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HazMat fee for 500 gram (Estimated)
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Structure of 2567-29-5 * Storage: {[proInfo.prStorage]}
* 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.
With carbon tetrabromide; triphenylphosphine In dichloromethane at 20℃; for 1.5 h;
Carbon tetrabromide (8.99 g, 27.1 MMOL) and triphenyl phosphine (7.11 g, 27.1 MMOL) were added to a stirred solution of biphenyl-4-yl methanol (5.00 g, 27.1 MMOL) in dichloromethane (100 mL) at room temperature. Stirring was continued at room temperature for 1.5 hours then the solvent removed by evaporation under reduced pressure. The residue was purified by column chromatography on silica gel (1: 20 diethyl ether: cyclohexane) to give the title compound (6.37g, 95percent) as a white solid.'H NMR (400 MHz: CDCI3) : 7.6 (4 H), 7.45 (4 H), 7.35 (1 H), 4.55 (2 H).
95%
With carbon tetrabromide; triphenylphosphine In dichloromethane at 20℃; for 1.5 h;
Carbon tetrabromide (8.99 g, 27.1 mmol) and triphenyl phosphine (7.11 g, 27.1 mmol) wereadded to a stirred solution of biphenyl-4-yl methanol (5.00 g, 27.1 mmol) indichloromethane (100 ml_) at room temperature. Stirring was continued at room temperaturefor 1.5 hours then the solvent removed by evaporation under reduced pressure. Theresidue was purified by column chromatography on silica gel (1:20 diethyl ether:cyclohexane) to give the title compound (6.37g, 95percent) as a white solid. 1H NMR (400 MHz:CDCI3): 7.6 (4 H), 7.45 (4 H), 7.35 (1 H), 4.55 (2 H).
91%
With phosphorus pentoxide; potassium bromide In acetonitrile at 20℃; for 1 h;
General procedure: To a mixture of alcohol (1 mmol) and KBr (1.5 mmol, 0.18 g) in acetonitrile (5 mL), P2O5 (1.5 mmol, 0.23 g) was added and the reaction was stirred at room temperature for the time specified in Table 3. After reaction completion (TLC or GC), the reaction mixture was filtered and the residue washed with ethyl acetate (3 × 8 mL). The combined organic layers were washed with water (10 mL) and dried over Na2SO4. The solvent was removed under reduced pressure to afford the corresponding product. If necessary, further purification was performed by column chromatography.
75%
With phosphorus tribromide In chloroform; di-isopropyl ether
Reference Example 50 4-Phenylbenzyl Bromide To a solution of 4-phenylbenzyl alcohol (1.00 g, 5.43 mmol) in a mixture of diisopropyl ether (10 mL) and chloroform (20 mL) was added phosphorus tribromide (0.98 g, 3.62 mmol) with ice-cooling and the mixture was stirred at room temperature for 1 hour. This reaction mixture was diluted with water and extracted with diisopropyl ether. The organic layer was washed with water and saturated aqueous sodium hydrogen carbonate solution, dried over MgSO4, and filtered. The filtrate was concentrated under reduced pressure and the residue was recrystallized from ethanol-hexane to provide 1.00 g of the title compound. Yield 75percent. m.p. 86-88° C. 1H-NMR (CDCl3) δ: 4.55 (2H, s), 7.32-7.67 (9H, m).
