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CAS No. : | 13922-41-3 |
Formula : | C10H9BO2 |
M.W : | 171.99 |
SMILES Code : | C1=CC=C2C(=C1)C(=CC=C2)B(O)O |
MDL No. : | MFCD00019722 |
InChI Key : | HUMMCEUVDBVXTQ-UHFFFAOYSA-N |
Pubchem ID : | 254532 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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 |
---|---|---|
95% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; at 70.0℃;Inert atmosphere; Sealed tube; | General procedure: A bromo-aldehyde (1 mmol), boronic acid (1.1e1.3 mmol), tetrakis(triphenylphosphine)palladium (0.05 mmol), potassium carbonate(3 mmol), water (3 ml), ethanol (4 ml) and toluene (4 ml)were added to a round-bottomed flask. The reaction mixture wasflushed with argon, sealed under septa and heated at 70 C overnight.After cooling to room temperature, water (50 ml) was added,and product was extracted with ethyl acetate (3 x 50 ml). Combinedextracts were washed with brine, dried with anhydrousmagnesium sulfate and evaporated under reduced pressure. Theproduct was purified by column chromatography on silica withchloroform or a mixture of methanol and chloroform (1:9). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Inert atmosphere; | 1-(8-naphthyl)-isoquinoline (8-NAIQ). 1-(8-naphthyl)-isoquinoline was obtained from thereaction of <strong>[63927-22-0]8-bromoisoquinoline</strong> and naphthalene-1-boronic acid by Suzuki coupling [8]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In water; acetonitrile; for 0.166667h;Microwave irradiation; | First, into a recovery flask equipped with a reflux pipe were put 2.05 g of <strong>[38557-72-1]2-chloro-3,5-dimethylpyrazine</strong>, 2.48 g of 1-naphthylboronic acid, 1.53 g of sodium carbonate, 0.066 g of bis(triphenylphosphine)palladium(II)dichloride (abbreviation: Pd(PPh3)2Cl2), 15 mL of water, and 15 mL of acetonitrile, and the air in the flask was replaced with argon. This reaction container was subjected to irradiation with microwaves (2.45 GHz, 100 W) for 10 minutes, whereby heating was performed. After that, water was added to this solution, and an organic layer was extracted with dichloromethane. The obtained organic layer was washed with water and dried with magnesium sulfate. After the drying, the solution was filtered. The solvent of this solution was distilled off, and then the obtained residue was purified by silica gel column chromatography using dichloromethane as a developing solvent. Accordingly, Hdm1npr (a light orange powder, 59% yield), which was the substance to be produced, was obtained. Note that the irradiation with microwaves was performed using a microwaves synthesis system (Discover, produced by CEM Corporation). The synthesis scheme of Step 1 is shown in (a-1) below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In Dimethyl ether; water; at 90℃; for 6h;Inert atmosphere; | (3) Synthesis of 1-(1H-indene-2-yl)naphthalene Finally, 2.7 g (13.8 mmol) of <strong>[10485-09-3]2-bromoindene</strong> was added to a 100 mL Schlenk flask, and dissolved in a mixed solution of 60 mL of DME (dimethyl ether) and 20 mL of water. 3.4 g (18 mmol) of 1-naphthalene boronic acid and 2.8 g (21 mmol) of K2CO3 were added thereto, and argon gas was bubbled therein for 10 min to remove oxygen in the solvent. Thereafter, heating was initiated under an argon gas atmosphere, and when the temperature reached 90 C., 800 mg (0.7 mmol, 5 mol %) of palladium(0)tetrakis(triphenylphosphine) (Pd/C) was added thereto, and stirred for 6 h. Thereafter, the reaction mixture was cooled to room temperature, and 200 mL of water was poured therein to filter resulting brown precipitates, which were washed with about 50 mL of ether and then dried, thereby obtaining 2.4 g (67%) of a white solid. 1H NMR (500 MHz, CDCl3): δ 3.95 (2H, s), 7.20-7.39 (7H, s), 7.82-7.87 (4H, m), 8.00 (1H, s) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); 1-(7-benzofuranyl)-2-di(3,5-di-tert-butyl-4-methoxyphenyl)phosphinenaphthalene; In toluene; at 80℃; for 10h;Glovebox; Inert atmosphere; | In a glove box, 1.0 mmol of a halogenated aromatic or heterocyclic aromatic hydrocarbon compound, 2.0 mmol of 1-naphthylboronic acid, Pd2 (dba) 3, a phosphine ligand and 3.0 mmol of potassium phosphate were charged in 7 mL of anhydrous toluene under nitrogen,After heating to 80 ° C, the reaction was carried out for a period of time. The results are shown in Table 1. The amount of Pd2 (dba) 3 and the phosphine ligand is divided into three types: (1) 0.25 molpercent Pd2 (dba) 3, 0.5 molpercent phosphine ligand, or (2) 0.5 molpercent Pd2 (dba) molpercent phosphine ligand, or (3) 1.0 molpercent Pd2 (dba) 3, 2.0 molpercent phosphine ligand, depending on the amount of ligand used in Table 1. |
