| 71% |
With potassium phosphate;dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; In tetrahydrofuran; toluene; at 110℃; for 8h;Inert atmosphere; |
Example 6Synthesis of compound XX-8[0103][Chem. 15] [0104] In a 50-mL reaction container, XX-4 (177.05 mg,0.50 mmol) and 2-isopropoxy-6-methoxyphenylboronic acid (420 mg, 2.0 mmol) were mixed in a toluene/tetrahydrofuran (6 mL/3 mL) mixture solvent, and dissolved oxygen was removed by nitrogen. Then, Pd(OAc)2 (2.3 mg, 0.01 mmol), 2- dicyclohexylphosphino-2 ' , 6 ' -dimethoxybiphenyl (S-Phos) (10.3 mg, 0.025 mmol), and tripotassium phosphate (575.7 mg, 2.5 mmol) were added to the mixture under a nitrogen atmosphere, followed by heating to reflux at 110C for 8 hours. The reaction solution was cooled to room temperature,concentrated under reduced pressure, and subjected to silica gel chromatography (mobile phase: hexane/chloroform = 1/2) for isolation and purification to obtain XX-8 (187 mg, yield: 71%) as a white solid powder.[0105] Mass-spectrometry (MS) and nuclear magnetic resonance spectrometry (NMR) of compound XX-8 gave the results that the molecular weight and the ratio ofintegrated values of NMR peaks well agreed with thestructure of compound XX-8. Specifically, 524 as M+ of this compound was confirmed by matrix-assisted laser desorption- ionization mass spectrometry (MALDI-MS) . The measurement results of nuclear magnetic resonance spectrometry are shown below :XH-NMR (CDCI3) ? (ppm) : 7.72 (s, 2H) , 7.22 (t, 2H) , 6.68 (d, 2H) , 6.65 (d, 2H) , 4.59 (m, 2H), 3.88 (s, 6H) , 1.36 (s, 6H) , 1.35 (s, 6H) .13C-NMR (CDCI3) ? (ppm): 157.98, 156.07, 139.80, 134.87,131.70, 128.52, 122.26, 114.16, 107.54, 104.23, 71.62, 55.98, 22.15. |
| 71% |
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In tetrahydrofuran; toluene; at 110℃; for 8h;Inert atmosphere; |
<Synthesis Example 4: Synthesis of Exemplified Compound A-12>[0137] In a 50-ml reaction vessel, XX-1 (177.05 mg, 0.50 mmol) and 2-isopropoxy-6-methoxyphenylboronic acid (420 mg, 2.0 mmol) were mixed in a toluene/tetrahydrofuran (6 ml/3 ml) mixed solvent. Dissolved oxygen was removed by nitrogen. [0138] Next, Pd(OAc)2 (2.3 mg, 0.01 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (S-Phos) (10.3 mg, 0.025 mmol), and tripotassium phosphate (575.7 mg, 2.5 mmol) were added thereto in a nitrogen atmosphere. The mixture was then heated at 110C to perform a reaction for 8 hours. [0139] The reaction solution was cooled to room temperature and then concentrated under reduced pressure. Separation and purification were performed by silica-gel chromatography (mobile phase: hexane/chloroform = 1/2) to give a white solid power A-12 (187 mg, yield: 71%). Measurement by MALDl-MS demonstrated that M+ of this compound was found to be 524. |
| 71% |
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In tetrahydrofuran; toluene; at 110℃; for 8h;Inert atmosphere; |
In a 50 ml reaction vessel, 177.05 mg (0.50 mmol) of XX-11, 420 mg (2.0 mmol) of 2-isopropoxy-6-methoxyphenylboronic acid: Were mixed in a mixed solvent of toluene / tetrahydrofuran (6 ml / 3 ml), and dissolved oxygen was removed with nitrogen. Next, Pd (OAc) 2: 2.3 mg (0.01 mmol), 2-dicyclohexylphosphino-2 ', 6'- dimethoxybiphenyl (S-Phos): 10.3 mg (0.0 25 mmol) and tripotassium phosphate: 575.7 mg (2.5 mmol) were added in a nitrogen atmosphere, and the mixture was heated under reflux at 110 C. for 8 hours. The reaction solution was cooled to room temperature, concentrated under reduced pressure and separated and purified by silica gel chromatography (mobile phase: hexane / chloroform = 1/2) to obtain D-16 as a white solid powder (187 mg, yield 71% |
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