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CAS No. : | 248924-59-6 | MDL No. : | MFCD03453669 |
Formula : | C10H15BO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KTBLRYUFNBABGO-UHFFFAOYSA-N |
M.W : | 194.04 | Pubchem ID : | 2773996 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.6 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 55.18 |
TPSA : | 31.6 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.08 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 1.97 |
Log Po/w (WLOGP) : | 1.58 |
Log Po/w (MLOGP) : | 0.34 |
Log Po/w (SILICOS-IT) : | 1.25 |
Consensus Log Po/w : | 1.03 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.48 |
Solubility : | 0.639 mg/ml ; 0.00329 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.26 |
Solubility : | 1.07 mg/ml ; 0.00551 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.21 |
Solubility : | 0.119 mg/ml ; 0.000612 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.19 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-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 |
---|---|---|
11% | With meso-tetra(p-tolyl)porphinato-palladium(II); potassium acetate In 1,4-dioxane at 110℃; for 15 h; | General procedure: Aryl/heteroaryl bromide 1 (1 mmol), B2pin2(2), B2npg2(4) orBpin (6, 1.2 mmol), and dioxane (5 mL) are taken into a 25 mLround-bottomed flask. KOAc (2 mmol) was added and stirredthe resultant mixture at room temperature for 5 min, PdII-TpTP(0.15 molpercent) was added, and the contents were refluxed on preheatedoil bath at 110 °C under constant stirring in open-air.The reaction progress was ensured by TLC. After completion ofthe reaction, the mixture was cooled, dilute with water (20 mL)and extracted with tertbutylmethyl ether (3 × 10 mL). The combinedn-hexane layers were concentrated, and the crudeproduct obtained was purified by column chromatography (CC)on silica gel using a mixture of ethyl acetate and hexane (1:30)as eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; water; at 120℃; for 0.333333h;Microwave; | 1,1-Dimethylethyl (2R,6S)-4-[6-[(4-bromo-2-chlorophenyl)sulfonyl]amino}-5-(methyloxy)-2-pyridinyl]-2,6-dimethyl-1-piperazinecarboxylate (D13) (0.15 g, 0.254 mmol), 2-(3-furanyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.0739 g, 0.381 mmol), Palladium dichloride di-triphenylphosphine (9.0 mg, 0.0127 mmol), sodium carbonate (0.053 g, 0.508 mmol) were heated in DME (2 mL) and water (1 mL) at 120 C. in the microwave for 20 minutes. The reaction was then diluted with ethyl acetate (50 mL) and washed with saturated sodium hydrogen carbonate (2×30 mL) and brine (30 mL). The organic layer was dried (MgSO4) and evaporated to give a yellow oil which was purified by chromatography [silica gel, eluting with 0 to 60% Ethyl acetate/pentane]. Product fractions evaporated to give a pale yellow foam (D15) (0.170 g) MS (ES+) m/e 577/579 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 95℃; for 3h; | Example 33: Synthesis of 4-[(3-chloro-5-trifluoromethyl-benzyl)-(5-furan-3-yl- pyrimidin-2-yl)-amino]-2,6-diethyl-piperidine-1-carboxylic acid isopropyl ester; A mixture of 4-[(5-bromo-pyrimidin-2-yl)-(3-chloro-5-trifluoromethyl-benzyl)-amino]- 2,6-diethyl-piperidine-1-carboxylic acid isopropyl ester (0.1 mmol, 59 mg), 2-furan-3-yl- 4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolane (0.15 mmol, 29 mg), tetrakis(triphenylphosphine)palladium(0) (0.01 mmol, 11.5 mg) and sodium hydrogen carbonate (0.2 mmol, 17 mg) in 1 ,2-dimethoxy-ethane (1 ml_) and water (0.4 mL) is allowed to warm to 95 0C and stirred for 3 hours. The mixture is cooled to room temperature and then added water. The mixture is extracted with CH2CI2. The combined organic layer is washed with brine, dried over Na2SO4, filtrated, and concentrated under reduced pressure. The obtained residue is purified by silica gel column chromatography (eluent: hexane / EtOAc) to give 4-[(3-Chloro-5-trifluoromethyl-benzyl)-(5-furan-3-yl-pyrimidin-2-yl)-amino]- 2,6-diethyl-piperidine-1-carboxylic acid isopropyl ester (34 mg, 59%); ESI-MS m/z: 579 [M+1] Retention time 2.60 min (condition A). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18% | With potassium fluoride; tetra-(n-butyl)ammonium iodide;trans-bis(triphenylphosphine)palladium dichloride; In water; toluene; for 12h;Heating / reflux; | Example 10; 4-(Furan-3 '-yl)furan-2(5H)-one 10; A mixture containing 4-bromo-5(H)furanone (0.261 g, 1.602 mmol), pinacolate(3- furanboronic) ester (0.392 g, 2.020 mmol), trans- dichlorobis(triphenylphosphine)palladium (II) (0.058 g, 8.263xlO'2 mmol), tetrabutylammonium iodide (0.062 g, 1.678XlO"1 mmol) and potassium fluoride (0.393 g, 6.764 mmol) in toluene (10 mL) and water (10 mL) were gently refluxed for 12 h under nitrogen before the reaction mixture was allowed to cool to room temperature. Brine (50 mL) was added and the product extracted with dichloromethane (3x20 mL). The organic fractions were combined, washed with brine (3x20 mL), dried over anhydrous magnesium sulfate and evaporated to dryness under reduced pressure to give a dark brown solid. The resulting solid was chromatographed (silica gel: eluent 50:50 dichloromethane/light petroleum followed by 100% dichloromethane) to give 4-(3 '-furan)furan-2(5H)-one 10 (0.043 g, 18%) as brown needles, m.p. 101-1020C (ref. PDS-2-11). UV- Vis lambdamax (MeOH) 244(1724) nm; 1H NMR (CDCl3, 300 MHz) delta 7.73 (s, IH, H21), 7.53 (t, IH, J = 1.5 Hz, H51), 6.60 (t, IH, J = 1.1 Hz, H3), 6.11 (t, IH, J= 1.5 Hz, H41), 5.06 (d, 2H, J= 1.9 Hz, H5); 13C NMR (CDCl3, 75 MHz) delta 173.7 (C2), 156.2 (C4), 145.0 (C41), 141.9 (Cl'), 117.5 (C21), 112.4 (C3), 108.2 (C31), 70.8 (C5); IR (KBr) 3141, 3114, 3051, 1790, 1736, 1673, 1519, 1470, 1447, 1405, 1355, 1322, 1275, 1236, 1158, 1019, 894, 871, 852, 828, 752, 702, 644, 596, 547, 527, 501 ran 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3-(4,4,5,5-Tetramethyl-[1,3,2]-dioxaborolan-2-yl)-furan is prepared as follows: t-BuLi (40 mL of 1.7 M solution, 68 mmol) is added dropwise to a solution of 3-bromofuran (5.0 g, 34 mmol) in 100 mL of THF at -78 C., and the reaction mixture is stirred at -78 C. for 5 min. B(O-i-Pr)3 (23 mL, 100 mmol) is added, the cooling bath is removed, and the reaction mixture is stirred at room temperature for 18 h, and then cooled to 0 C. The reaction mixture is then quenched with 50 mL of 2N HCl, and extracted three times with EtOAc. The organic phases are combined, and washed with brine, dried over MgSO4, filtered, and concentrated. The residue is dissolved in 200 mL of CH2Cl2. Pinnacol (20 g), and Na2SO4 (100 g) are added, and the mixture is stirred at room temperature overnight, and then filtered. The solution is concentrated and purified by chromatography on silica gel (gradient elution with 10-40% EtOAc/hexane) to provide the desired product as a yellow solid; mp 52-55 C.; 1H NMR (250 MHz, CDCl3) delta7.78 (s, 1H), 7.46 (dd, 1H), 6.59 (d, 1H), 1.32 (s, 12H); IR (CH2Cl2, cm-1) 1300, 1269, 1138. