PPh3)4 (62.4mg, 0.054 mol), CuI (3.4mg, 0.018mmol), and anhydrous THF (10 mL) were charged under N2 atmosphere. After 30 min stirring, 4-bromo-1,8-napthalimide (328.9 mg,0.99 mmol) in anhydrous THF (20 mL) and Et3N (6 mL) were added. The mixture was stirred at room temperature overnight. After the starting materials were full reacted, as confirmed by TLC, the mixture was poured to distilled water 50mL. Then, it was extracted by dichloromethane (25 mL × 3). The organic phase dried over Mg2SO4 and evaporated in vacuum. The residue was loaded to the column. Column separation (silica gel 200-300 mesh,eluent: dichloromethane/petroleum = 2/1) produced 286 mg yellow powder (80%).Mp: 281-284C; IR (KBr, υ, cm-1): 780, 1085, 1235, 1274, 1319, 1353, 1503, 1511, 1587,1660, 1697, 2196, 2960. 1H NMR(400 MHz, CDCl3): δ (ppm): 8.73 (3H, d, J = 8.0 Hz), 8.65(3H, d, J = 8.0 Hz), 8.56 (3H, d, J = 8.0 Hz), 7.95 (3H, d, J = 8.0 Hz), 7.84 (3H, t, J = 8.0Hz), 7.64 (6H, d, J = 8.0 Hz), 7.23 (6H, d, J = 8.0 Hz), 4.20 (6H, t, J = 8.0 Hz), 1.73 (6H, m), 1.53-1.44 (6H, m), 0.99 (9H, t, J = 8.0 Hz). 13C NMR (100 MHz, CDCl3): δ (ppm): 164.1,163.9, 147.4, 133.5, 132.4, 131.73, 131.67, 130.7, 130.5, 128.2, 127.7, 127.6, 124.5, 123.2, 122.2,118.1, 117.5, 99.1, 86.8, 40.5, 30.4, 29.8, 20.6, 14.0.Maldi-Tof: [M+H]+ C72H56N4O5 requires1071.412; found [M+H]+ 1071.501; and [M+2H]+ C72H57N4O5 requires 1072.420; found1072.508 (Base). |
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