Reference：
[1] Organic Letters, 2013, vol. 15, # 9, p. 2210 - 2213
[2] Patent: WO2005/26120, 2005, A1, . Location in patent: Page/Page column 21
[3] Patent: WO2004/110974, 2004, A1, . Location in patent: Page 22
[4] Organic Letters, 2012, vol. 14, # 21, p. 5428 - 5431,4
[5] Organic Letters, 2018, vol. 20, # 10, p. 3061 - 3064
[6] Tetrahedron Letters, 2016, vol. 57, # 2, p. 168 - 171
[7] Recueil des Travaux Chimiques des Pays-Bas, 1993, vol. 112, # 10, p. 535 - 548
[8] Tetrahedron Asymmetry, 1993, vol. 4, # 9, p. 2025 - 2026
[9] Organic Letters, 2012, vol. 14, # 11, p. 2754 - 2757
[10] Tetrahedron Letters, 2001, vol. 42, # 32, p. 5571 - 5573
[11] Patent: US6248766, 2001, B1,
[12] Carbohydrate Research, 1982, vol. 105, p. 168 - 172
[13] Mendeleev Communications, 2007, vol. 17, # 2, p. 82 - 84
[14] Helvetica Chimica Acta, 1952, vol. 35, p. 1348,1351
[15] Journal of Organic Chemistry, 1961, vol. 26, p. 2662 - 2667
[16] Journal of Organic Chemistry, 1980, vol. 45, # 25, p. 5177 - 5183
[17] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1991, # 12, p. 2067 - 2080
[18] Journal of Medicinal Chemistry, 1989, vol. 32, # 8, p. 1757 - 1763
[19] Tetrahedron, 2002, vol. 58, # 17, p. 3361 - 3370
[20] European Journal of Medicinal Chemistry, 2005, vol. 40, # 6, p. 563 - 581
[21] Journal of the American Chemical Society, 2001, vol. 123, # 51, p. 12832 - 12836
[22] Patent: WO2006/90235, 2006, A1, . Location in patent: Page/Page column 46
[23] Patent: US6399629, 2002, B1,
[24] Patent: US2008/194565, 2008, A1, . Location in patent: Page/Page column 17
[25] Patent: US2003/225158, 2003, A1, . Location in patent: Page 22-23
[26] Organic Letters, 2013, vol. 15, # 22, p. 5818 - 5821
2
[ 589-15-1 ]
[ 98-80-6 ]
[ 2567-29-5 ]
Yield
Reaction Conditions
Operation in experiment
82.4%
With sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 100℃;
To a dry 250 mL three-necked flask was added phenylboronic acid (2.44 g, 0.02 mol), p-bromobenzyl bromide (4.99 g, 0.02 mol), tetrakis(triphenylphosphine)palladium (0.23 g, 0.2 mmol).Add anhydrous potassium carbonate (8.28 g, 0.06 mol), and 50 mL of toluene, 30 mL of absolute ethanol,10 mL of deionized water was further added with sodium borohydride (0.57 g, 15 mmol), and the mixture was heated to 100 ° C in an oil bath. After the reaction was confirmed by thin-plate chromatography, silica gel column chromatography was performed with ethyl acetate and n-hexane system to collect the product, 4.07. g, yield 82.4percent.
73%
With C24H20Cl2NPPdS; potassium carbonate; palladium In toluene at 100℃; for 24 h;
General procedure: A 100 ml round bottom flask was fitted with a reflux condenser and a magnetic stirrer bar. The flask was charged with toluene (15 ml) and the appropriate amount of catalyst reagents and the internal standard (n-Decane: 2.59 mmol). The contents were thoroughly mixed and an initial sample (t0) was then taken. The reaction flask was placed in an oil bath at the desired temperature and the reaction mixture allowed to heat/reflux with stirring. A sample was taken and analyzed every 10 min for the first hour and every 30 min thereafter until t3h. In cases where conversionwas not complete after 3 h, the reaction mixturewas then allowed to stir for a total of 24 h. The reaction at 140 °C was performed in a sealed tube. All catalytic reactions were done under aerobic conditions. Percentage conversions were determined by GC with n-decane as the internal standard and the coupling products were characterized by mass spectrometry (Table 4) as well as 1H NMR spectroscopy (Entry 5, Table 4 only).