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; at 80℃; for 12h; | To a mixture of <strong>[68819-84-1]tert-butyl N-(4-bromobenzyl)carbamate</strong> (0.14 g), 2-(furan-3-yl)-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane (0.12 g), potassium carbonate (0.1 g), water (0.2 mL) and N,N-dimethylformamide (1 mL) was added tetrakis(triphenylphosphine)palladium(0) (0.03 g), and the resulting mixture was stirred at 80 C. for 12 hours. The reaction mixture was cooled to room temperature and then the insoluble material was filtered out. The filtrate was partitioned between ethyl acetate (110 mL) and water (50 mL). The organic layer was washed successively with water (50 mL) and brine (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on aminopropylated silica gel (eluent: hexane/ethyl acetate=1/1) to give tert-butyl N-[4-(furan-3-yl)benzyl]-carbamate. The compound obtained was dissolved in dichloromethane (5 mL), trifluoroacetic acid (0.57 mL) was added dropwise, and the resulting mixture was stirred at room temperature for 2 hours. Saturated aqueous sodium hydrogen carbonate (15 mL) was added dropwise and the whole was extracted with dichloromethane (30 mL). The organic layer was washed with saturated aqueous sodium hydrogen carbonate/brine (1/1, 10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound (0.06 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; sodium hydroxide; sodium carbonate; In ethanol; N,N-dimethyl acetamide; ethyl acetate; | Example 14 61 mg of <strong>[248924-59-6]3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan</strong>, 55 mg of sodium carbonate and 30 mg of polymer supported bis(acetato)triphenylphosphine palladium(II) were added to 2.5 mL of N,N-dimethylacetamide solution containing 70 mg of methyl 2- (benzamido) -4-bromobenzoate, and stirred at 90C for 12 hours. After the reaction mixture was cooled to room temperature, 41 mg of <strong>[248924-59-6]3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan</strong> and 22 mg of sodium carbonate were added and stirred at 90C for 12 hours. After the reaction mixture was cooled to room temperature, insoluble were removed by filtration and ethyl acetate and 1.0 mol/L hydrochloric acid were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with 1.0 mol/L hydrochloric acid and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. 1.0 mL of 2.0 mol/L aqueous sodium hydroxide and 2.0 mL of ethanol were added to the obtained residue and stirred at room temperature for 1 hour. 0.6 mol/L hydrochloric acid was added to the reaction mixture, and solid substances were separated by filtration and purified with reversed-phase silica gel column chromatography [eluent; 50-100% acetonitrile /0.1% trifluoroacetic acid aqueous solution] to obtain 6.2 mg of 2-(benzamido)-4-(furan-3-yl)benzoic acid as white solid. 1H-NMR (DMSO-d6) delta: 6.97 (1H, d, J = 1.7 Hz), 7.47 (1H, dd, J = 8.3, 1.7 Hz), 7.59-7.69 (3H, m), 7.83 (1H, t, J = 1.6 Hz), 7.98-8.00 (2H, m), 8.06 (1H, d, J = 8.3 Hz), 8.32 (1H, s), 8.94 (1H, d, J = 1.7 Hz), 12.29 (1H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 110℃;Sealed tube; | Example 9 Synthesis of {4-[4-(4-Furan-3-yl-benzotriazol-1-yl)-pyrimidin-2-ylamino]-cyclohexyl}-(4-hydroxy-piperidin-1-yl)-methanone (Compound 9) A mixture of (4-hydroxy-piperidin-1-yl)-{4-[4-(4-iodobenzotriazol-1-yl)-pyrimidin-2-yl-amino]-cyclohexyl}-methanone (274 mg) and 3-(4,4,5,5-tetramethyl-1,3,2-dioxoborolan-2-yl)-furan (102 mg) was placed in a screw cap pressure flask, and Na2CO3 (2 M aq, 0.7 mL, degassed), toluene (5 mL, degassed) and EtOH (5 mL) added. To this was added Pd(PPh3)4 (20 mg), the flask sealed, and the mixture stirred overnight at 110 C. The reaction mixture was then cooled to RT, diluted in water, extracted in DCM, washed with water and brine, dried over Na2SO4, and the solvent stripped to yield a crude solid. The crude product was chromatographed on silica, and eluted with 0-60% Magic Base/DCM, titurated in Et2O overnight, filtered, and evaporated to yield {4-[4-(4-furan-3-yl-benzotriazol-1-yl)-pyrimidin-2-ylamino]-cyclohexyl}-(4-hydroxy-piperidin-1-yl)-methanone (Compound 9, 103 mg). mp=243.0-244.0 C.; M+H=488. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A suspension of (1S,4aR,6aS,7/e,8R,10aR,10bi?,12aR,14/,15R)-15-[[(2R)-2- amino-2,3-dimethylbutyl]oxy]- 14-(5-bromo-7H- 1 ,2,4-triazol- 1 -yl)-8-[( 1R)- 1 ,2-dimethylpropyl]- 1 ,6,6a,7,8,9, 10, 10a, 10b, 11,12,12a-dodecahydro- 1 ,6a,8, 10a-tetramethyl-4H- 1 ,4a-propano-2H- phenanthro[1,2-c]pyran-7-carboxylic acid (Example 6B, 7.8 mg, 0.011 mmol), cesium carbonate (139 mg, 0.427 mmol), <strong>[248924-59-6]3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan</strong> (24 mg, 0.124 mmol), palladium (II) acetate (3.5 mg, 0.016 mmol) and 2-dicyclohexylphosphino-2',4',6'- triisopropylbiphenyl (2.2 mg, 0.005 mmol) in ethanol (0.2 mL) and water (0.1 mL) was blanketed with nitrogen and placed in a 80C oil bath for 2.5 hours. The mixture was cooled to room temperature, filtered and purified by reverse phase EtaPLC using a 19 x 150 mm Sunfire Preparative C18 OBD column eluting with acetonitrile/water + 0.1% TFA. Product fractions were evaporated and freeze-dried from a mixture of ethanol and benzene to give the title compound as a TFA salt (2.0 mg)1H NMR (CD3OD, 600MHZ, ppm) delta 0.76 (s, 3H, Me), 0.77 (d, 3H, Me), 0.77 (s, 3H, Me), 0.78 (d, 3H, Me), 0.80 (d, 3H, Me), 0.86 (d, 3H, Me), 0.87 (s, 3H, Me), 0.89 (d, 3H, Me), 1.16 (s, 3H, Me), 1.21 (s, 3H, Me), 1.23-1.34 (m), 1.40-1.44 (m), 1.48-1.72 (m), 1.82-2.02 (m), 2.12-2.21 (m), 2.41 (dd, 1H, H13), 2.84 (s, 1H, H7), 2.86 (d, 1H), 3.46 (d, 1H), 3.50 (d, 1H), 3.57 (dd, 1H), 3.68 (d, 1H), 3.91 (d, 1H), 3.93 (d, 1H), 5.53 (dd, 1H, H5), 5.90 (m, 1H, H14), 6.91 (d, furan), 7.74 (dd, furan), 8.07 (br s) and 8.13 (br s, 1H).Mass spectrum: (ESI) mJz = 705.42 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; for 8h;Reflux;Product distribution / selectivity; | (ii) 5-Chloro-2-([(2-([3-(furan-3-yl)phenyl]amino)-2-oxoethoxy)acetyl]amino)benzoic acid·methyl ester; Using the same method as in Example 5-(i), <strong>[248924-59-6]3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan</strong> was reacted with the 2-[((2-[(3-bromophenyl)amino]-2-oxoethoxy)acetyl)amino]-5-chlorobenzoic acid·methyl ester obtained in Example 19-(i) to give 5-chloro-2-([(2-([3-(furan-3-yl)phenyl]amino)-2-oxoethoxy)acetyl]amino)benzoic acid·methyl ester (yield: 75%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; for 22h;Reflux; | (i) N-Ethyl-5-(furan-3-yl)-2-methylaniline 0.69 g (3.20 mmol) of 5-bromo-N-ethyl-2-methylaniline and 0.93 g (4.80 mmol) of 3-furan boronic acid pinacol ester were dissolved in 7 mL of THF. 1.56 g (4.80 mmol) of cesium carbonate and 370 mg (0.32 mmol) of tetrakis(triphenyl phosphine)palladium(0) were added thereto and heated under reflux for 22 hours. After completion of the reaction, filtration was conducted, and the filtrate was condensed. The resulting crude product was separated and purified using silica gel column chromatography to give N-ethyl-5-(furan-3-yl)-2-methylaniline (yield: 98%). 