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CAS No. : | 149817-62-9 | MDL No. : | MFCD06796965 |
Formula : | C15H10BrN3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CJRRILXBSCRHKN-UHFFFAOYSA-N |
M.W : | 312.16 | Pubchem ID : | 10614995 |
Synonyms : |
|
Num. heavy atoms : | 19 |
Num. arom. heavy atoms : | 18 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 78.4 |
TPSA : | 38.67 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.32 cm/s |
Log Po/w (iLOGP) : | 2.99 |
Log Po/w (XLOGP3) : | 2.65 |
Log Po/w (WLOGP) : | 3.97 |
Log Po/w (MLOGP) : | 1.8 |
Log Po/w (SILICOS-IT) : | 4.12 |
Consensus Log Po/w : | 3.11 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.01 |
Solubility : | 0.0302 mg/ml ; 0.0000968 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -3.11 |
Solubility : | 0.241 mg/ml ; 0.000771 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -7.15 |
Solubility : | 0.0000222 mg/ml ; 0.000000071 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.57 |
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 |
---|---|---|
86% | Stage #1: at 100℃; for 12 h; Stage #2: With potassium carbonate In water |
Example 5 4'-Bromo-2,2';6',2"-terpyridine (5) A 500 mL flask was charged with 2,6-bis-pyridyl-4-(1H)-pyridone (2.47 g, 9.9 mmol), phosphorus pentabromide (6.6 g, 15.4 mmol), and phosphorus oxybromide (30 g) and heated to 100° C. with stirring for 12 h, giving a black oily residue. The reaction was cooled to room temperature; ice was added cautiously to the reaction until the evolution of gas subsided. The reaction mixture was neutralized with K2CO3 (aq), extracted with CH2Cl2 (3*300 mL), dried over MgSO4, and filtered. Removal of solvent gave a tan colored solid which was purified by column chromatography on neutral alumina using 2:1 CH2Cl2:hexanes as the eluant, providing 2.65 g of pure 4'-bromo-2,2';6',2"-terpyridine (86percent yield, based on 2.47 g of the 2,6-bis-pyridyl-4-(1H)-pyridone starting material). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With hydrogen bromide; dihydrogen peroxide In methanol; water at 20℃; for 20 h; | A stirred solution of terpyridine (3.0 g, 0.013 mmol) and HBr (1.04 g, 0.7 mL, 0.013 mmol) in CH3OH (60 mL) was added to a 47percent aqueous solution of H2O2 (0.44 g, 0.4 mL, 0.013 mmol) slowly, over a period of 15 min at room temperature. The mixture was stirred for 20 h whilst monitoring the reaction progress by TLC. After completion, the solvent was removed under reduced pressure and the residue dissolved in EtOAc (150 mL), washed with brine (3 .x. 100 mL) and dried over anhydrous Na2SO4. The product was isolated by careful column chromatography on silica gel using CH2Cl2-EtOAc (4:1, v/v, 200 mL) to give a yellow-red viscous liquid which was allowed to air dry, and finally recrystallized from Et2O-EtOH to afford the title compound 1 (2.74 g, 91percent) as a bright yellow solid. Found: C, 57.94; H, 3.54; N, 13.27; C15H10N3Br requires C, 57.71; H, 3.23; N, 13.46; mp 209-211 °C; IR (KBr): 3475, 3407, 3039, 2806, 1606, 1583, 1562, 1524, 1454, 1442, 1423, 1355, 1289, 1172, 1153, 1078, 1039, 991, 857, 833, 784, 764, 547 