Reference：
[1] Tetrahedron Letters, 2004, vol. 45, # 37, p. 6959 - 6962
[2] Patent: CN107522643, 2017, A, . Location in patent: Paragraph 0101-0103; 0107; 0108
[3] Journal of Organometallic Chemistry, 2012, vol. 703, p. 34 - 42
3
[ 644-08-6 ]
[ 2567-29-5 ]
Reference：
[1] Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1994, vol. 241, p. 159 - 166
[2] Synlett, 2013, vol. 24, # 12, p. 1549 - 1554
[3] Journal of the American Chemical Society, 1955, vol. 77, p. 5354,5356[4] Chemische Berichte, 1956, vol. 89, p. 925,929
[5] Phosphorus, Sulfur and Silicon and the Related Elements, 1990, vol. 53, # 1-4, p. 43 - 67
[6] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 21, p. 2735 - 2740
[7] European Journal of Organic Chemistry, 2009, # 36, p. 6328 - 6335
[8] Journal of Medicinal Chemistry, 2012, vol. 55, # 9, p. 4407 - 4424
[9] European Journal of Medicinal Chemistry, 2013, vol. 61, p. 26 - 40
[10] Organic Letters, 2013, vol. 15, # 16, p. 4194 - 4197
[11] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 23, p. 6492 - 6499
[12] European Journal of Organic Chemistry, 2014, vol. 2014, # 16, p. 3402 - 3410
((1,1'-biphenyl-4-yl)methyl)triphenylphosphonium bromide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
In para-xylene; at 120℃; for 6h;Inert atmosphere;
General procedure: A dried Schlenk tube was charged with 2 (0.2 mmol), Ph3P (63 mg, 0.24 mmol) and p-xylene (2 mL) under N2. The resulting mixture was stirred at 120 C for 6 h. After being cooled to room temperature, tBuOK (40 mg, 0.36 mmol) and p-xylene (0.5 mL) were added into the mixture under N2 and stirred at room temperature for 15 min. PDFA (143 mg, 0.4 mmol) and p-xylene (0.5 mL) were added into the solution under N2 and stirred at 100 C for another 1 h. After being cooled to room temperature, the mixture was subjected to flash column chromatography to afford the pure product.
2-(biphenyl-4-ylmethyl)-7-isobutyl-5-methyl-3-(phenylamino)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
38%
With potassium carbonate; In acetone; at 20℃;
A mixture of 7-isobutyl-5-methyl-lH-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (12.0 g, 0.0383 mmol), /?-biphenylmethyl bromide (9.46 mg, 0.0383 mmol) and potassium carbonate (5.3 mg, 0.0383 mmol) in acetone (2.5 mL) is stirred at room temperature overnight. The solvent is evaporated under reduced pressure. The residue is directly purified by chromatography to give 7.0 mg product as white solids (Yield: 38.0%). 1H NMR (400 MHz, CDCl3) delta 0.97 (s, 3H), 0.99 (s, 3H), 2.33 (m, IH). 3.34 (s, 3H), 3.85 (d, 2H), 4.99 (s, 2H), 6.76 (s, IH), 6.91-7.56 (m, 13H). MS (FAB) m/z 480.3 [M+H]+.