1H-NMR (CDCl3) delta: 1.33 (3H, t, J = 7.0 Hz), 2.14 (3H, s), 3.24 (2H, q, J = 7.0 Hz), 3.40 (1H, br), 6.67-6.71 (2H, m), 6.78 (1H, dd, J= 7.6, 1.8 Hz), 7.04 (1H, d, J = 7.6 Hz), 7.44-7.45 (1H, m), 7.67-7.69 (1H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 90℃; for 16h;Inert atmosphere; sealed vessel; | A mixture of 25 mg of 9ca, 13 mg OfK2CO3 , 10 mg of 4,4,5,5-tetramethyl-2-(3-furyl)- 1,3,2-dioxaborolane and 5 mg of tetrakis (triphenylphosphine) palladium in 3 ml of degassed 90% aq. dimethoxyethane was heated in a sealed vessel under N2 atmosphere for 16 hr at 9O0C as described for 7ca to give 12 mg of 9cd. MS-ESI: [M+H]+ 514.4. NMR(CDCl3) delta 1.05 and 1.10 (2x d, 6, oC3H7), 1.52 and 1.54 (2x s, 9, tertC4H9), 2.80-3.00 (bm, 4, CH2CH2), 3.04 (s, 3, NCH3), 3.81 (s, 3, OCH3), 3.77 (m, 1, CH), 6.12 and 6.53 (2x s,, 2, Ar-H) 6.16 and 6.90 and 7.25 (3x m, 3, 3-furyl-H), 7.40-7.65 (m, 4, phenyl-H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Alternative Route to Intermediate 3: 3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-furan (5.0 g, 25.77 mmol) is dissolved in dry acetonitrile (30 mL). Chlorosulfonylisocyanate (5.47 g, 38.65 mmol, 1.5 equiv.) in solution in dry acetonitrile (20 mL) is added in one portion at room temperature to the furan producing a pink solution that subsides overnight to turn yellow. The resulting solution is cooled with an ice bath and water (5 mL) is added, causing an exotherm. The resulting mixture is partitioned between DCM (100 mL) and water (30 mL). The aqueous layer is extracted 3 more times with DCM (50 mL), then the organic layers are gathered, washed with brine (10 mL), dried over anhydrous Na2SO4 and finally the solvent is removed under vacuum. The oily residue is dissolved in DCM (3 mL), sonicated to give a suspension of a crystalline solid. The solid is separated by filtration, and the cake is washed with a very small amount of DCM, then diethyl ether and dried under suction to afford 3 g of the title compound as a white powder. NMR 1H (400 MHz, DMSO-d6) delta ppm: 8.16 (1H, m); 7.15 (1H, m); 7.11 (1H, s); 4.33 (2H, q); 1.38 (3H, t); 1.34 (12H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 110℃; for 12h;Inert atmosphere; Sealed vial; | Example 42-[2-(4-Furan-3-yl-1 -methyl-1 H-imidazol-2-yl)-ethyl]-8-methoxy-5-methyl- [1,2,4]triazolo[1 ,5-a]pyridine A glass vial was charged with 2-[2-(4-Bromo-1 -methyl-1 H-imidazol-2-yl)-et hyl]-8-methoxy-5-methyl-[1 ,2,4]triazolo[1 ,5-a]pyridine (70 mg, 0.20 mmol), furan-3- boronic acid (33.6 mg, 0.30 mmol), 1 ,2-dimethoxyethane (0.8 mL), 1 M solution of sodium carbonate in water (0.3 mL) and the slurry was deoxygenated by bubbling argon through then tetrakis(triphenylphosphine)palladium(0) (5.2 mg, 0.0045 mmol) was added and the vessel sealed and heated at 1 10C for 12 hours. EtOAc (3 mL) was added followed by brine solution (2 mL). The organic layer was separated and the volatiles removed in vacuo. The residue was purified by column chromatography on silica gel (gradient 100% EtOAc to EtOAc :MeOH, 7:3) to yield the title compound (10 mg, 10%). LCMS (MH+): m/z = 338.1 , tR (minutes, method B) =0.41 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With potassium carbonate;palladium diacetate; In 1-methyl-pyrrolidin-2-one; water; at 25 - 110℃; for 0.283333h;Microwave irradiation; | Example 1.11 : 2-(Furan-3-yl)-1H-indole.A mixture of 2-iodo-1 /-/-indole (0.25 g, 0.001 mol) [2-iodo-1 H- indole is prepared according to literature: Bergman, J.; Venemalm, L. Efficient synthesis of 2-chloro-, 2-bromo-, and <strong>[26340-49-8]2-iodoindole</strong>. J. Org. Chem. 1992, 57, 2495-2497], furan-3-boronic acid pinacol ester (0.26 g, 0.00134 mol), palladium (II) acetate (10%, 0.03 g, 0.000134 mol) and potassium carbonate (0.18 g, 0.00134 mol) in 1-methyl-2-pyrrolidone (2.3 ml_) containing 0.18 mL of water is treated by microwave irradiation at 200 W in closed vessel at 110C per 15 min (temperature ramp from 25C to 1 10C in 2 minutes). After cooling the mixture is diluted with water under stirring and extracted with ethyl acetate. The organic layer is washed with water and dried. After solvent removal the solid residue is purified by column chromatography (silica gel, ethyl acetate: n- hexane 1 :5 as eluent) to give 2-(furan-3-yl)-1 /-/-indole (0.18 g, 95%), melting point 145-148C (after ethanol crystallization). 1H NMR (CDCI3): 5 6.61-6.62 (m, 1 H), 6.70-6.71 (m, 1 H), 7.09-7.19 (m, 2H), 7.36 (dd, J = 0.87 and 8.0 Hz, 1 H), 7.50-7.52 (m, 1 H), 7.58-7.60 (m, 1 H), 7.75 (m, 1 H), 8.10 ppm (br s, 1 H, it disappears after treatment with D2O). IR: v 3417 cm"1. Anal. (C12H9NO (183.21)) C, H, N. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; water; for 1.66667h;Inert atmosphere; Reflux; | Example 69a [Show Image] Water (0.5 mL), <strong>[248924-59-6]3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan</strong> (0.070 g), sodium carbonate (0.076 g), and bis(triphenylphosphine)palladium(II) dichloride (4.2 mg) were added to an ethylene glycol dimethyl ether (1.7 mL) solution of tert-butyl 2-(2-(benzyloxy)-5-bromobenzamido)-4-phenylbenzoate (0.17 g), followed by heating to reflux under a nitrogen atmosphere for 1 hour and 40 minutes. The reaction mixture was cooled to room temperature, and water and ethyl acetate were added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 95-80% hexane/ethyl acetate] to obtain 0.14 g of tert-butyl 2-(2-(benzyloxy)-5-(furan-3-yl)benzamido)-4-phenylbenzoate as a white solid. 