cm-1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | Example 5 4'-Bromo-2,2';6',2"-terpyridine (5) A 500 mL flask was charged with 2,6-bis-pyridyl-4-(1H)-pyridone (2.47 g, 9.9 mmol), phosphorus pentabromide (6.6 g, 15.4 mmol), and phosphorus oxybromide (30 g) and heated to 100 C. with stirring for 12 h, giving a black oily residue. The reaction was cooled to room temperature; ice was added cautiously to the reaction until the evolution of gas subsided. The reaction mixture was neutralized with K2CO3 (aq), extracted with CH2Cl2 (3*300 mL), dried over MgSO4, and filtered. Removal of solvent gave a tan colored solid which was purified by column chromatography on neutral alumina using 2:1 CH2Cl2:hexanes as the eluant, providing 2.65 g of pure 4'-bromo-2,2';6',2"-terpyridine (86% yield, based on 2.47 g of the 2,6-bis-pyridyl-4-(1H)-pyridone starting material). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With copper(l) iodide; diisopropylamine;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 70℃; for 2h; | [5-Ethynyl-10,20-di(2',6'-bis(3,3-dimethylbutoxy)phenyl)porphinato]zinc(II) (155 mg, 0.16 mmol), 4'-bromo-2,2';6',2-terpyridine (280 mg, 0.90 mmol), diisopropylamine (8 mL), and THF (30 mL) were brought together in an oven-dried 100 mL Schlenk tube. The solution was degassed via three freeze-pump-thaw cycles following which Pd(PPh3)4 (30 mg, 0.026 mmol) and CuI (8 mg, 0.042 mmol) were added. The reaction was stirred under N2 at 70 C. for 20 h, cooled to room temperature, and evaporated. The product was purified by column chromatography on neutral alumina using 3:2 hexanes:THF as the eluant. The product eluted as a green band; the volatiles were evaporated and the residual solid was further purified on a size exclusion column (SX-1 biobeads) utilizing a THF eluant. A second round of chromatography on neutral alumina using 1:1 THF:hexanes as the eluant, gave 126 mg of pure compound 21 (67% yield, based on 155 mg of the [5-ethynyl-10,20-di(2',6'-bis(3,3-dimethylbutoxy)phenyl)porphinato]zinc(II) starting material). 1H-NMR (250 MHz, pyridine-d5) 10.14 (s, 1 H), 10.08 (d, 2 H, J=4.5 Hz), 9.36 (d, 2 H, J=4.6 Hz), 9.34 (d, 2 H, J=4.5 Hz), 9.31 (s, 2 H), 9.36 (d, 2 H, J=4.4 Hz), 8.89 (m, 4 H), 8.06 (t, 2 H, J=8.3 Hz), 7.94 (dt, 2 H, J=7.7 Hz, 1.9 Hz), 7.38 (m, 6 H), 4.13 (t, 8 H, J=7.1 Hz), 0.93 (t, 8 H, J=7.5 Hz), 0.33 (s, 36 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With copper(l) iodide; diisopropylamine;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 70℃; for 20h; | [5,15-Diethynyl-10,20-di(2',6'-bis(3,3-dimethylbutoxy)phenyl)porphinato]zinc(II) (123 mg, 0.13 mmol), 4'-bromo-2,2';6',2-terpyridine (330 mg, 1.06 mmol), diisopropylamine (8 mL), and THF (30 mL) were brought together in an oven-dried 100 mL Schlenk tube. The solution was degassed via three freeze-pump-thaw cycles following which Pd(PPh3)4 (30 mg, 0.026 mmol) and CuI (10 mg, 0.053 mmol) were added. The reaction was stirred under N2 at 70 C. for 20 h, cooled to room temperature, and evaporated. The product was purified by column chromatography on neutral alumina using 7:3 hexanes:THF as the eluant. The product eluted as a purplish green band; the volatiles were evaporated and the residual solid was further purified on a size exclusion column (SX-1 biobeads) utilizing a THF eluant. A second round of chromatography on neutral alumina using 3:2 hexanes:THF as the eluant, gave 97 mg of pure compound 22 (52% yield, based on 123 mg of the [5,15-diethynyl-10,20-di(2',6'-bis(3,3-dimethylbutoxy)phenyl)porphinato]zinc(II) starting material). 