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CAS No. : | 138008-97-6 | MDL No. : | MFCD03427050 |
Formula : | C9H13BO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XDMKBIIRBDPSOE-UHFFFAOYSA-N |
M.W : | 180.01 | Pubchem ID : | 5084099 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.33 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 52.37 |
TPSA : | 49.69 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.26 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 1.6 |
Log Po/w (WLOGP) : | 0.15 |
Log Po/w (MLOGP) : | 0.65 |
Log Po/w (SILICOS-IT) : | -0.26 |
Consensus Log Po/w : | 0.43 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.11 |
Solubility : | 1.41 mg/ml ; 0.00781 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.26 |
Solubility : | 1.0 mg/ml ; 0.00556 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.85 |
Solubility : | 2.54 mg/ml ; 0.0141 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.96 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
73% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 20℃; for 21h;Heating / reflux; | Add tetrakis (triphenylphosphine) palladium (0) (500 mg) to a degassed suspension of H-IMIDAZOLE (5.0 g, 34 mmol) and 2-isopropoxyphenyl boronic acid (9.19 g, 51 mmol) in dioxane (250 mL) and 2 M sodium carbonate solution (10.81 g, 102 mmol) at room temperature under nitrogen and heat the mixture at reflux for 21 hours. Remove the solvent under reduced pressure, dilute the residue with ethyl acetate (500 mL) and filter through a plug of Celite. Dry the filtrate over sodium sulfate, treat with silica gel (20 g) and remove the solvent under reduced pressure. Purify the residue by flash column chromatography on silica gel, eluting with ethyl acetate, to afford crude 4- (2- ISOPROPOXYPHENYL)-1H-IMIDAZOLE (5.01 g, 73%) which is used without further purification in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 90℃; for 12h; | A solution of benzoic acid N'-[2-(2-bromo-4-fluoro-phenoxy)-acetyl]-N'-isopropyl-hydrazide (50 mg, 0.122 mmol) in DME (3 ml)/2M Na2CO3 (0.215 ml, 0.427 mmol) was treated with 2-isopropoxylphenylboronic acid (32 mg, 0.183 mmol) and Pd[PPh3]4 (27 mg, 0.0244 mmol) for 12 hours at 90 C. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated. The crude was purified first on a silica gel column with 30% ethyl acetate/hexanes then by RP HPLC to afford the product as a white solid (22 mg, 38%). MS m/e 465.27 (M+H+) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With sodium hydrogencarbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; water; for 8h;Heating / reflux; | c. Synthesis of 4-chloro-6-(2-isopropoxyphenyl)-pyrimidine.; To a solution of 4,6-dichloropyrimidine (0.207 g, 1.38 mmol) and 2- isopropoxyphenylboronic acid (0.18 g, 1.0 mmol) in mixture of dimethoxyethane (4 ml_) and water (0.6 ml_) were added NaHCO3 (0.231 g, 2.76 mmol) and (PPh3^PdCI2 (0.029 g) and the reaction mixture was refluxed for 8 h, then was evaporated. The residue was dissolved in CH2CI2 (10 ml_) and washed with water, dried over anhydrous K2CO3 and evaporated. The crude product was isolated by column chromatography on silica (eluent CH2CI2) as oil. Yield of 4-chloro-6-(2-isopropoxyphenyl)-pyhmidine 0.18 g (72%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | With sodium carbonate;palladium diacetate; triphenylphosphine; In 1,4-dioxane; water; at 110℃; for 1h;Heating / reflux; | To a stirred