1H-NMR (CDCl3) delta: 1.53 (9H, s), 5.50 (2H, s), 6.67-6.73 (1H, m), 6.97 (1H, d, J=8.8 Hz), 7.24-7.53 (11H, m), 7.67-7.79 (3H, m), 8.07 (1H, d, J=8.3 Hz), 8.31 (1H, d, J=2.4 Hz), 9.31 (1H, d, J=1.7 Hz), 12.52 (1H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; lithium hydroxide; In 1,4-dioxane; water; at 80℃; for 0.5h;Inert atmosphere; | General procedure: To a solution of 2-chloroheteroaryl compound 1 (0.50 mmol) in 1,4-dioxane (4.0 mL) were added pinacol boronate 3, 5, or 7 (0.60 mmol), Pd(OAc)2 (1.1 mg, 5.0 mumol), S-Phos (4.1 mg, 10.0 mumol), and 2 M LiOH solution (1.0 mL, 2.0 mmol) at room temperature, and the mixture was stirred for 30 min at 80 C under N2 atmosphere. The reaction was quenched by adding water, and then the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed in vacuo, and the residue was purified by silica-gel column chromatography. The solvent was removed in vacuo, and the residue was triturated with Et2O to give biaryl compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | With potassium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 150℃; for 0.666667h;Sealed vessel; | EXAMPLE 2143-[3-(3-furanyl)-1 /-/-pyrazolo[3,4-d]pyrimidin-4-yl]amino}-4-(4-hydroxy-1-piperidinyl)-//- methylbenzenesulfonamideTo a solution of 3-[(3-bromo-1 /-/-pyrazolo[3,4-d]pyrimidin-4-yl)amino]-4-(4-hydroxy- 1-piperidinyl)-/V-methylbenzenesulfonamide (145 mg, 0.30 mmol) and 2-(3-furanyl)- 4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane (61 mg, 0.31 mmol) in 1 ,4-dioxane (3.0 mL) and water (0.5 mL) was added K2C03 (125 mg, 0.90 mmol) and PdCI2(dppf CH2Cl2 (24.55 mg, 0.03 mmol) . The reaction vessel was sealed, heated at 150 C for 40 min, and concentrated. The residue was purified by flash column chromatography (3-7%MeOH/CHCIs) to afford the title compound (42.6 mg, 29%) as a light yellow solid. LCMS (ES) m/z 470 (M+H)+; 1H NMR (400 MHz, DMSO-d6) delta ppm 1.23 (d, J=4.29 Hz, 2 H) 1.49 (br. s, 2 H) 2.48 (d, J=5.05 Hz, 3 H) 2.59 (d, J=8.34 Hz, 3 H) 2.88 (br. s, 2 H) 4.58 (d, J=3.03 Hz, 1 H) 6.93 (s, 1 H) 7.34 - 7.43 (m, 1 H) 7.44 - 7.53 (m, 2 H) 7.92 (d, J=1.26 Hz, 1 H) 8.32 (s, 1 H) 8.45 - 8.56 (m, 2 H) 9.02 (d, J=2.02 Hz, 1 H) 13.97 (s, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | With potassium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 150℃; for 0.666667h;Sealed vessel; | EXAMPLE 2153-[3-(3-furanyl)-1 H-pyrazolo[3,4-d]pyrimidin-4-yl]amino}-4-(3-hydroxy-1-pipenmethylbenzenesulfonamideTo a solution of 3-[(3-bromo-1 /-/-pyrazolo[3,4-d]pyrimidin-4-yl)amino]-4-(3-hydroxy- 1-piperidinyl)-/V-methylbenzenesulfonamide (100 mg, 0.207 mmol) and 2-(2-furanyl)- 4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane (42.2 mg, 0.218 mmol) in 1 ,4-dioxane (2.0 mL) and water (0.5 mL) were added K2C03 (86 mg, 0.62 mmol) and PdCI2(dppf)«CH2Cl2 (16.9 mg, 0.02 mmol) . The reaction vessel was sealed, heated at 150 C for 40 min, and concentrated. The residue was purified by flash column chromatography (3-7%MeOH/CHCIs) to afford the title compound (21 .7 mg, 21 %) as a tan solid. LCMS (ES) m/z 470 (M+H)+; 1H N MR (400 MHz, DMSO-d6) delta ppm 1 .14 (br. s, 1 H) 1 .29 (d, J=13.89 Hz, 2 H) 1 .64 (br. s, 1 H) 1 .76 (br. s, 1 H) 2.28 - .37 (m, 1 H) 2.46 (d, J=4.80 Hz, 3 H) 2.67 (br. s, 1 H) 3.00 (br. s, 1 H) 3.15 (br. s, 1 H) 4.74 (d, J=4.55 Hz, 1 H) 6.77 - 6.86 (m, 1 H) 7.09 (d, J=3.28 Hz, 1 H) 7.35 (d, J=8.34 Hz, 1 H) 7.39 - 7.44 (m, 1 H) 7.53 (dd, J=8.46, 2.15 Hz, 1 H) 7.99 (s, 1 H) 8.45 (s, 1 H) 8.59 (d, J=2.02 Hz, 1 H) 9.05 (s, 1 H) 14.08 (s, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27% | With potassium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 150℃; for 0.666667h;Sealed vessel; | EXAMPLE 2123-[3-(3-furanyl)-1 H-pyrazolo[3,4-d]pyrimidin-4-yl]amino}-/V-methyl-4-(4- piperidinyl)benzenesulfonamideTo a solution of 3-[(3-bromo-1 /-/-pyrazolo[3,4-d]pyrimidin-4-yl)amino]-//-methyl-4- (4-methyl-1 -piperidinyl)benzenesulfonamide (200mg, 0.416 mmol), 2-(3-furanyl)-4, 4,5,5- tetramethyl-1 ,3,2-dioxaborolane (121 mg, 0.63 mmol) and K2C03 (288 mg, 2.08 mmol) in 1 ,4-dioxane (5 ml.) and water (1 mL) was added PdCI2(dppf)«CH2CI2 (34 mg, 0.04 mmol). The reaction vessel was sealed and heated at 150 C for 40 min. The reaction mixture was concentrated onto silica gel and purified by flash column chromatography (0-6% MeOH/CHCI3 containing 0.1 % NuEta3·Eta20) to afford a light yellow solid which was triturated with hot CH2CI2 to afford the title compound (55.8 mg, 27%) as a white solid. LCMS (ES) m/z 468 (M+H)+; 1 H NMR (400 MHz, DMSO-d6) delta ppm 0.73 - 0.82 (m, 2 H) 0.86 (d,J=6.57 Hz, 3 H) 1 .34 (br. s, 1 H) 1 .49 (br. s, 2 H) 2.47 - 2.49 (m, 3 H) 2.53 - 2.61 (m, 2 H) 2.86 (d, J=1 1 .37 Hz, 2 H) 6.96 (s, 1 H) 7.36 (d, J=8.34 Hz, 1 H) 7.44 - 7.52 (m, 2 H) 7.98 (t, J=1 .64 Hz, 1 H) 8.33 (s, 1 H) 8.46 (s, 1 H) 8.52 (s, 1 H) 9.03 (d, J=2.02 Hz, 1 H) 13.97 (s, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | With potassium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 150℃; for 0.666667h;Sealed vessel; | EXAMPLE 2133-[3-(3-furanyl)-1 /-/-pyrazolo[3,4-d]pyrimidin-4-yl]amino}-//-methyl-4-{4- [(methyloxy)methyl]-1 -piperidinyl}benzenesulfonamideTo a solution of 3-[(3-bromo-1 /-/-pyrazolo[3,4-d]pyrimidin-4-yl)amino]-//-methyl-4- {4-[(methyloxy)methyl]-1-piperidinyl}benzenesulfonamide (160 mg, 0.31 mmol) and 2-(3- furanyl)-4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane (72.9 mg, 0.376 mmol) in 1 ,4-dioxane (2.0 mL) and water (0.5 mL) were added K2C03 (130 mg, 0.939 mmol) andPdCI2(dppf)«CH2Ci2 (25.6 mg, 0.031 mmol) . The reaction vessel was sealed, heated at 150 C for 40 min, and concentrated. The residue was purified by flash column chromatography (3-7% MeOH/CHCI3) to afford a light yellow solid. The solid was washed with hot CH2CI2 to afford the title compound (52.4 mg, 34%) as a white solid. LCMS (ES) m/z 498 (M+H)+; 1 H NMR (400 MHz, DMSO-d6) delta ppm 0.78 (br. s, 2 H) 1.57 (br. s, 3 H) 2.48 (d, J=5.05 Hz, 3 H) 2.55 (br. s, 2 H) 2.90 (br. s, 2 H) 3.10 (d, J=6.32 Hz, 2 H) 3.23 - 3.31 (m, 3 H) 6.96 (s, 1 H) 7.34 - 7.42 (m, 1 H) 7.43 - 7.53 (m, 2 H) 7.99 (d, J=1 .26 Hz, 1 H) 8.33 (s, 1 H) 8.45 (s, 1 H) 8.51 (s, 1 H) 9.03 (d, J=2.02 Hz, 1 H) 13.97 (br. s, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium phosphate tribasic trihydrate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 90℃;Inert atmosphere; | N-{l-[5-bromo-7-(phenylsulfonyl)-7H-pyrrol^^D6 (450mg), 2-(3-furanyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane ( 240mg, 1.245mmol, commercially available from e.g. Maybridge, Sigma- Aldrich or Apollo), potassium phosphate trihydrate ( 660mg, 2.5mmol), palladium tetrakis ( 30mg, 0.026mmol) were dissolved in 1,4- dioxane ( 20ml) and water ( 4ml) and stirred under nitrogen at 90C ovemight. Cooled to room temperature, solvent removed in vacuo, water (150ml) was added extracted with EtOAc (3 x 1 0ml). The combined extracts were washed with brine and dried over MgSC>4, concentrated to give crude product which was purified by silica gel column eluting with pet eth/ EtOAc 1 : 1 to give 60mg of desired product D28. LCMS [MH+] 528.2 (at) 1.88min ( 5 min run) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,4-dioxane; for 4h;Reflux; | General procedure: Compound 6 (3.08 g, 8.0 mmol), phenylboronic acid (1.94 g, 16.0 mmol), and bis(triphenylphosphine)palladium(II)chloride (281 mg, 5 mol %) were dissolved in dioxane (50 mL), mixed with a Na2CO3 solution (12 mL, 2 M) and refluxed for 22 h. Liquid partition with AcOEt/H2O, dryness (Na2SO4) and concentration of the organic phase afforded 2.3 g (95%) of ethyl 3-(2-phenylnaphthalen-1-yl)propanoate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 90℃; for 12h;Inert atmosphere; | tert-butyl 4- furan-3-yl)benzoate. A mixture of 2-(furan-3-yl)-4,4,5,5-tetramethyl-l,3-dioxolane (379mg, 1.95 mmol), tert-butyl 4-bromobenzoate (500 mg, 1.95 mmol), sodium carbonate (621 mg, 5.86 mmol), tetrakis(triphenyl phosphine)palladium(O) (12 mg, 0.01 mmol) in a mixed solvent of 1 ,4-dioxane (16 ml) and water (4 ml) was stirred for 12 hours at 90°C under nitrogen atmosphere. After cooling to room temperature, the mixture was concentrated. The residue was purified by preparative-HPLC to give 2-a as a yellow oil (400 mg, 84percent). LRMS (M + H+) mlz: calcd 244.11; found 244. 1H NMR (300MHz, CD3OD): delta 8.02 (s, 1H), 7.95 (d, J= 8.1 Hz, 2H), 7.64 (d, J= 8.4 Hz, 2H), 7.60 (s, 1H), 6.87 (s, 1H), 1.61 (s, 9H). |
83% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 90℃;Inert atmosphere; | To a stirred solution of tert-butyl 4-bromobenzoate (1.934 g, 7.53 mmol) in dioxane (62 mL) under argon was added 2-(furan-3-yl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (1.464, 7.53 mmol), sodium carbonate (2.398g, 22.6 mmol) and distilled water (15.5 mL). The mixture was degassed with argon before addition of palladium tetrakis-triphenylphosphine (46.3 mg, 0.039 mmol). The reaction was heated at 90 °C overnight. The crude reaction mixture was poured onto water and extracted with EtOAc (3X). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by flash chromatography (10-20percent DCM in hexanes eluent) to provide tert-butyl 4-(furan-3-yl)benzoate (1.52g, 83percent yield) as a colorless oil. 1H NMR (300 MHz, Chloroform-d) delta 8.00 (d, J = 8.7 Hz, 2H), 7.82 (dd, J = 1.5, 0.9 Hz, 1H), 7.59 - 7.47 (m, 3H), 6.75 (dd, J = 1.9, 0.9 Hz, 1H), 1.62 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; water; at 110℃;Inert atmosphere; | General procedure: To 1,4-dioxane (15 mL) were added chloro-substituted N-heterocycles(10.0 mmol), aromatic boronic acid (or pinacol ester, 12.0 mmol), Pd(dppf)Cl2 (0.73 g, 1.0mmol) and aqueous Cs2CO3 (2 N, 10 mL, 20.0 mmol) under N2 atmosphere. The content washeated and kept at 110 °C overnight. The reaction mixture was cooled to room temperature after the completion of the reaction. Dioxane was removed under reduced pressure. The resultant aqueous solution was extracted with EtOAc. The combined organic phase was washed with water and saturated brine for three times, and dried over Na2SO4. After the removal of the solvent under reduced pressure, the residue was charged to flash chromatography, which gave the pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); In tetrahydrofuran; at 70℃; for 16h;Inert atmosphere; Sealed tube; | General procedure: In a glovebox, Cu(IPr)Cl catalyst and PMC (62.8 mg, 0.55 mmol,1.1 equiv) were charged to a glass reaction tube. A solution of 3(0.50 mmol) in THF (1.5 mL) was added, the tube was sealed, taken out of the glovebox, and heated at 70 C for 16 h. After cooling tor.t., H2O (2 mL) was added and the reaction mixture was acidified with aqueous HCl (1 M), and saturated with sodium chloride. After extraction with EtOAc (3 × 5 mL), the organic phase was dried overanhydrous sodium sulfate and concentrated under vacuo. The product was purified by silica gel column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13% | In N,N-dimethyl-formamide; at 20℃; for 14h; | General procedure: To a solution of 3-anisyl pinacol borane (50 mg, 0.21 mmol)in DMF (1 mL) was added N-bromosuccinimide (82 mg, 0.46 mmol). After stirring at room temperature for 14 h, resultant solution was treated with 10% Na2S2O3aq (10 ml) and was extracted with Et2O (10 ml3). The combined organic phase was washed with H2O (10 ml2) and brine (10 ml1) and dried over MgSO4. After removal of solvent under reduced pressure, the residue was chromatographed on silica gel with Hexane to afford 2-bromo-5-methoxyphenyl pinacol borate (57.3 mg, 87% yield) as colorless oil |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11% | With meso-tetra(p-tolyl)porphinato-palladium(II); potassium acetate; In 1,4-dioxane; at 110℃; for 15h; | General procedure: Aryl/heteroaryl bromide 1 (1 mmol), B2pin2(2), B2npg2(4) orBpin (6, 1.2 mmol), and dioxane (5 mL) are taken into a 25 mLround-bottomed flask. KOAc (2 mmol) was added and stirredthe resultant mixture at room temperature for 5 min, PdII-TpTP(0.15 mol%) was added, and the contents were refluxed on preheatedoil bath at 110 C under constant stirring in open-air.The reaction progress was ensured by TLC. After completion ofthe reaction, the mixture was cooled, dilute with water (20 mL)and extracted with tertbutylmethyl ether (3 × 10 mL). The combinedn-hexane layers were concentrated, and the crudeproduct obtained was purified by column chromatography (CC)on silica gel using a mixture of ethyl acetate and hexane (1:30)as eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13% | With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 14h; | General procedure: To a solution of 3-anisyl pinacol borane (50mg, 0.21mmol) in DMF (1mL) was added N-bromosuccinimide (82mg, 0.46mmol). After stirring at room temperature for 14h, resultant solution was treated with 10% Na2S2O3 aq (10 ml) and was extracted with Et2O (10ml×3). The combined organic phase was washed with H2O (10ml×2) and brine (10ml×1) and dried over MgSO4. After removal of solvent under reduced pressure, the residue was chromatographed on silica gel with Hexane to afford 2-bromo-5-methoxyphenyl pinacol borate (57.3mg, 87% yield) as colorless oil |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With N-chloro-succinimide; In N,N-dimethyl-formamide; at 100℃; for 14h; | General procedure: To a solution of 3-anisyl pinacol borane (50mg, 0.21mmol) in DMF (1mL) was added N-bromosuccinimide (82mg, 0.46mmol). After stirring at room temperature for 14h, resultant solution was treated with 10% Na2S2O3 aq (10 ml) and was extracted with Et2O (10ml×3). The combined organic phase was washed with H2O (10ml×2) and brine (10ml×1) and dried over MgSO4. After removal of solvent under reduced pressure, the residue was chromatographed on silica gel with Hexane to afford 2-bromo-5-methoxyphenyl pinacol borate (57.3mg, 87% yield) as colorless oil |
