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With Oxone; sodium hydrogencarbonate; sodium hydroxide In water; acetone at 8℃; for 0.0833333 h;
3-Nitro-5-methoxycarbonylphenylboronic acid (225 mg, 1.0 mmol) was added to a vigorously stirred solution of sodium hydroxide (59 mg, 1.5 mmol) in water (15 mL), followed by sodium bicarbonate (681 mg, 8.1 mmol) and acetone (1 mL). Oxone.(R). (543 mg, 0.88 mmol) was added slowly, keeping the temperature below 8° C. The reaction mixture was stirred 5 min and quenched with sodium bisulfite (600 mg). The reaction mixture was diluted with ethyl acetate and carefully acidified with concentrated hydrochloric acid. The reaction mixture was extracted with ethyl acetate (3.x.) and the combined organic layers were washed with water and brine and concentrated in vacuo to give 93A (258 mg, 100percent) as a yellow solid. 1H NMR (400 MHz, CD3OD) δ ppm 3.95 (s, 3H) 7.74-7.78 (m, 1H) 7.78-7.83 (m, 1H) 8.23-8.28 (m, 1H); LC/MS 198 (M+H).
With hydrogen;palladium 10% on activated carbon; In ethanol; under 2172.08 Torr; for 0.333333h;
Step 1 3-Amino-5-boronyl-benzoic acid methyl ester <strong>[117342-20-8]3-boronyl-5-nitro-benzoic acid methyl ester</strong> (11.6 g, 51.1 mmol) and 10% Pd/C (1.05 g) were added to 110 mL EtOH in a one liter Parr vessel. The reaction mixture was shaken under 42 psi (2.9 Bar) for 20 minutes. The reaction mixture was purged with nitrogen and filtered through Na2SO4 and Celite. The filtrate was concentrated under reduced pressure to give 9.89 g of 3-amino-5-boronyl-benzoic acid methyl ester.
With potassium phosphate; tri-1-napthylphosphine; water;palladium diacetate; In tetrahydrofuran; at 20℃;Inert atmosphere;
Following a general procedure from Applied Organometallic Chemistry 2004, 18, 602-604, a solution of <strong>[117342-20-8]3-(methoxycarbonyl)-5-nitrophenylboronic acid</strong> (900 mg, 4.0 mmol) in tetrahydrofuran (16 mL) was added to a round bottom flask charged with palladim acetate (27 mg, 0.12 mmol), tri-1-napthylphosphine (112 mg, 0.27 mmol), potassium phosphate (1.70 g, 8.00 mmol), and methyl iodide (0.370 mL, 5.9 mmol) under nitrogen atmosphere. Water (0.14 mL, 7.8 mmol) was added and the mixture was stirred overnight at rt. The reaction mixture was diluted with water and extracted with ethyl acetate (3×). The combined organics were washed with water and brine, dried, and concentrated in vacuo. The residue was purified by silica gel chromatography (gradient from 0 to 40% ethyl acetate in hexanes) to give 89A (0.36 g, 46%) as a white solid. 1H NMR (400 MHz, CDCl3) delta ppm 2.54 (s, 3H) 3.98 (s, 3H) 8.19 (s, 1H) 8.23 (s, 1H) 8.67 (s, 1H).
With Oxone; sodium hydrogencarbonate; sodium hydroxide; In water; acetone; at 8℃; for 0.0833333h;
3-Nitro-5-methoxycarbonylphenylboronic acid (225 mg, 1.0 mmol) was added to a vigorously stirred solution of sodium hydroxide (59 mg, 1.5 mmol) in water (15 mL), followed by sodium bicarbonate (681 mg, 8.1 mmol) and acetone (1 mL). Oxone (543 mg, 0.88 mmol) was added slowly, keeping the temperature below 8 C. The reaction mixture was stirred 5 min and quenched with sodium bisulfite (600 mg). The reaction mixture was diluted with ethyl acetate and carefully acidified with concentrated hydrochloric acid. The reaction mixture was extracted with ethyl acetate (3×) and the combined organic layers were washed with water and brine and concentrated in vacuo to give 93A (258 mg, 100%) as a yellow solid. 1H NMR (400 MHz, CD3OD) delta ppm 3.95 (s, 3H) 7.74-7.78 (m, 1H) 7.78-7.83 (m, 1H) 8.23-8.28 (m, 1H); LC/MS 198 (M+H).
methyl 3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5-nitrobenzoate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
82%
With 1H-imidazole; iron(III) chloride; In water; acetonitrile; at 20℃; for 0.5h;Inert atmosphere;
General procedure: To a solution of aryl boronic acid (1 mmol) in MeCN (4 mL) was added, sequentially, asolution of FeCl3 (8 mg, 0.05 mmol, 5 mol%) in H2O (1 mL), imidazole (204 mg, 3 mmol)and pinacol (118 mg, 1 mmol). The resulting cloudy orange mixture was stirred at roomtemperature for 30 min. The reaction was then diluted with H2O (5 mL) and extracted withEt2O (3 x 8 mL). The combined organic extracts were dried (Na2SO4) and concentrated invacuo. The resulting oil was then purified by a filtration through a silica gel plug (eluting withEt2O), affording the title compound.
(2R,3R,4R,5R,6S)-5-acetamido-2-(acetoxymethyl)-6-(2-bromophenoxy)tetrahydro-2H-pyran-3,4-diyl diacetate[ No CAS ]
(2R,3R,4R,5R,6S)-5-acetamido-2-(acetoxymethyl)-6-((3'-(methoxycarbonyl)-5'-nitro-[1,1'-biphenyl]-2-yl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate[ No CAS ]
With sodium hydrogencarbonate; copper(II) sulfate; In methanol; at 10 - 30℃; for 12h;Inert atmosphere; Sealed tube;
General procedure: Operation steps: Under the condition of argon protection, weigh 0.9mmol boric acid, 0.5mmol reagent, 0.05mmol copper sulfate, 0.75mmol sodium bicarbonate,5 mL of methanol was placed in a 25 mL sealed tube and reacted at room temperature for 12 h. After the reaction is over,Add 10 mL of water, extract with anhydrous ether, and dry over anhydrous magnesium sulfate.Filtered through celite, concentrated, and the residue was subjected to flash silica gel column chromatography.125 mg of a colorless oily liquid was obtained with a yield of 89%.
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