mixture of 4-(6-chloro-pyrimidin-4-ylcarbamoyl)-piperidine-1 -carboxylic acid benzyl ester (VIII) (0.830 g, 2.22 mmol), <strong>[138008-97-6]2-isopropyloxyphenylboronic acid</strong> (0.400 g, 2.22 mmol) in saturated sodium carbonate solution (10 ml) and 1 ,4-dioxane (10 ml) was added palladium(ll) acetate (0.1 g, 0.44 mmol) followed by triphenylphosphine (0.11 g, 0.42 mmol) at room temperature under an atmosphere of nitrogen. The resulting mixture was heated to reflux at 110C for one hour and monitored by TLC. The reaction mixture was filtered through a celite bed and the filtrate was extracted with ethyl acetate (3 x 100 ml). The organic layers were separated, combined, dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by flash column chromatography (silica gel, elution with 50% ethyl acetate/n-hexanes) to afford 4-[6-(2-isopropoxy-phenyl)-pyhmidin-4-ylcarbamoyl]-piperidine-1 -carboxylic acid benzyl ester (XIII) (0.36 g, 37%) as a white solid. HPLC purity lambda = 220 nm: 98%. ESMS: m/z = 448 (M+1 ). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50.5% | Example 104 N-[(6-hydr oxy-2-{2-[(1-methylethyl)oxy]phenyl}-5-quinoxalinyl)carbonyl]glycine To a mixture of the compound from example 5(a) (0.300 g, 0.85 mmol), <strong>[138008-97-6]2-isopropoxyphenylboronic acid</strong> (0.183 g, 1.02 mmol) and potassium carbonate (0.234 g, 1.69 mmol) in 1,4-dioxane (3.0 mL) and water (1.0 mL) was added tetrakis(triphenylphosphine)palladium (0.010 g, 8.47 mumol) followed by evacuation of the reaction vessel and purging with nitrogen. The reaction mixture was heated in a Biotage Initiator microwave synthesizer at 120 C. for 30 min to get the intermediate ester and upon cooling, tetrahydrofuran (5.0 mL) and 1N aqueous sodium hydroxide (8.0 mL) were added. After stirring for 15 min at ambient temperature, the mixture was quenched with 1N aqueous hydrochloric acid and the resulting precipitate was filtered, purified via rp-HPLC (acetonitrile/water+0.1% trifluoroacetic acid) to the title compound (0.163 g, 50.5% yield) as a yellow solid. 1H NMR (300 MHz, DMSO-d6) delta ppm 15.23 (s, 1H, br), 12.90 (s, 1H, br), 11.41 (t, 1H, J=6.0 Hz), 9.39 (s, 1H), 7.88 (m, 1H), 7.52 (m, 2H), 7.27 (d, 1H, J=8.7 Hz), 7.15 (t, 1H, J=7.5 Hz), 4.80 (m, 1H), 4.26 (d, 2H, J=6.0 Hz), 1.33 (s, 3H), 1.31 (s, 3H). MS (ES+) m/e 382 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With palladium diacetate; cesium fluoride; In 1,2-dimethoxyethane; water; for 1h;Reflux; | General procedure: Method A: Boronic acid 3 (2.4 mmol) and then CsF (2.5 mmol, 0.38 g) dissolved in H2O (5 mL) were added to a stirring mixture of 7-iodoisatin (2a, 2 mmol, 0.54 g) or 7-bromo-8-methylisatin (2b, 2 mmol, 0.48 g) and Pd(OAc)2 (0.2 mmol; 24 mg) in DME (6 mL), first. The mixture was stirred at reflux until the disappearance of 2a or 2b, monitoring the reactions by TLC (CH2Cl2-EtOAc, 9.8:0.2), GC and GC-MS. Then, the reaction mixture was poured into CH2Cl2-H2O (100 ml, 1:1). The aqueous layer was separated and extracted with CH2Cl2 (2×50 mL). The combined organic extracts were washed with H2O (2×50 mL), dried over Na2SO4 and evaporated under reduced pressure. The crude residue, purified in a chromatography column (CH2Cl2-EtOAc, 98:2), afforded pure 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; ethanol; water; for 2h;Inert atmosphere; Reflux; | To a solution of 4 (1 equiv.) in dry DME (0.05 M solution), Pd(PPh3J4 (0.07 equiv.) was