1H-NMR (250 MHz, pyridine-d5) 10.01 (d, 4 H, J=4.5 Hz), 9.30 (s, 4 H), 9.25 (d, 4 H, J=4.5 Hz), 8.90 (8 H, m), 8.08 (t, 2 H, J=8.3 Hz), 7.94 (dt, 4 H, J=7.7 Hz, 1.9 Hz), 7.40 (8 H, m), 4.18 (t, 8 H, J=7.5 Hz), 0.99 (t, 8 H, J=7.5 Hz), 0.36 (s, 36 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | Example 6 [Ruthenium(II) (2,2';6',2"-Terpyridyl)(4'-bromo-2,2';6',2"-terpyridyl)](PF6)2 (6) A 500 mL flask was charged with Ru(tpy)Cl3 (2.20 g, 5 mmol), 4'-bromo-2,2';6',2"-terpyridine (1.62 g, 5.2 mmol), methanol (500 mL) and N-ethyl-morpholine (1 mL), refluxed for 2 h, and then cooled to room temperature. The solvent volume was reduced by 75%, following which it was diluted with an equal volume of aqueous ammonium hexafluorophosphate. The product precipitated as a red solid. This material was filtered, washed successively with water and ether, and dried to give 4.03 g of product (86% yield, based on 2.20 g of the Ru(tpy)Cl3 starting material). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | Example 9 [Osmium(II) (2,2';6',2"-Terpyridyl)(4'-bromo-2,2';6',2"-terpyridyl)](PF6)2 (9) Os(tpy)Cl3 (1.06 g, 2.0 mmol) and 4'-bromo-2,2';6',2"-terpyridine (655 mg, 2.1 mmol) were refluxed in ethylene glycol (50 mL) for 1 h. The reaction mixture was cooled to room temperature and diluted with 50 mL of water. The solid precipitate was filtered, washed successively with water and ether, and dried. This brownish black solid was dissolved in a minimal amount of acetonitrile, and purified by column chromatography on silica using 80:18:2 MeCN:water:sat. KNO3 as the eluant. The tree fractions collected corresponded to the compounds generated by ligand scrambling [bis-(2,2';6',2"-terpyridine)Os(II), bis-(4'-bromo-2,2';6',2"-terpyridine)Os(II), and the desired product]. The second band corresponded to the product; the volume of misfraction was reduced to 50 mL, and ammonium hexafluorophosphate (1 g) in 10 mL of water was added, yielding a brown precipitate. This material was filtered, washed successively with water and ether, and dried, giving 860 mg of product (42% based on 1.06 g of the Os(tpy)Cl3 starting material). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With hydrogen bromide; dihydrogen peroxide; In methanol; water; at 20℃; for 20h; | A stirred solution of terpyridine (3.0 g, 0.013 mmol) and HBr (1.04 g, 0.7 mL, 0.013 mmol) in CH3OH (60 mL) was added to a 47% aqueous solution of H2O2 (0.44 g, 0.4 mL, 0.013 mmol) slowly, over a period of 15 min at room temperature. The mixture was stirred for 20 h whilst monitoring the reaction progress by TLC. After completion, the solvent was removed under reduced pressure and the residue dissolved in EtOAc (150 mL), washed