37% | With N-chloro-succinimide; In N,N-dimethyl-formamide; at 100℃; for 2h; | To a solution of <strong>[248924-59-6]2-(furan-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane</strong> (1g, 5.10 mmol) in DMF (15 mL) was added NCS (1.50 g, 11.21 mmo1). The mixture wasstirred at 100 oc for 2h. The resultant solution was treated with aq 10% Na2S203 (50 mL) and was extracted with MTBE (50 mL x 3). The combined organic phase was washed withbrine ( 100 mL) and dried over Na2S04. After removal of solvent under reduced pressure, theresidue was purified by flash silica gel chromatography (ISCO; 12 g SepaFlash SilicaFlash Column, Eluent of 0~10%) Ethyl acetate/Petroleum ethergradient 20mL/min).Compound 36A (0.5 g, :yield: 37.0%) was obtained as a yellow oil. 1H NMR (400MHz,CDCh) 8 6.45- 6.23 (m, 1H), 1.31 (s, 12H). |
37% | With N-chloro-succinimide; In N,N-dimethyl-formamide; at 100℃; for 2h; | To a solution of 2-(furan-3-yl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (1 g, 5.10 mmol) in DMF (15 mL) was added NCS (1.50 g, 11.21 mmol). The mixture was stirred at 100 C for 2h. The resultant solution was treated with aq 10% Na2S203 (50 mL) and was extracted with MTBE (50 mL x 3). The combined organic phase was washed with brine (100 mL) and dried over Na2S04. After removal of solvent under reduced pressure, the residue was purified by flash silica gel chromatography (ISCO; 12 g SepaFlash Silica Flash Column, Eluent of 0-10% Ethyl acetate/Petroleum ethergradient 20mL/min). Compound 36A (0.5 g, yield: 37.0%) was obtained as a yellow oil. 1H NMR (400MHz, CDCl3) d 6.45 - 6.23 (m, 1H), 1.31 (s, 12H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
17%Chromat. | With palladium diacetate; triphenylphosphine; p-benzoquinone; In N,N-dimethyl-formamide; at 65℃; for 0.0833333h;Inert atmosphere; | General procedure: A mixture of 3g (5.0 mg, 19 mumol), Pd(OAc)2 (4.2 mg, 19 mumol), PPh3 (10 mg, 38 mumol), and p-benzoquinone (2.0 mg, 19 mumol) was placed in 5.0 mL vial and dissolved in DMF (400 muL)-MeOH (400 muL) or MeOH (800 muL). Then [11C]O gas was passed through the vial with a stream of helium (2 mL/min) and the mixture was heated at 65 C for 5 min. Part of the resulting mixture was purified by high-performance liquid chromatography (HPLC) and the RCY of the fraction was determined by a NaI(Tl) well-type scintillation detector system. Products were identified by comparison their retention times with those of the authentic samples. The detail HPLC conditions of each compound were provided in the supplemental materials. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,4-dioxane; water; at 85℃; for 3h;Inert atmosphere; | Methyl 4-[(4-bromophenyl)sulfonyl]amino}-2,6-difluorobenzoate (150 mg, 0.372 mmol) was dissolved in 1,4-dioxane (15 ml), and <strong>[248924-59-6]2-(furan-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane</strong> (158 mg, 0.814 mmol), [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (27.0 mg, 40.0 mumol), and a 1 M aqueous sodium carbonate solution (5.0 ml) were added thereto. This solution was degassed under reduced pressure, and purged with argon gas, followed by stirring at 85 C. for 3 hours. After the stirring, the solvent was removed by distillation, and the obtained residue was suspended in methanol (3.0 ml). The suspension was filtered, and the solvent was removed by distillation from the obtained residue. To this residue, tetrahydrofuran (4.0 ml), water (1.0 ml), and a 2 N aqueous sodium hydroxide solution (2.0 ml) were added, followed by stirring at 60 C. for 3 hours. After the reaction liquid was concentrated, purification was conducted by reversed-phase HPLC (H2O containing 0.1% TFA/CH3CN system) to obtain the title compound (100 mg, 0.264 mmol, 71%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; N,N-dimethyl-formamide; at 80℃; for 18h;Inert atmosphere; Sealed tube; | Example 23A(6aS,7S, 1 0a5-4-(3-furyl)-2,7-dimethyl- lOa-phenyl-5,6a,7,9, 10, lOahexahydrobenzo[h]quinazolin-8(61])-one In a pressure tube, the product from Example 13D (0.35 g, 1.0 mmol), 2-(furan-3-yl)- 4,4,5,5 -tetramethyl- 1,3 ,2-dioxaborolane (0.20 g, 1.0 mmol), tetrakis(triphenylphosphine)palladium(0) (0.06 g, 0.05 mmol) and 2 M sodium carbonate (1.5 mL, 3.1 mmol) were combined in dioxane (7 mL) and dimethylformamide (1.3 mL). The mixture was sparged with nitrogen for 15 minutes. The pressure tube was sealed and heated to 80 C for 18 hours. The reaction was diluted with ethyl acetate and washed with water.The aqueous layer was back extracted with ethyl acetate. The combined ethyl acetate layers were washed with saturated sodium chloride, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with 20% ethyl acetate in heptane to the titled compound (0.34 g, 89%). ?H NMR (400 MHz, CDC13) ppm 1.16 (d, J=6.72 Hz, 3 H) 2.00 - 2.17 (m, 3 H) 2.27 -2.39 (m,1 H) 2.50 - 2.59 (m, 2 H) 2.64 (dd, J=1 1.66, 6.67 Hz, 1 H) 2.68 (s, 3 H) 2.78 (dt, J16.83,5.73 Hz, 1 H) 2.93 - 3.04 (m, 1 H) 3.25 (ddd, J=14.23, 6.04, 4.34 Hz, 1 H) 6.96 (s, 1 H) 7.22(d, J=7.26 Hz, 1 H) 7.25 - 7.31 (m, 2 H) 7.43 (d, J=7.81 Hz, 2 H) 7.51 (s, 1 H) 7.86 (s, 1 H);MS (ESI) m/z 373.2 (M+H). |
89% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; N,N-dimethyl-formamide; at 80℃; for 18.25h;Inert atmosphere; Sealed tube; | In a pressure tube, the product from Example 13D (0.35 g, 1.0 mmol), <strong>[248924-59-6]2-(furan-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane</strong> (0.20 g, 1.0 mmol), tetrakis(triphenylphosphine)palladium(0) (0.06 g, 0.05 mmol) and 2 M sodium carbonate (1.5 mL, 3.1 mmol) were combined in dioxane (7 mL) and dimethylformamide (1.3 mL). The mixture was sparged with nitrogen for 15 minutes. The pressure tube was sealed and heated to 80 C. for 18 hours. The reaction was diluted with ethyl acetate and washed with water. The aqueous layer was back extracted with ethyl acetate. The combined ethyl acetate layers were washed with saturated sodium chloride, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with 20% ethyl acetate in heptane to the titled compound (0.34 g, 89%). 1H NMR (400 MHz, CDCl3) delta ppm 1.16 (d, J=6.72 Hz, 3H) 2.00-2.17 (m, 3H) 2.27-2.39 (m, 1H) 2.50-2.59 (m, 2H) 2.64 (dd, J=11.66, 6.67 Hz, 1H) 2.68 (s, 3H) 2.78 (dt, J=16.83, 5.73 Hz, 1H) 2.93-3.04 (m, 1H) 3.25 (ddd, J=14.23, 6.04, 4.34 Hz, 1H) 6.96 (s, 1H) 7.22 (d, J=7.26 Hz, 1H) 7.25-7.31 (m, 2H) 7.43 (d, J=7.81 Hz, 2H) 7.51 (s, 1H) 7.86 (s, 1H); MS (ESI) m/z 373.2 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43 mg | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,4-dioxane; water; at 140℃; for 0.75h;Microwave irradiation; Inert atmosphere; | Sodium carbonate (38 mg, 0.36 mmol) in water (1 mL) was added to a mixture of N-(2-hydroxy-4-methyl-6-quinolyl)-5-iodo-2-morpholino-benzamide (60 mg, 0.12 mmol) and 2-(3-furyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (50 mg, 0.24 mmol) in 1,4-dioxane (5 mL) in 10 mL microwave vial and purged with argon before Pd(dppf)C12 (9 mg, 0.012 mmol) was added. Reaction was then stirred in microwave reactor at 140C for 45 min.Mixture was diluted with DCM and water and product precipitated. Water layer was decanted and organic layer filtered off. The obtained precipitate was washed with DCM and water and dried to give 43 mg of pure product 5- (3-furyl)-N-(2-hydroxy-4-methyl-6-quinolyl)-2-morpholino-benzamide (compound- 167).MS: m/z (M+H)+ 430.06, purity 99% 1H NMR (300 MHz, DMSC /6) delta 11.60 (s, 1H), 11.16 (s, 1H), 8.33 (d, J= 2.3 Hz, 1H), 8.28 - 8.17 (m, 1H), 7.95 (t, J= 2.1 Hz, 1H), 7.82 (dd, J= 9.0, 2.4 Hz, 1H), 7.77 - 7.69 (m, 2H), 7.40 - 7.25 (m, 2H), 6.99 (t, J= 1.8 Hz, 1H), 6.44 (s, 1H), 3.82 - 3.61 (m, 4H), 3.09 - 2.92 (m, 4H), 2.46 - 2.35 (m, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; at 100℃; for 16h; | Preparation of 5 -(furan-3-yl)-2-morpholino nicotinic acid (2): a suspension of 5- bromo-2-morpholinonicotinic acid (1) (1.0 g, 3.49 mmol, 1 eq), 2-(furan-3-yl)-4,4,5,5- tetramethyl-l,3,2-dioxaborolane (1A) (1.36 g, 6.99 mmol, 2 eq), Na2C03 (1.48 g, 13.98mmol, 4 eq) in Dioxane (20 mL) was degassed for 10 min. Then added Pd(PPh3)4 (404 mg, 0.34 mmol, 0.1 eq) and stirred at 100 C for 16 h. After completion, the solvent was evaporated, the residue was taken in water and extracted with EtOAc (3 x 30 mL). The combined extracts were washed with water (60 mL), brine (60 mL), dried over anhydrous Na2S04, filtered and evaporated. The crude compound was purified by column chromatography (Si02) by using MeOH: DCM (10: 90) to afford 5-(furan-3-yl)- 2-morpholinonicotinic acid (2) (500 mg, 51 %) as yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 80℃; for 16h; | Preparation of 5-(furan-3-yl)-N-(2-hydroxy-4, 8-dimethylquinolin-6-yl)-2- morpholinonicotinamide (compound- 179): to a solution of 5-bromo-N-(2-hydroxy-4,8- dimethylquinolin-6-yl)-2-morpho lino nicotinamide (2) (115 mg, 0.251 mmol, 1 eq) in Dioxane: H20 (2: 1) (10 vol) was added 2A (97.3 mg, 0.502 mmol, 2 eq) and Na2C03 (79.81 mg, 0.753 mmol, 3 eq) and degassed the mixture for 15 mins. Then added Pd(PPh3)4 (28.9 mg, 0.025 mmol, 0.1 eq) heated at 80 C for 16 h. After completion, the reaction mixture was poured into ice water and extracted with EtOAc (2 x 30 mL). The combined extracts were washed with water (40 mL), brine (40 mL), dried over anhydrous Na2S04, filtered and evaporated. The crude compound was purified by column chromatography (Si02) using MeOH: DCM (3: 97) to afford 5-(furan-3-yl)-N- (2-hydroxy-4, 8-dimethylquinolin-6-yl)-2-morpholinonicotinamide (compound- 179) (50 mg, 45 %) as off white solid. 1H NMR (400 MHz, DMSO- 6): delta 10.74 (s, 1H), 10.56 (s, 1H), 8.60 (d, J = 2.0 Hz, 1H), 8.24 (s, 1H), 8.06 (d, J = 2.4 Hz, 2H), 7.76 (t, J = 1.7 Hz, 1H), 7.69 (d, J = 1.5 Hz, 1H), 7.04 (s, 1H), 6.46 (s, 1H), 3.70 - 3.60 (m, 4H), 3.31 - 3.27 (m, 4H), 2.44 (s, 3H), 2.41 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 100℃; for 1h;Microwave irradiation; | Example 51 Preparation of 3-(3-furyl)-17-methylmorphinan (51), hydrochloride salt 17-Methylmorphinan-3-yl trifluoromethanesulfonate [Neumeyer et al. (2012) J Med Chem 55(8):3878-3890 and Zhang et al. (2004) J Med Chem 47(1): 165-174] (145 mg, 0.372 mmol), 3-furanboronic acid pinacol ester (117.7 mg, 0.594 mmol), and sodium carbonate (126 mg, 1.189 mmol) were placed in a microwave reaction tube. Dioxane (2 mL) and water (1 mL) were added to the tube and the mixture was degassed for five minutes before tetrakis(triphenylphosphine)palladium(0) (83.5 mg, 0.072 mmol) was added. The mixture was degassed and was irradiated in a microwave for one hour at 100 C. The mixture was cooled to room temperature, and partitioned between with dichloromethane (50 mL) and water (10 mL). Brine (30 mL) was added. The organic solution was separated and the aqueous solution was extracted with dichloromethane (25 mL). The combined organic solution was dried over anhydrous sodium sulfate, was filtered and was concentrated. The residue was purified by flash column chromatography on silica gel to afford the product (51) (75.5 mg) as the free base in 66% yield. lU NMR (500 MHz, Chloroform-c/) delta 7.69 - 7.65 (m, 1H), 7.44 (t J = 1.7 Hz, 1H), 7.33 (d, J = 1.8 Hz, 1H), 7.22 (dd, J= 7.9, 1.8 Hz, 1H), 7.09 (d, J= 7.9 Hz, 1H), 6.66 (dd, J= 1.8, 0.9 Hz, 1H), 3.02 (d, J = 18.5 Hz, 1H), 2.84 - 2.79 (m, 1H), 2.63 (dd, J = 18.5, 5.8 Hz, 1H), 2.45 - 2.42 (m, 2H), 2.39 (s, 3H), 2.08 (td, J = 12.4, 3.3 Hz, 1H), 1.88 - 1.82 (m, 1H), 1.78 - 1.70 (m, 1H), 1.56 - 1.48 (m, 1H), 1.45 - 1.21 (m, 6H), 1.12 (qd, J= 12.6, 3.9 Hz, 1H). MS for C2iH25NO, 308 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42.5% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 100℃; for 2h;Microwave irradiation; Inert atmosphere; | Example 106 Preparation of (4bR,8aR,9R)-3-(furan-3-yl)-ll-(2-(2-methoxyethoxy)ethyl)- 6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene (106) (4bR,8aR,9R)-l l-(2-(2-Methoxyethoxy)ethyl)-6,7,8,8a,9,10-hexahydro-5H- 9,4b-(epiminoethano)phenanthren-3-yl trifluoromethanesulfonate (92.6 mg, 0.194 mmol), 2- (furan-3-yl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (56.4 mg, 0.291 mmol) and sodium carbonate (61.7 mg, 0.582 mmol) were placed in a microwave reaction tube. Dioxane (2 mL) and water (0.5 mL) were added to the tube. The mixture was degassed for five minutes under nitrogen. Tetrakis(triphenylphosphine)palladium(0) (44.8 mg, 0.039 mmol) was added to the mixture and the reaction was irradiated in a microwave