added and the mixture stirred for 15 minutes under N2 atmosphere. A solution of 2- (isopropyloxyphenyl)-boronic acid (1.1 equiv.) in a minimal amount of EtOH was added followed by a saturated aqueous NaHCO3 solution (1/3 of the DME volume). The mixture was refluxed under a nitrogen atmosphere for 2 h, cooled to room temperature, and extracted with DCM. The collected organic layers were dried over magnesium sulfate, filtered, the solvent removed under reduced pressure and the crude material purified by flash chromatography.Ethyl 4-/so-butyl-6-(2-phenoxyphenyl)pyridazine-3-carboxylate 16a: Rf = 0.42 (Hexane/AcOEt = 80:20). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (R)-[2'-(2,6-dimethoxyphenyl)-1,1'-binaphthalene-2-yl]diphenylphosphane; palladium diacetate; cesium fluoride; In tetrahydrofuran; for 72h;Reflux; Inert atmosphere; | General procedure: General procedure: A round bottom flask equipped with a magnetic stirrer bar and a condenser was charged with solid materials: boronic acid 7 (0.18mmol), base (0.3mmol), Pd(OAc)2 (0.005mmol, 1.12mg), and ligand (R)-1 (0.02mmol), and then purged three times under argon without any solvent. A solution of bromide 8 or 10 (0.1mmol) in solvent (1.25ml) was injected and this mixture was stirred for 72h at reflux unless said otherwise. After this time, the flask was allowed to warm to room temperature, after which dichloromethane (5ml) and water (5ml) were added to this mixture. The layers were separated and the aqueous layer was extracted with dichloromethane (3×5ml). The combined organic layers were dried over anhydrous Na2SO4, filtered, and the solvent evaporated under reduced pressure. The crude mixture was purified by column chromatography over silica gel, to give the corresponding products. Enantiomeric excesses were determined by HPLC using Chiralcel OD-H, AD-H, or OJ-H (Daicel Chemical Industries) column. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (R)-[2'-(2,6-dimethoxyphenyl)-1,1'-binaphthalene-2-yl]diphenylphosphane; palladium diacetate; cesium fluoride; In tetrahydrofuran; for 72h;Reflux; Inert atmosphere; | General procedure: General procedure: A round bottom flask equipped with a magnetic stirrer bar and a condenser was charged with solid materials: boronic acid 7 (0.18mmol), base (0.3mmol), Pd(OAc)2 (0.005mmol, 1.12mg), and ligand (R)-1 (0.02mmol), and then purged three times under argon without any solvent. A solution of bromide 8 or 10 (0.1mmol) in solvent (1.25ml) was injected and this mixture was stirred for 72h at reflux unless said otherwise. After this time, the flask was allowed to warm to room temperature, after which dichloromethane (5ml) and water (5ml) were added to this mixture. The layers were separated and the aqueous layer was extracted with dichloromethane (3×5ml). The combined organic layers were dried over anhydrous Na2SO4, filtered, and the solvent evaporated under reduced pressure. The crude mixture was purified by column chromatography over silica gel, to give the corresponding products. Enantiomeric excesses were determined by HPLC using Chiralcel OD-H, AD-H, or OJ-H (Daicel Chemical Industries) column. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.29 g | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; cesium fluoride; In 1,4-dioxane; at 90℃; for 3h; | Preparation example 116A mixture of Present compound (T057) 0.30 g, 2- isopropyloxyphenylboronic acid 0.28 g, cesium fluoride 0.42g, [1,1? -bis (diphenylphosphino) ferrocenelpalladium(II) dichioride dichioromethane adduct 0.06 g and dioxane 6 mL was stirred at 90C for three hours. After cooling the reaction mixtures, the mixtures were filtered and the filtrates were concentrated under reduced pressure. Theresulting residues were subjected to a silica gel column chromatography to give 2-{ [1- (4, 5-dihydro-4-methyl-5-oxo- 1H-tetrazole-l-yl) -3-methylphenyl-2--yl]methyloxy}-4- (2- isopropyloxyphenyl)thiazole (hereinafter, referred to as ??Present compound (T116) ??) 0.29 g.?H NMR (CDC13) 6: 1.41(6H, d, J=6Hz), 2.57(3H, s), 3.59(3H, s), 4.66-4.75(1H, rn), 5.58(2H, s), 6.95(1H, d, J=8.2Hz), 7.00(1H, t, J=7.7Hz), 7.20-7.31(2H, rn), 7.45-7.39(3H, rn),8.12(1H, dd, J=7.7, 1.7Hz) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | [0095] Pd(PPh3)4 (187 mg, 0.162 mmol, 10%) was added to a solution of 3-((tert-butyldimethylsilyloxy)methyl)-2-chloroquinoline (0.5 g, 1 .62 mmol) in dioxane (10 mL) and stirred for 10 mm at 25C. To the resulting mixture, a solution of <strong>[138008-97-6]2-isopropoxyphenylboronic acid</strong> (0.438 g, 2.43 mmol, 1.5 eq) in EtOH (4 mL) was added and the resulting mixture was stirred at 25C for 10 minutes before the addition of a 2 M aqueous solution of sodium carbonate (8.1 mL, 16.2 mmol, 10 eq). The resulting mixture was stirred at 25C for an additional 5 minutes, then heated to 80C for 24 hours. Upon completion, the mixture was diluted with water and extracted 3 times with EtOAc. The combined organic layers were dried (Na2504), concentrated, and the crude material was purified by combi flash 0->20% EtOAc in hexanes to provide 3- ((tert-butyldimethylsilyloxy)methyl)-2-(2-isopropoxyphenyl)quinoline (0.57 g, 86% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With potassium phosphate; ((2-dicyclohexylphosphino-2',4?,6?-triisopropyl-1,1?-biphenyl)[2-(2?-amino-1,1?-biphenyl)]palladium(II) methanesulfonate); In tetrahydrofuran; water; at 40℃; for 16h;Inert atmosphere; | Under argon, tert-butyl 4-(10-bromo-2-oxo-l,2-dihydropyrimido[l,2-b]indazol-4-yl)piperidine-l- carboxylate (0.20 g, 0.48 mmol), <strong>[138008-97-6]2-isopropoxyphenylboronic acid</strong> (89 mg, 0.49 mmol) and (2- dicyclohexylphosphino-2',4',6'-triisopropyl- 1 , 1 '-biphenyl) [2-(2'-amino- 1 , 1 '-biphenyl)]palladium(II) methanesulfonate (11 mg, 13 muiotaetaomicron) were dissolved in degassed tetrahydrofuran (4 mL). Potassium phosphate solution (1 M in water, degassed) (2.65 mL, 2.65 mmol) was added and the mixture was stirred at 40 C for 16 h. The phases were separated and the organic phase was subjected to preparative HPLC (Method 1A) to afford the title compound (134 mg, 59% of theory). LC-MS (Method IB): Rt = 1.33 min, MS (ESIPos): m/z = 503 [M+H]+ |
134 mg | With potassium phosphate; methanesulfonic acid(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl-1,1?-biphenyl)[2-(2?-amino-1,1?-biphenyl)]palladium(II); In tetrahydrofuran; water; at 40℃; for 16h;Inert atmosphere; | Example 161A Tert-butyl 4-[10-(2-isopropoxyphenyl)-2-oxo-1,2-dihydropyrimido[1,2-b]indazol-4-yl]piperidine-1-carboxylate Under argon, tert-butyl 4-(10-bromo-2-oxo-1,2-dihydropyrimido[1,2-b]indazol-4-yl)piperidine-1-carboxylate (0.20 g, 0.48 mmol), <strong>[138008-97-6]2-isopropoxyphenylboronic acid</strong> (89 mg, 0.49 mmol) and (2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl) [2-(2'-amino-1,1'-biphenyl)]palladium(II) methanesulfonate (11 mg, 13 mumol) were dissolved in degassed tetrahydrofuran (4 mL). Potassium phosphate solution (1 M in water, degassed) (2.65 mL, 2.65 mmol) was added and the mixture was stirred at 40 C. for 16 h. The phases were separated and the organic phase was subjected to preparative HPLC (Method 1A) to afford the title compound (134 mg, 59% of theory). LC-MS (Method 1B): Rt=1.33 min, MS (ESIPos): m/z=503 [M+H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; water; sodium carbonate; In N,N-dimethyl-formamide; at 75℃; for 21h; | Methyl 3-{5-[4-({4-bromo-N-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)-carbonyl]-L-phenylalanyl}amino)phenyl]-4H-1,2,4-triazol-3-yl}-2,2,3,3-tetrafluoropropanoate (100 mg, 0.13 mmol) and (2-isopropoxyphenyl)boric acid (27 mg, 0.15 mmol) were dissolved in 1 ml dimethylformamide, aqueous sodium carbonate solution (2M, 0.13 ml, 0.26 mmol) was added and the mixture was degassed. After addition of 9 mg (0.01 mmol) of 1,1'-bis(diphenylphosphino)ferrocenepalladium(II) chloride, the reaction mixture was stirred at 75 C. for 18 h. More (2-carbamoylphenyl)boric acid (80 mg, 0.1 mmol), aqueous sodium carbonate solution (2M, 0.13 ml, 0.26 mmol) and 9 mg (0.01 mmol) of 1,1'-bis(diphenylphosphino)ferrocenepalladium(II) chloride were added, and the reaction mixture was stirred at 75 C. for 3 h. The reaction solution was filtered through a Millipore syringe filter and purified via preparative HPLC (mobile phase: acetonitrile/water with 0.1% trifluoroacetic acid (gradient)). This gave 59 mg (51% of theory) of the title compound. LC-MS (Method 1): Rt=1.26 min; MS (ESIpos): m/z=825.2 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15% | With potassium carbonate; In 1,4-dioxane; water; at 100℃; for 1h;Inert atmosphere; | General procedure: The 6-iodopyrrolopyrimidine (6a - 6c, 7a - 7b or 7d) (50-350mg) was mixed with the selected arylboronic acid (1.2 eq), fine powdered K2CO3 (3 eq), XPhos (5mol %)/2nd generation XPhos precatalyst (5mol %) system or PdCl2(dppf) (5mol %) and mixture with degassed 1,4-dioxane/H2O (1/1 by vol. %, 2-8mL). The reaction was then stirred at 100C for 0.5-10h under N2 atmosphere. The solvent was removed and the product was diluted with H2O (25-100mL) and extracted with EtOAc (50-120mL), several times if required. The combined organic phases were washed with saturated aq. NaCl solution (30mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. Purification was performed as described for each individual compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,4-dioxane; water; at 80℃; for 1h;Inert atmosphere; Microwave irradiation; | Compound 2-a (50 mg, 0.15 mmol), <strong>[138008-97-6]2-isopropoxybenzeneboronic acid</strong> (42 mg, 0.23 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (13 mg, 0.12 mmol) and sodium carbonate (66 mg, 0.62 mmol) were dissolved in 1,4-dioxane (2 mL) and water (0.2 mL). The reaction solution was purged with nitrogen gas for three times to remove oxygen contained in the system, and heated at 80 C. under microwave for 1 hour. The reaction was cooled to room temperature, diluted with ice water (10 mL) and extracted with dichloromethane (20 mL*3). The combined organic phase was washed with water (10 mL*3) and brine (10 mL) successively, dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure. The residue was purified by preparative HPLC (mobile phase: 10 mM aqueous ammonium bicarbonate solution: acetonitrile=50% to 80%) to give 29 as a white solid (14 mg, yield 24%). LC-MS (ESI): m/z=380[M+H]+. 