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CAS No. : | 75927-49-0 | MDL No. : | MFCD00192492 |
Formula : | C8H15BO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DPGSPRJLAZGUBQ-UHFFFAOYSA-N |
M.W : | 154.01 | Pubchem ID : | 5233012 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.75 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 47.04 |
TPSA : | 18.46 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.78 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 2.06 |
Log Po/w (WLOGP) : | 1.8 |
Log Po/w (MLOGP) : | 0.76 |
Log Po/w (SILICOS-IT) : | 0.92 |
Consensus Log Po/w : | 1.11 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.03 |
Solubility : | 1.45 mg/ml ; 0.0094 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.08 |
Solubility : | 1.29 mg/ml ; 0.00838 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.91 |
Solubility : | 1.9 mg/ml ; 0.0123 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.05 |
Signal Word: | Danger | Class: | 3 |
Precautionary Statements: | P210-P240-P241-P242-P243-P261-P264-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P312-P363-P370+P378-P403+P233-P501 | UN#: | 3272 |
Hazard Statements: | H225-H315-H319-H335 | Packing Group: | Ⅲ |
GHS Pictogram: |
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* 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 |
---|---|---|
252 g | at 85 - 90℃; Inert atmosphere | Under a nitrogen atmosphere, 193 g of pinacol and 14 g of 2,6-di-t-butyl-4-methylphenol were charged in a 1 L reaction flask,To 85-90 ° C, until the pinacol is completely melted, the slow trickle-down of the intermediate reaction, attention to control the dropping rate, then atmospheric steamDistillation device, the reaction of diisopropylamine separation, after the end of the reaction temperature to obtain colorless transparent liquid vinyl boronic acid which252 g of the alcohol ester, and GC: 99.1percent (excluding the polymerization inhibitor). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
palladium diacetate; In diethyl ether; | Step 1: Preparation of compound 12, To a solution of 4,4,5, 5-tetramethyl-2-vinyl- 1,3,2-dioxaborolane (0.31 g} 2.0 mmol) and PdOAc2 (4.5 mg, 0.02 mmol) in anhydrous Ether (3 mL) was added a solution of ethyl 2-diazoacetate (0,57 g, 5.0 mmol) in ether (2 mL) dropwise under N2. During the halfway of the addition, additional PdOAc2 (4.49 mg, 0.02 mmoi) was added. When N2 evolution had ceased, the reaction mixture was filtered through activated neutral aluminum oxide and washed with ether. The filtrate was concentrated to yield compound 12 (0.50 g, 2.0 mmol) as a yellow oil. The crude product was used without further purification. | |
palladium diacetate; In diethyl ether;Inert atmosphere; | To a solution of 4,4,5,5-tetramethyl-2-vinyl- 1,3,2-dioxaborolane (0.31 g, 2.0 mmol) and PdOAc2 (4.5 mg, 0.02 mmol) in anhydrous Ether (3 mL) was added a solution of ethyl 2-diazoacetate (0.57 g, 5.0 mmol) in ether (2 mL) dropwise under N2. During the halfway of the addition, additional PdOAc2 (4.49 mg, 0.02 mmol) was added. When 2 evolution had ceased, the reaction mixture was filtered through activated neutral aluminum oxide and washed with ether. The filtrate was concentrated to yield compound 12 (0.50 g, 2.0 mmol) as a yellow oil. The crude product was used without further purification. | |