with brine (3 × 100 mL) and dried over anhydrous Na2SO4. The product was isolated by careful column chromatography on silica gel using CH2Cl2-EtOAc (4:1, v/v, 200 mL) to give a yellow-red viscous liquid which was allowed to air dry, and finally recrystallized from Et2O-EtOH to afford the title compound 1 (2.74 g, 91%) as a bright yellow solid. Found: C, 57.94; H, 3.54; N, 13.27; C15H10N3Br requires C, 57.71; H, 3.23; N, 13.46; mp 209-211 C; IR (KBr): 3475, 3407, 3039, 2806, 1606, 1583, 1562, 1524, 1454, 1442, 1423, 1355, 1289, 1172, 1153, 1078, 1039, 991, 857, 833, 784, 764, 547 cm-1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With 10% palladium on activated charcoal; triethylamine; In dichloromethane; benzene; at 110 - 120℃; for 8h;Darkness; | A mixture of 4-bromoterpyridine (1) (1.00 g, 3.20 mmol) and 9,10-dibromoanthracene (1.08 g, 3.20 mmol) was dissolved in C6H6-CH2Cl2 (1:1, v/v, 160 mL), and the solution stirred for 10 min until all the solid had dissolved. Next, Et3N (1.0 mL) and Pd/C (0.045 g) were added. After heating for 8 h at reflux, the mixture was concentrated under reduced pressure and distilled H2O (30 mL) was added. The organic material was extracted with CHCl3 (100 mL) and evaporated to dryness. The solid was recrystallized from EtOH to afford the title compound L1 as a pink-red solid (yield = 1.36 g, 65%, mp 189-190 C). IR (KBr): 3419, 3048, 2925, 2852, 1744, 1620, 1581, 1562, 1453, 1437, 1423, 1304, 1256, 1078, 1039, 1028, 989, 926, 832, 763, 747, 675, 578. UV-vis (lambdamax nm, epsilon, 104 M-1 cm-1, CHCl3): 342 (3.6900); 361 (7.7000); 381 (12.4000); 403 (11.6000). 1H NMR (CDCl3): delta 8.69 (d, J = 4.4 Hz, 2H, H-3, 3), 8.60 (d, J = 8.0 Hz, 2H, H-5, 5), 8.56 (dd, J = 3.2, 6.7 Hz, 4H, anthr.), 8.44 (d, J = 7.8 Hz, 1H, H-3'), 7.94 (t, J = 7.8 Hz, 2H, H-4, 4), 7.84 (t, J = 7.7 Hz, 2H, H-6, 6), 7.60 (dd, J = 3.1, 6.8 Hz, 4H, anthr.), 7.27 (t, J = 4.4 Hz, 1H, H-5'). 13C NMR (CDCl3): delta 156.26, 155.36, 149.14, 137.89, 136.83, 131.06, 128.28, 127.45, 123.73, 123.53, 121.16, 120.99. Found: C, 71.10; H, 3.83; N, 8.48, C29H18N3Br requires, C, 71.32; H, 3.71; N, 8.60. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In toluene; for 69h;Inert atmosphere; Reflux; | In a stream of argon, 100.0 mg of 4,6-bis(3-biphenylyl)-2-[3,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl)phenyl]-1,3,5-triazine, 105 mg of <strong>[149817-62-9]4'-bromo-2,2':6',2"-terpyridine</strong> and 12.9 mg of tetrakis (triphenylphosphine) palladium were suspended in a mixed solvent comprised of 1 mL of an aqueous 2M sodium carbonate solution and 3 mL of toluene, and the obtained mixture was distilled under reflux for 69 hours. The resultant reaction mixture was cooled to room temperature, and then distilled under a reduced pressure to remove all volatile materials. Water was added to the concentrate, and the thus-deposited solid was collected by filtration and washed with methanol. The thus-obtained crude product was purified by alumina chromatography using chloroform as an eluent to give 110 mg of the target 4,6-bis(3-biphenylyl)-2-[3,5-bis(2,2':6',2"-terpyridin-4'-yl)phenyl]-1,3,5-triazine as a white solid (yield: 85%). 