1H-NMR (400 MHz, CDCl3) delta: 8.73 (s, 1H), 7.83 (s, 1H), 7.45-7.37 (m, 3H), 7.12-7.04 (m, 2H), 6.89 (s, 1H), 4.39-4.35 (m, 1H), 3.77 (s, 3H), 2.51 (s, 3H), 1.25 (d, J=6 Hz, 3H), 1.06 (d, J=6 Hz, 3H) ppm |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With tris-(dibenzylideneacetone)dipalladium(0); sodium carbonate; tri tert-butylphosphoniumtetrafluoroborate; In 1,4-dioxane; water; at 90℃; for 3h; | A mixture of 4-bromo-5-chlorobenzene-1,2-diamine (1.1 g, 5.0 mmol), (2- isopropoxyphenyl)boronic acid (1.1 g, 6.1 mmol), tris-(dibenzylideneacetone) dipalladium(0) (454 mg), tri(tert-butyl)phosphonium tetrafluoroboronate (288 mg) and sodium carbonate (1.8 g 14.5 mmol) in 1,4-dioxane (100 ml) and water (10 mL) was degassed, heated to 90 C under for 3h. The volatile solvents were removed under reduced pressure. The residue was directly loaded onto a ISCO solid cartridge and flashed with hexane/ethyl acetate to afford a white solid product 1.1 g (80% yield), MS (+) ES: 277 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With tris-(dibenzylideneacetone)dipalladium(0); sodium carbonate; tri tert-butylphosphoniumtetrafluoroborate; In 1,4-dioxane; at 100℃; for 1h;Sealed tube; Microwave irradiation; | A mixture of 5-bromo-6-chloro-2-(4-((cyclopropylmethyl)sulfonyl)benzyl)-1H- benzo[d]imidazole (step 5) (439 mg, 1 mmol), <strong>[138008-97-6](2-isopropoxyphenyl)boronic acid</strong> (495 mg, 3 mmol), tris-(dibenzylideneacetone)dipalladium(0) (60 mg), tri(tert-butyl)phosphonium tetrafluoroboronate (60 mg) and sodium carbonate (2 ml ml, 2M solution) in 1,4-dioxane (8 ml) was degassed, sealed and heated to 100 C under Microwave irradiation for 60 min. The volatile solvents were removed under reduced pressure. The residue was directly taken into DCM and loaded onto an ISCO solid cartridge and flashed with hexane/ethyl acetate to afford a white solid product 355 mg (72% yield), MS (+) ES: 495 (M+H) +. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With palladium diacetate; dicyclohexylphenylphosphine; potassium hydroxide; In 1,4-dioxane; at 100℃; for 24h;Inert atmosphere; Schlenk technique; | Under an argon atmosphere, in a Schlenk bottle,Charge 1 mmol of bis[3,5-bis(trifluoromethyl)phenyl](2-bromoacenaphthylen-1-yl)phosphane and 1.2 mmol of <strong>[138008-97-6]2-isopropoxyphenylboronic acid</strong> (Shanghai Biode Medical Technology Co., Ltd.), 0.1mmol palladium acetate,0.2 mmol of PhPCy2 and 3 mmol of potassium hydroxide were added to 5 mL of 1,4-dioxane to dissolve the reaction. Reaction at 100 C for 24 hours,After cooling, the reaction solution was extracted with ethyl acetate, washed with a saturated sodium chloride solution, and the organic phase was dried over anhydrous sodium sulfate. The organic phase solvent was removed, and petroleum ether: ethyl acetate = 100: 1 was used as a developing agent (Rf = 0.85). Column chromatographybis[3,5-bis(trifluoromethyl)phenyl]({2-[2-(propan-2-yloxy)phenyl]acenaphthylen-1-yl})phosphane was obtained in a yield of 66%. |
Tags: 138008-97-6 synthesis path| 138008-97-6 SDS| 138008-97-6 COA| 138008-97-6 purity| 138008-97-6 application| 138008-97-6 NMR| 138008-97-6 COA| 138008-97-6 structure
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P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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