With palladium diacetate; In diethyl ether; at 20.0℃; for 1.33333h; | To a solution of 2-ethenyl-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (10.0 g, 4.38 mmol) and palladium acetate (166 mg, 0.44 mmol) in ether (50 mL) was added ethyl 2-diazoacetate (6.60 g, 5.47mmol) in ether (20 mL) dropwise for 10 min at room temperature. Palladium acetate (166 mg, 0.44 mmol) and ethyl 2-diazoacetate (6.60 g, 5.47 mmol) in ether (20 mL) were again added dropwise for another 10 min. The resulting solution was then stirred for 1 h at room temperature. After filtration through active aluminum oxide, the filtrate was concentrated in vacuo to afford ethyl 2-(tetramethyl- l,3,2-dioxaborolan-2-yl)cyclopropane-l-carboxylate as yellow oil (24.0 g). The crude product was used in the next step without further purification. . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With triethylamine;bis(tri-t-butylphosphine)palladium(0); In toluene; at 80℃; for 2h;Inert atmosphere; Autoclave; Microwave irradiation; | Exampel A51. Synthesis of (lR.2S)-(E)-5'-methoxy-2-(3-(4-(2-morpholinoethvnstyryl)- l Eta-indazol-6-yl)spiro[cyclopropane-K3'-indolinl-2'-one 2.2.2-trifluoroacetateA . (E)-4- (4- (2-(4, 4, 5, 5-tetramethyl-l, 3, 2-dioxaborolan-2-yl)vinyl) phenethyl)morpholineTo a mixture of <strong>[736991-39-2]4-(4-bromophenethyl)morpholine</strong> (731 mg, 2.71 mmol) and4,4,5, 5-tetramethyl-2-vinyl-l ,3,2-dioxaborolane (0.5 mL, 2.95 mmol, 1.1 eq.) and toluene (10 mL) in a 20 mL microwave vial was added Et3N (0.76 mL, 5.4 mmol, 2 eq.), followed by Pd(P'Bu3)2 (14 mg, 0.027 mmol, 1 mol%). The resulting mixture was purged with argon, then capped and heated at 80 0C (oil temp.) for 2 h. After cooling to rt, it was quenched with sat. NaHCO3 (10 mL), H2O (10 niL), extracted with EtOAc (30 mL x 2) and dried (Na2SO4). After evaporation of the solvents, the residue was purified by Biotage column system (EtOAc/hex gradient: 0-100%) to give (E)-4-(4-(2-(4,4,5,5- tetramethyl-l ,3,2-dioxaborolan-2-yl)vinyl)phenethyl)mophiholine as a white solid (714 5 mg, 77%). 1 H NMR (400 MHz, CDCl3) delta 7.42 (d, J = 8.0 Hz, 2H), 7.38 (d, J = 19.0 Hz, I H), 7.19 (d, J = 7.8 Hz, 2H), 6.13 (d, J = 18.3 Hz, I H), 3.75 (t, J = 4.4 Hz, 4H), 2.84- 2.77 (m, 2H), 2.63-2.56 (m, 2H), 2.53 (br, pseudo s, 4H), 1.32 (s, 12H). |
77% | With triethylamine;bis(tri-t-butylphosphine)palladium(0); In toluene; at 80℃; for 2h;Inert atmosphere; Microwave irradiation; | A. (E)-4-(4-(2-(4, 4, 5, 5-tetramethyl-l, 3,2-dioxaborolan-2-yl)vinyl) phenethyl)morpholine[00197] To a mixture of <strong>[736991-39-2]4-(4-bromophenethyl)morpholine</strong> (731 mg, 2.71 mmol) and 4,4,5,5-tetramethyl-2-vinyl-l,3,2-dioxaborolane (0.5 mL, 2.95 mmol, 1.1 eq.) and toluene (10 mL) in a 20 mL microwave vial was added Et3N (0.76 mL, 5.4 mmol, 2 eq.), followed by Pd(P'Bu3)2 (14 mg, 0.027 mmol, 1 mol%). The resulting mixture was purged with argon, then capped and heated at 80 C (oil temp.) for 2 h. After cooling to rt, it was quenched with sat. NaHC03 (10 mL), H20 (10 mL), extracted with EtOAc (30 mL x 2) and dried(Na2SC>4). After evaporation of the solvents, the residue was purified by Biotage column system (EtOAc hex gradient: 0-100%) to give (E)-4-(4-(2-(4,4,5,5-tetramethyl- 1,3,2- dioxaborolan-2-yl)vinyl)phenethyl)mo holine as a white solid (714 mg, 77%). NMR (400 MHz, CDC13) delta 