1H-NMR(CDCl3):delta7.26-7.32(m,10H),7.61(t,J=7.7Hz,2H),7.69 (brdd,J=7.9,1.5Hz,4H),7.79(brd,J=7.4Hz,2H),7.85(ddd,J=7.6,7.6,1.8 Hz,4H),8.48(t,J=1.7Hz,1H),8.64(ddd,J=4.7,1.8,0.8Hz,4H),8.68(brdt, J=7.9,1.0Hz,4H),8.77(brdt,J=6.5,1.6Hz,2H),8.90(s,4H),9.03(t,J=1.6 Hz,2H),9.26(d,J=1.7Hz,2H) 13C-NMR(CDCl3):delta119.5(CH×4),121.4(CH×4),123.9(CHx4),127.3 (CH×4),127.5(CH×2),127.9(CH×2),128.2(CH×2),128.6(CH×2),128.9(CH× 4),129.2(CH×2),130.3(CH),131.4(CH×2),136.6(quart.×2),136.9(CH×4), 137.8(quart.),140.3(quart.×2),140.7(quart.×2),141.6(quart.×2), 149.3(CH×4),149.9(quart.×2),156.2(quart.×4),156.2(quart.×4),171.3 (quart.),171.9(quart.×2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In toluene; for 45h;Inert atmosphere; Reflux; | In a stream of argon, 1.00 g of 2- [3,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl)phenyl]-4,6-diphenyl-1,3,5-trizine, 1.33 g of <strong>[149817-62-9]4'-bromo-2,2':6',2"-terpyridine</strong> and 165 mg of tetrakis(triphenylphosphine)palladium were suspended in a mixed solvent comprised of 20 mL of an aqueous 2M sodium carbonate solution and 50 mL of toluene, and the obtained mixture was distilled under reflux for 45 hours. The resultant reaction mixture was cooled to room temperature, and then distilled under a reduced pressure to remove all volatile materials. Water was added to the concentrate, and the thus-deposited solid was collected by filtration and washed with methanol. The thus-obtained crude product was purified by alumina chromatography using a hexane/chloroform (1:1-0:1) mixed solvent as an eluent to give 1.20 g of the target 2-[3,5-bis(2,2':6',2"-terpyridin-4'-yl)phenyl]-4,6-diphenyl-1,3,5 -triazine as a white solid (yield: 88%). 1H-NMR(CDCl3):delta7.29-7.34(m,4H),7.52-7.55(m,6H),7.85(ddd,J= 7.8,7.8,1.8Hz,4H),8.46(t,J=1.6Hz,1H),8.66-8.69(m,8H),8.77-8.80(m, 4H),8.87(s,4H),9.21(d,J=1.6Hz,2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In toluene; for 59h;Inert atmosphere; Reflux; | In a stream of argon, 100.0 mg of 2-[3,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborora-2-yl)phenyl]-4,6-di(2-naphthyl)-1,3,-5-triazine, 133 mg of <strong>[149817-62-9]4'-bromo-2,2':6',2"-terpyridine</strong> and 14.0 mg of tetrakis (triphenylphosphine) palladium were suspended in suspended in a mixed solvent comprised of 1 mL of an aqueous 2M sodium carbonate solution and 4 mL of toluene, and the obtained mixture was distilled under reflux for 59 hours. The resultant reaction mixture was cooled to room temperature, and then distilled under a reduced pressure to remove all volatile materials. Water was added to the concentrate, and the thus-deposited solid was collected by filtration and washed with methanol. The thus-obtained crude product was purified by alumina chromatography using a hexane/chloroform (1:2-0:1) mixed solvent as an eluent to give 91.0 mg of the target 2-[3,5-bis(2,2':6',2"-terpyridin-4'-yl)phenyl]-4,6-di(2-naphthyl) -1,3,5-triazine as a white solid (yield: 69%). 