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4'-[1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylethynyl]-4-(6-hydroxy-3-oxo-3H-xanthen-9-yl)-biphenyl-3-carboxylic acid[ No CAS ]
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-((trimethylsilyl)ethynyl)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With potassium carbonate;palladium dichloride; In water; acetone; at 20℃; for 10h;
EXAMPLE XV 1-Chloro-4-(beta-D-glucopyranos-1-yl)-2-(4-ethynyl-benzyl)-benzene To a solution of 3.25 g 1-chloro-4-(2,3,4,6-tetra-O-acetyl-D-glucopyranos-1-yl)-2-bromomethyl-benzene, 1.46 g <strong>[630127-51-4]4-trimethylsilylethynyl-phenylboronic acid</strong> and 2.10 potassium carbonate in 45 mL acetone and 15 mL water under argon is added 32 mg palladium dichloride. The reaction mixture is stirred for 10 h at ambient temperature and then diluted with brine. The resultant mixture is extracted with ethyl acetate, the combined extracts are dried over sodium sulfate, and the solvent is removed in vacuo. The residue is taken up in 40 mL methanol, and 8 mL of 4 M aqueous potassium hydroxide solution are added. The solution is stirred at ambient temperature for 1 h and then neutralized with 1 M hydrochloric acid. The methanol is evaporated, and the residue is diluted with brine and extracted with ethyl acetate. The organic extracts collected are dried over sodium sulfate, and the solvent is removed. The residue is chromatographed on silica gel (dichloromethane/methanol 1:0?6:1). Yield: 1.37 g (58% of theory) Mass spectrum (ESI+): m/z=406/408 (Cl) [M+H]+ 1-Chloro-4-(2,3,4,6-tetra-O-benzoyl-D-glucopyranos-1-yl)-2-bromomethyl-benzene can be employed for the reaction described above as well.
2-[(2S,4S)-4-methylpyrrolidin-2-yl]-5-[2-[4-[2-[(2S,4S)-4-methylpyrrolidin-2-yl]-1H-imidazol-4-yl]phenyl]ethynyl]-1H-benzimidazole hydrochloride[ No CAS ]
With sodium hydrogencarbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In water; isopropyl alcohol; at 85℃;sealed tube;
To a solution of tert-butyl (2S,4S)-2-(4-iodo-1 H-imidazol-2-yl)-4-methyl- pyrrolidine-1 -carboxylate (150 mg, 0.3976 mmol) and ([4- (2- trimethylsilylethynyl)phenyl]boronic acid (130 mg, 0.6 mmol) in isopropanol (3 mL) are added sequentially Pd(DPPF)(Cl)2.CH2Cl2 (16 mg, 0.02 mmol), and 2 M NaHC03 (600 uL, 1.2 mmol). The mixture is heated to 85 C in a sealed tube overnight. After reaction, the solvent is removed under reduced pressure and the residue is purified by flash column chromatography on silica gel using methanol/CH2Cl2 0-5% to provide tert-butyl (2S,4S)-4-methyl-2-[4-[4-(2- trimethylsilylethynyl)phenyl]-1 H-imidazol-2-yl]pyrrolidine-1 -carboxylate (168 mg, 95%).LC/MS: m/z = 423.98 (M+H+).