1,3-thiazol-5-ylmethyl 1,1'-biphenyl-4-ylmethyl[3-{(1,1'-biphenyl-4-ylmethyl)[(1,3-thiazol-5-ylmethoxy)carbonyl]amino}propyl]carbamate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
25%
With sodium hydride; In N,N-dimethyl-formamide; at 20℃; for 18h;
[00388] Example 65. Preparation of 1,3-thiazol-5-ylmethyI l,l'-biphenyl-4-ylmethyl(3-{(l,l'- biphenyl-4-ylmethylJKl.S-thiazol-S-ylmethoxyJcarbonylJaminoJpropyOcarbamate [00389] Following the same procedure as in Example 62, using the compound of Example 61 (30 mg, 0.08 mmol), sodium hydride (8 mg, 0.19 mmol) and 4-phenyIbenzyl bromide (46 mg, 0.19 mmol), gave 14.6 mg, 25% of the title compound. NMR (CDC13) delta ppm 8.76 (s, 2 H) 7.87 (s, 2 H) 7.03 - 7.65 (m, 18 H) 5.36 (s, 4 H) 4.25 - 4.56 (m, 4 H) 3.03 - 3.40 (m, 4 H) 1.61 (s, 2 H); MS (M H- H+) = 689. [00382] Example 62. Preparation of 1,3-thiazol-5-ylmethyl 4-benzoylbenzyl(3-{(4-benzoylbenzyl)[(1,3-thiazol-5-ylmethoxy)carbonyl]amino}propyl)carbamate[00383] To a solution of the compound of Example 61 (35 mg, 0.10 mmol) in DMF (1 mL) was added 4-(bromomethyl)benzophenone (62 mg, 0.23 mmol). Sodium hydride (10 mg, 0.24 mmol) was added and the solution stirred at room temperature for 18 hours, after which time was poured into 1:1EtOAc:lN HCl (10 mL). The layers were separated and the organic layer was washed with IN HCl (1 x5 mL) and brine (1 x 5 mL), dried over Na2SCi, filtered and the solvent removed in vacuo to leave a crude residue that was purified by column chromatography on silica gel (1-2% CH3OH/CH2CI2) to give 11 mg, 15% of the title compound.
tert-butyl 1,1'-biphenyl-4-ylmethyl(3-{(1,1'-biphenyl-4-ylmethyl)[(1,3-thiazol-5-ylmethoxy)carbonyl]amino}propyl)carbamate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
48%
With sodium hydride; In N,N-dimethyl-formamide; at 20℃; for 18h;
[00408] Example 75. Preparation of tert-butyl l,l'-biphenyl-4-ylmethyI(3-{(l,r-biphenyI-4-yl methyl) [(1,3-thiazol-5-ylmethoxy)carbonyl]amino}propyl)carbamate; [00409] Following the same procedure as in Example 62, using the compound of Example 69 (64 mg, 0.20 mmol), sodium hydride (18 mg, 0.45 mmol) and 4-phenylbenzyl bromide (111 mg, 0.45 mmol) gave 63 mg, 48% of the title compound. NMR (CDC13) delta ppm 8.76 (s, 1 H) 7.87 (s, 1 H) 7.10 - 7.67 (m, 18 H) 5.37 (s, 2 H) 4.24 - 4.55 (m, 4 H) 3.02 - 3.37 (m, 4 H) 1.60 - 1.88 (m, 2 H) 1.44 (s, 9 H); MS (M + H+) = 648. [00382] Example 62. Preparation of 1,3-thiazol-5-ylmethyl 4-benzoylbenzyl(3-{(4-benzoylbenzyl)[(1,3-thiazol-5-ylmethoxy)carbonyl]amino}propyl)carbamate; [00383] To a solution of the compound of Example 61 (35 mg, 0.10 mmol) in DMF (1 mL) was added 4-(bromomethyl)benzophenone (62 mg, 0.23 mmol). Sodium hydride (10 mg, 0.24 mmol) was added and the solution stirred at room temperature for 18 hours, after which time was poured into 1:1EtOAc:lN HCl (10 mL). The layers were separated and the organic layer was washed with IN HCl (1 x5 mL) and brine (1 x 5 mL), dried over Na2SCi, filtered and the solvent removed in vacuo to leave a crude residue that was purified by column chromatography on silica gel (1-2% CH3OH/CH2CI2) to give 11 mg, 15% of the title compound. NMR (CD3OD) delta ppm 8.91 - 9.06 (m, 2 H) 7.15 - 8.00 (m, 20 H)5.43(s, 2 H) 5.38 (s, 2 H) 4.36 - 4.64 (m, 4 H) 3.1 1 - 3.44 (m, 4 H) 1.61 - 1.86 (m, 2 H); MS (M + H+) =745.
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