1H-NMR(CDCl3):delta7.31(ddd,J=7.6,4.8,1.2Hz,4H),7.47-7.55(m, 4H),7.85(ddd,J=7.6,7.6,1.8Hz,4H),7.85-7.87(m,2H),7.97(d,J=8.5Hz, 2H),8.07(d,J=7.7Hz,2H),8.48(t,J=1.7Hz,1H),8.66-8.71(m,8H),8.85 (dd,J=8.5,1.7Hz,2H),8.92(s,4H),9.30(d,J=1.7Hz,2H),9.39(brs,2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In toluene; for 69h;Inert atmosphere; Reflux; | In a stream of argon, 100.0 mg of 4,6-bis(4-biphenylyl)-2-[3,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl)phenyl]-1,3,5-triazine, 105 mg of <strong>[149817-62-9]4'-bromo-2,2':6',2"-terpyridine</strong> and 12.9 mg of tetrakis (triphenylphosphine) palladium were suspended in a mixed solvent comprised of 1 mL of an aqueous 2M sodium carbonate solution and 3 mL of toluene, and the obtained mixture was distilled under reflux for 69 hours. The resultant reaction mixture was cooled to room temperature, and then distilled under a reduced pressure to remove all volatile materials. Water was added to the concentrate, and the thus-deposited solid was collected by filtration and washed with methanol. The thus-obtained crude product was purified by alumina chromatography using chloroform as an eluent to give 110 mg of the target 4,6-bis(4-biphenylyl)-2- [3,5-bis(2,2':6',2"-terpyridin-4'-yl)phenyl] -1,3,5-triazine as a white solid (yield: 62%). 1H-NMR(CDCl3):delta7.29-7.36(m,6H)7.43(t,J=7.7Hz,4H)7.65(brd, J=7.7Hz,4H),7.76(d,J=8.5Hz,4H),7.85(ddd,J=7.6,7.6,1.8Hz,4H),8.44 (t,J=1.7Hz,1H),8.67-8.71(m,8H),8.85-8.88(m,4H),8.88(s,4H),9.24(d, J=1.7Hz,2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In toluene; for 86h;Inert atmosphere; Reflux; | In a stream of argon, 100.0 mg of 2-[3,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl)phenyl]-4,6-diphenylpyrimidine, 167 mg of <strong>[149817-62-9]4'-bromo-2,2':6',2"-terpyridine</strong> and 20.6 mg of tetrakis(triphenylphosphine)palladium were suspended in a mixed solvent comprised of 0.8 mL of an aqueous 2M sodium carbonate solution and 5 mL of toluene, and the obtained mixture was distilled under reflux for 86 hours. The resultant reaction mixture was left to stand to room temperature, and then distilled under a reduced pressure to remove all volatile materials. Methanol was added to the concentrate, and the thus-deposited solid was collected by filtration and washed with water and methanol. The thus-obtained crude product was purified by silica gel chromatography using a hexane/chloroform (1:4) mixed solvent as an eluent to give 129 mg of the target 2-[3,5-bis(2,2':6',2"-terpyridin-4'-yl)-phenyl]-4,6-diphenylpyrimidine as a white solid (yield: 94%). 1H-NMR(CDCl3):delta7.30(dd,J=7.5,2.4,1.2Hz,4H),7.48-7.54(m,6H), 7.84(dd,J=8.0,7.9,1.9Hz,4H),8.05(s,1H),8.30(dd,J=7.9,1.6Hz,4H), 8.35(t,J=1.7Hz,1H),8.65-8.69(m,8H),8.86(s,4H),9.16(d,J=1.7Hz,2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In toluene; for 66h;Inert atmosphere; Reflux; | In a stream of argon, 70.0 mg of 4,6-bis(4-tert-butylphenyl) - 2-[3,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl)phenyl]-1,3,5-triazine, 78.0 mg of 4'-bromo-2,2":6',2"-terpyridine and 9.6 mg of tetrakis (triphenylphosphine) palladium were suspended in a mixed solvent comprised of 1 mL of an aqueous 2M sodium carbonate solution and 2 mL of toluene, and the obtained mixture was distilled under reflux for 66 hours. The resultant reaction mixture was cooled to room temperature, and then methanol was added to the reaction mixture. The thus-deposited solid was collected by filtration, and the obtained crude product was purified by alumina chromatography using chloroform as an eluent to give 49.0 mg of the target 4,6-bis(4-tert-butylphenyl)-2-[3,5-bis(2,2':6',2"-terpyridin-4'-yl)phenyl]-1,3,5-triazine as a white solid (yield: 53%) . 