81% | With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); C38H31O5P; In toluene; at 80℃; for 8h;Inert atmosphere; Glovebox; | General procedure: In the glove box, Sm5 (0.1 mmol, 1.0 equiv), Sm2 (0.2 mmol, 2.0 equiv), K3PO4 (0.3 mmol, 3.0 equiv), Pd2(dba)3 (1.0percent mmol), (±)-8A (2.0percent mmol) and toluene (4.0mL) were added into a 25 mL single-necked flask, the reaction was stirred at 80 deg. C under nitrogen for 8 hours. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99.3% | Under the protection of argon, 51.6 g (0.2 mol) of 4-bromo-4'-nitrilebiphenyl and 34.4 g (0.2 mol) of 1-naphthaleneboronic acid were used.Potassium carbonate 69.1 g (0.5 mol) and toluene 500 mL were sequentially placed in a reaction flask.After stirring evenly,44.9 mg of palladium acetate and 35.6 mg of tris(m-tolyl)phosphine were added to the reaction flask.The reaction temperature was controlled at 90 C, and the reaction was terminated by HPLC. The reaction was terminated by adding 400 mL of water, and suction filtration was performed.The organic layer was washed with water, dried over anhydrous sodium sulfate and filtered, and then filtered, and then evaporated toluene toluene, toluene, toluene, toluene, toluene, toluene, toluene, toluene, to give a white solid, 57.8 g, yield 99.3% (HPLC), yield 94.6%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75.3% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 100℃; for 24h;Inert atmosphere; | <strong>[1000623-95-9]3,6-bis(5-bromo-2-thienyl)-2,5-bis(2-ethylhexyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione</strong> (150.2mg, 0.22mmol) and 1-naphthyl boronic acid (113.4mg, 0.66mmol) was dissolved in 15mL toluene solution, then add 3mL of ethanol and 2mL aqueous sodium carbonate (sodium carbonate 186.5mg, 1.76mmol), After nitrogen gas was purged for 20 min, tetrakistriphenylphosphine palladium (10.2 mg, 0.0088 mmol) was added, and the mixture was heated to 100 C for 24 hours under nitrogen atmosphere, and then cooled to room temperature. Water and extracted three times with dichloromethane, the extract was dried over anhydrous magnesium sulfate, filtered to obtain the organic solution, the solvent was removed under reduced pressure, chromatographed on silica gel column with petroleum ether/ethyl acetate = 10:1 (v/v) as eluent, to give the crude product, then recrystallized from isopropanol, to obtain the pure black product 129.1mg, yield 75.3% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In toluene;Inert atmosphere; Reflux; | A Straus flask equipped with a stirrer bar was charged with 2-bromopyridine (1.0 equiv.), 1-naphthylboronic acid (1.1 equiv),Pd(PPh3)4 (4 mol%), 2 M aq Na2CO3 (2.5 mL/mmol), toluene(3.8 mL/mmol), and ethanol (1.3 mL/mmol). The mixture wasdegassed by three freeze-pump-thaw cycles and then refluxedunder inert conditions overnight. The mixture was cooled to r.t.and extracted with EtOAc (3 × 20 mL). The organic phases werecombined, dried (MgSO4), and concentrated. The pure ligandwas obtained by flash column chromatography [silica gel,EtOAc-hexane (1:4)].Compound was isolated as viscous liquid that solidified uponstanding. Yield: 1.6 g (99%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.795 g | With potassium carbonate; bis(dibenzylideneacetone)-palladium(0); 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane; In tetrahydrofuran; water; at 75℃; for 18.5h;Sealed tube; | To a solution of 245 <strong>[16657-07-1]7-bromoindene</strong> (3.202 g, 16.42 mmol) and 373 naphthalene-1-boronic acid (3.393 g, 19.73 mmol, 1.20 eq) in 81 tetrahydrofuran (20 mL), 249 potassium carbonate (5.192 g, 37.03 mmol, 2.26 eq) was added. Then a solution of 313 1,3,5,7-tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantane (0.200 g, 0.68 mmol, 0.04 eq) and 314 bis(dibenzylideneacetone)palladium (0.134 g, 0.23 mmol, 0.01 eq) in tetrahydrofuran (20 mL) was added. Then 247 water (8 mL) was added. The reaction vessel was sealed. The reaction was stirred and heated to 75 C. in a sealed vessel for 18.5h. The reaction was allowed to cool to room temperature. The reaction was then concentrated in vacuo. The residue underwent aqueous extraction with pentane (3×50 mL). The combined pentane extracts were washed with saturated, aqueous potassium carbonate (50 mL). The washed pentane extracts were dried with anhydrous magnesium sulfate and filtered. The dried filtrate was concentrated in vacuo. The crude material was purified by silica gel column chromatography with isohexane eluent to give a black solid. The solid was washed with minimal hexane and concentrated under high vacuum to afford the 374 product as a tan solid (2.795 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; at 60℃; for 8h;Inert atmosphere; | Take a 50 mL three-necked flask, put it in the stir bar and the upper reflux tube, fill it with nitrogen, add the raw material S1-126 (2.92 g, 0.01 mol),Raw material S2-126 (1.72 g, 0.01 mol), potassium carbonate (0.012 mol),Tetrakis(triphenylphosphine)palladium (0.5 mmol), toluene (8 mL), water (2 mL),Under the protection of nitrogen, react at 60C for 8 hours, and cool to room temperature after the reaction is complete.Add 3 mL ice water to quench, extract with dichloromethane (3×15 mL),The obtained extract was dried by adding magnesium sulfate, filtered and spin-dried sequentially. The crude product was purified by chromatography (ethyl acetate/n-hexane, 1/10 (volume ratio)) to obtain S3-126 (1.35 g, yield 40%). |