for two hours at 100 C. The solvent was removed via lyophilization. The residue was dissolved in dichloromethane and washed with brine. The organic layer was dried over sodium sulfate, was filtered and was concentrated. After purification by chromatography on silica gel using a Biotage instrument, (4bR,8aR,9R)-3-(furan-3-yl)-l l-(2-(2-methoxyethoxy)ethyl)-6,7,8,8a,9,10-hexahydro-5H- 9,4b-(epiminoethano)phenanthrene (106) (32.6 mg, 0.082 mmol, 42.5 % yield) was obtained as an off-white semi solid. MS (EI) for C25H33NO3: 396.2 (MH+).1H NMR (500 MHz, Methanol-d4) delta 7.85 (d, J = 1.5 Hz, 1H), 7.54 (t, J = 1.7 Hz, 1H), 7.46 - 7.42 (m, 1H), 7.32 (dd, J = 7.9, 1.8 Hz, 1H), 7.15 (d, J = 7.9 Hz, 1H), 6.79 - 6.75 (m, 1H), 3.70 - 3.53 (m, 6H), 3.36 (d, J = 23.2 Hz, 4H), 3.11 - 3.00 (m, 2H), 2.85 (dt, J = 12.3, 5.9 Hz, 1H), 2.81 - 2.69 (m, 2H), 2.66 - 2.51 (m, 2H), 2.19 (td, J = 12.6, 3.3 Hz, 1H), 1.90 (dt, J = 13.1, 3.0 Hz, 1H), 1.79 (td, J = 12.9, 4.7 Hz, 1H), 1.74 - 1.65 (m, 1H), 1.58 (dt, J = 10.9, 2.9 Hz, 1H), 1.51 - 1.25 (m, 6H), 1.17 (qd, J = 13.6, 12.9, 3.6 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With palladium diacetate; potassium carbonate; ruphos; In 1,4-dioxane; water; at 80℃;Inert atmosphere; | General procedure: A 40 mL scintillation vial containing a stir bar was charged with the 5-p-toluenesulfonyltetrazole substrate (1 equiv), arylboronic acid (1.3 equiv), potassium carbonate (3 equiv), palladium (II) acetate (3 mol%), and dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine (?RuPhos,? 4 mol%). The vial was capped and was evacuated and backfilled with N2 (2x), and then dioxane (2.0 mL) was added. The mixture was allowed to stir at room temperature for a few minutes before water (0.5 mL) was added. The resulting mixture was heated under an atmosphere of N2 in an 80 C oil bath. Upon completion of the reaction (asjudged by TLC or LC-MS analysis), the reaction was allowed to cool and was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc, and the combined organics were concentrated under reduced pressure. The crude material thus obtained was purified by silica gel chromatography to afford the desired product. In the case of molar polar final products, purification was conducted by reverse-phase HPLC. In certain cases, the use of sodium bicarbonate (NaHCO3) as base instead of potassium carbonate (K2CO3) was found to be advantageous; these instances are denoted below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45.6% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In N,N-dimethyl-formamide; at 125℃; for 0.25h;Microwave irradiation; | To a 0.5-2 ml microwave tube was added (S)-N-((1-(1-(4-bromophenyl)-1H-imidazol-2-yl)-2-phenylethyl)carbamoyl)-2-methylbenzenesulfonamide (20 mg, 0.037 mmol), <strong>[248924-59-6]2-(furan-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane</strong> (10.79 mg, 0.056 mmol), Tetrakis(triphenylphosphine)palladium(0) (4.28 mg, 3.71 mumol), followed by DMF (1 mL), 2M K2CO3 solution (50 muL, 0.100 mmol). The reaction mixture was heated in a microwave reactor at 125 C. for 15 mins. The reaction mixture was filtered and the filtrate was purified by PrepHPLC to afford (8.9 mg, 45.6%) of the title compound. 1H NMR (500 MHz, DMSO-d6) delta 8.25 (s, 1H), 7.85-7.74 (m, 2H), 7.57 (d, J=8.1 Hz, 2H), 7.45 (br. s., 1H), 7.37-7.26 (m, 2H), 7.22-7.04 (m, 5H), 7.00 (s, 1H), 6.94 (d, J=8.1 Hz, 2H), 6.71 (d, J=7.0 Hz, 2H), 4.78 (d, J=5.9 Hz, 1H), 3.02-2.77 (m, 2H), 2.53 (m, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In methanol; toluene;Inert atmosphere; Reflux; | General procedure: <strong>[1458-01-1]Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate</strong> 2 (1 eq.) was combined with K2CO3 (10 eq.), the appropriate (het)aryl boronic acid (1.5 eq.) and Pd(PPh3)4 (5 mol%) in a two-neck round bottom flask. The flask was connected to a condenser and purged with nitrogen. A 4:1 mixture of anhydrous toluene: MeOH (60 mL) was added via syringe and the reaction mixture was heated at reflux for 0.5-18 h. The mixture was allowed to cool to room temperature and filtered through Celite (10 x 3 cm, eluting with 3 x 20 mL EtOAc). The filtrate was evaporated to dryness and the residue purified by silica gel flash column chromatography using EtOAc/pet spirit. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31%Spectr.; 11%Spectr.; 5%Spectr.; 5%Spectr. | With Fe(1,2-bis(dimethylphosphino)ethane)2Cl2; sodium 2-ethylhexanoic acid; In tetrahydrofuran; at 60℃; for 48h;Inert atmosphere; Schlenk technique; Irradiation; Glovebox; | General procedure: In an argon-filled glovebox, dmpe2FeCl2 1 (8.6 mg, 0.02 mmol), sodium 2-ethylhexanoate (6.6 mg,0.04 mmol), HBpin (87 L, 0.6 mmol), substrate (0.5 mmol), and THF (1 mL) were added to a 1.7 mL sample vial and shaken to ensure full dissolution. The vial was placed under blue light radiation for 48 h and then allowed to cool to room temperature. Yields determined by 1H-NMR spectroscopy ofthe crude reaction mixtures using 1,3,5-trimethoxybenzene as an internal standard [0.5 mL; standard solution = 1,3,5-trimethoxybenzene (0.336 g, 2.0 mmol) in diethyl ether (10 mL)]. Product ratios were determined by 1H-NMR spectroscopy of the crude reaction mixtures. |
Tags: 248924-59-6 synthesis path| 248924-59-6 SDS| 248924-59-6 COA| 248924-59-6 purity| 248924-59-6 application| 248924-59-6 NMR| 248924-59-6 COA| 248924-59-6 structure
[ 796851-30-4 ]
2-(Benzofuran-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Similarity: 0.84
[ 1192755-14-8 ]
2-(Benzofuran-7-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Similarity: 0.84
[ 864776-02-3 ]
4,4,5,5-Tetramethyl-2-(2-methylfuran-3-yl)-1,3,2-dioxaborolane
Similarity: 0.81
[ 519054-55-8 ]
2-(Benzofuran-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Similarity: 0.79
[ 934329-77-8 ]
2-(Benzofuran-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Similarity: 0.79
[ 864776-02-3 ]
4,4,5,5-Tetramethyl-2-(2-methylfuran-3-yl)-1,3,2-dioxaborolane
Similarity: 0.81
[ 1025718-96-0 ]
2-(2,5-Dimethylfuran-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Similarity: 0.78
[ 846023-58-3 ]
4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carbaldehyde
Similarity: 0.76
[ 1055881-23-6 ]
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carbaldehyde
Similarity: 0.73
[ 374790-93-9 ]
2-(2-Furanyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Similarity: 0.71
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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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