1H-NMR(CDCl3):delta1.30(s,18H),7.26(ddd,J=7.7,4.2,1.1Hz,4H), 7.49(d,J=8.5Hz,4H),7.80(ddd,J=7.7,7.7,1.7Hz,4H),8.37(t,J=1.7Hz, 1H),8.62-8.66(m,12H),8.83(s,4H),9.15(d,J=1.7Hz,2H). 13C-NMR(CDCl3):delta31.3(CH3×6),35.2(quart.×2),119.6(CH×4), 121.5 (CH×4),123.9(CH×4),125.7(CH×4),128.4(CH×2),129.1(CH×4),130.3(CH), 133.5(quart.×2),136.9(CH×4),138.3(quart.),140.4(quart.×2),149.2 (CH×4),150.1(quart.×2),156.1(quart.×6),156.2(quart.×4),171.2 (quart.),171.8(quart.×2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88.5% | With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate; In tetrahydrofuran; at 80℃; for 5h;Inert atmosphere; | (1) In a 250 mL three-necked flask, nitrogen gas was introduced and 0.02 mol of the intermediate was added.4'-Bromo-2,2':6',2'-terpyridine is dissolved in 100 ml of tetrahydrofuran (THF).Then add 0.024 mol of bis (pinacol) diboron,0.0002 mol (1,1'-bis(diphenylphosphino)ferrocene)dichloropalladium(II) and0.05 mol of potassium acetate was added, the mixture was stirred, and the mixed solution of the above reactants was heated under reflux at a reaction temperature of 80 C for 5 hours; after the reaction was completed, 100 ml of water was added thereto, and the mixture was filtered and dried in a vacuum oven. The obtained residue was separated and purified on silica gel column to afford Intermediate D2; HPLC purity 99.8%, yield 88.5%. |
74% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In toluene; for 24h; | Sub 2-1-6 (6.24g, 20mmol) was dissolved in the toluene afterthat bis-pinacolato diboron (5.58g, 22mmol), Pd(dppf)Cl2 catalyst (0.44g, 0.6mmol), KOAc (5.89g, 60mmol ) a borate compound sequence synthesized by stirring for 24 hours after the addition, as, after the thus obtained compound was separated over a silicagel column and recrystallized to give 5.32g of Sub 2 (6) (yield: 74%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With tetrakis(triphenylphosphine) palladium(0); water; potassium carbonate; In toluene; at 90 - 100℃; for 36h;Inert atmosphere; | Under a nitrogen atmosphere, 2,2'-fluorene diboronate spiro (1.137g, 2mmol), 4'- bromo-2,2 ': 6', 2 "- three-bromopyridine (1.374g, 4.4mmol ), An aqueous potassium carbonate solution (80 mL, 0.1 mol / L) and toluene (200 mL), and finally the catalyst Pd (PPh3) 4 (300 mg, 0.26 mmol) was added and the reaction was allowed to proceed to 90-100 C for 36 hours, The organic phase was collected and dried to give the crude product which was purified by silica gel column chromatography eluting with ethyl acetate: V hexane = 1: 20 to give a white solid, which was the target compound C01 Of crude. The crude product was further sublimed and purified by chemical vapor deposition system at a temperature of 320 . The yield of C01 was 82%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In toluene; at 90 - 100℃; for 36h;Inert atmosphere; | Under nitrogen, into 2,7-spiro fluorene boronate (1.257g, 2.2mmol), 4'- bromo-2,2 ': 6', 2 "- three-bromopyridine (1.520g, 4.8mmol (300 mL, 0.26 mmol) of Pd (PPh3) 4 (300 mg, 0.26 mmol) was added and the temperature was raised to 90-100 C for 36 hours, and 50 mL of toluene was added thereto. The organic phase was collected and dried to give a crude product, which was purified by silica gel column chromatography eluting with a mixture of V1,2-dichloroethane: V-hexane = 1: 25 to give a white solid As the crude of the target compound C21. The crude product was further sublimed and purified by chemical vapor deposition system at a temperature of 315 . The yield of C21 was 86%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With propylamine; tetrakis(triphenylphosphine) palladium(0); at 80℃; for 24h;Inert atmosphere; Sealed tube; | A mixture of 13 (315 mg, 1.01 mmol), 16 (205 mg, 1.01 mmol)and Pd(PPh3)4 (96 mg, 8 mol%) in a pressure tube was suspendedin n-propylamine (10 mL) and degassed with N2 for 15 min. Thetube was sealed and heated at 80 C for 24 h. By this time a brownprecipitate had formed, which was collected and washed withwater (20 mL), EtOH (20 mL) and Et2O (5 mL) before drying undervacuum to provide 5 as a brown solid (230 mg, 81%): mp 202-208 C; 1H NMR (500 MHz, CDCl3) d 9.32 (d, 1H, J = 3.4 Hz), 9.27(d, 1H, J = 2.3 Hz), 8.99 (d, 1H, J = 7.4 Hz), 8.80 (m, 4H), 8.72 (d,1H, J = 8.0 Hz), 8.33 (d, 1H, J = 8.6 Hz), 8.22 (s, 2H), 7.98 (m, 2H),7.86 (m, 1H), 7.73 (dd, 1H, J = 8.0, 4.6 Hz), 7.45 (m, 2H); 13C NMR(125 MHz, DMSO-d6) d 156.1, 154.7, 151.9, 151.3, 150.0, 146.3,145.8, 138.2, 137.1, 134.9, 133.6, 132.6, 128.3, 127.9, 125.5,124.7, 124.5, 122.7, 121.5, 118.2, 93.0, 90.8. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With propylamine; tetrakis(triphenylphosphine) palladium(0); at 80℃; for 18h;Inert atmosphere; Sealed tube; | A mixture of 13 (165 mg, 0.53 mmol), 19 (161 mg, 0.53 mmol)and Pd(PPh3)4 (31 mg, 5 mol%) in a pressure tube was suspendedin n-propylamine (10 mL) and degassed with N2 for 15 min. Thetube was sealed and heated at 80 C for 18 h. By this time a brownprecipitate had formed, which was collected and washed withEtOH (20 mL) and Et2O (5 mL) before drying under vacuum to provide8 as a yellow solid (230 mg, 81%): mp 244-248 C; 1H NMR(500 MHz, CDCl3) d 9.25 (d, 1H, J = 4.0 Hz), 9.21 (d, 1H, J = 4.6 Hz),8.83 (d, 1H, J = 8.0 Hz), 8.73 (d, 2H, J = 4.6 Hz), 8.61 (m, 3H), 8.26(d, 1H, J = 8.0 Hz), 8.13 (s, 2H), 7.89 (m, 2H), 7.76 (m, 1H), 7.65(m, 6H), 7.37 (m, 2H); 13C NMR (125 MHz, CDCl3) d 155.7, 151.1,150.8, 149.3, 146.3, 146.0, 137.1, 135.9, 134.8, 133.1, 132.2,132.0, 131.9, 131.8, 131.8, 131.0, 128.3, 128.1, 124.2, 123.6,123.5, 123.3, 123.1, 122.8, 121.3, 119.7, 95.0, 93.2, 89.8, 88.1. |
Tags: 149817-62-9 synthesis path| 149817-62-9 SDS| 149817-62-9 COA| 149817-62-9 purity| 149817-62-9 application| 149817-62-9 NMR| 149817-62-9 COA| 149817-62-9 structure
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