7.42 (d, J = 8.0 Hz, 2H), 7.38 (d, J = 19.0 Hz, 1H), 7.19 (d, J = 7.8 Hz, 2H), 6.13 (d, J = 18.3 Hz, 1 H), 3.75 (t, J = 4.4 Hz, 4H), 2.84-2.77 (m, 2H), 2.63-2.56 (m, 2H), 2.53 (br, pseudo s, 4H), 1.32 (s, 12H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With triethylamine;bis(tri-t-butylphosphine)palladium(0); In toluene; at 80℃; for 2h;Inert atmosphere; Microwave irradiation; | Synthesis of (E)-4-("4-(2-(4.4.5,5-tetramethyl-L3,2-dioxaborolan-2-yl)vinyl)benzyl) morpholine[00124] The title compound (4.35 g, 71 %) was obtained as a white to yellow solid from <strong>[132833-51-3]4-(4-bromobenzyl)morpholine</strong> (4.18 g, 16.3 mmol) and 4,4,5,5-tetramethyl-2-vinyl- 1 ,3,2- dioxaborolane (3 mL, 17.7 mmol, 1.1 eq.) using the method for the preparation of Example A51A (PhCH3 = 30 mL, 1 mol% Pd(P,Bu3)2, 80 C, 1 h). NMR (400 MHz, CDC13) delta 7.45 (d, J = 8.0 Hz, 2H), 7.40 (d, J = 18.4 Hz, 1H), 7.31 (d, J = 8.0 Hz, 2H), 6.16 (d, J = 18.0 Hz, 1H), 3.72 (t, J = 4.4 Hz, 4H), 3.50 (s, 2H), 2.47-2.42 (m, 4H), 1.32 (s, 12H); MS ESI 330.1 [M + H]+, calcd for [C19H28BN03 + H]+ 330.2.; Example A51. Synthesis of 1Kappa.25 -(Epsilon)-5'^6^omicronchinu-2-(3-(4-(2^omicron ^1etaomicron6Phinu1 5GammanuGammanu1 -1Eta- indazol-6-yl)spiro[cyclopropane- 1 ,3'-indolinl-2'-one 2,2,2-trifluoroacetateA. (E)-4-(4-(2-(4, 4, 5, 5-tetramethyl-l, 3,2-dioxaborolan-2-yl)vinyl) phenethyl)morpholine[00197] To a mixture of 4-(4-bromophenethyl)morpholine (731 mg, 2.71 mmol) and 4,4,5,5-tetramethyl-2-vinyl-l,3,2-dioxaborolane (0.5 mL, 2.95 mmol, 1.1 eq.) and toluene (10 mL) in a 20 mL microwave vial was added Et3N (0.76 mL, 5.4 mmol, 2 eq.), followed by Pd(P'Bu3)2 (14 mg, 0.027 mmol, 1 mol%). The resulting mixture was purged with argon, then capped and heated at 80 C (oil temp.) for 2 h. After cooling to rt, it was quenched with sat. NaHC03 (10 mL), H20 (10 mL), extracted with EtOAc (30 mL x 2) and dried(Na2SC>4). After evaporation of the solvents, the residue was purified by Biotage column system (EtOAc hex gradient: 0-100%) to give (E)-4-(4-(2-(4,4,5,5-tetramethyl- 1,3,2- dioxaborolan-2-yl)vinyl)phenethyl)mo holine as a white solid (714 mg, 77%). NMR (400 MHz, CDC13) delta 7.42 (d, J = 8.0 Hz, 2H), 7.38 (d, J = 19.0 Hz, 1H), 7.19 (d, J = 7.8 Hz, 2H), 6.13 (d, J = 18.3 Hz, 1 H), 3.75 (t, J = 4.4 Hz, 4H), 2.84-2.77 (m, 2H), 2.63-2.56 (m, 2H), 2.53 (br, pseudo s, 4H), 1.32 (s, 12H). |
With bis(tri-t-butylphosphine)palladium(0); N-ethyl-N,N-diisopropylamine; In toluene; for 3h;Inert atmosphere; Heating; | General procedure: Bromoaryl derivatives (5mmol, 1.0 equiv), pinacol vinylboronate (6mmol, 1.2 equiv) and DIEA (20mmol, 2.0 equiv) were dissolved in toluene (10mL), then air was immediately replaced 5 times with nitrogen after the addition of bis(tri-tert-butylphosphine)palladium(0). The reaction mixture stirred at 95 for 3 h. Upon completion of the reaction as determined by TLC, the solvent was removed under reduced pressure. the residue was dissolved in dichloromethane and filtered by diatomite. The filtrate was washed twice with water and concentrated under reduced pressure. The crude compound was purified by column chromatography eluting with ethyl acetate: hexane to afford the desired compound 8 as a liquid. Yield: 60%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate;palladium diacetate; triphenylphosphine; In 1,4-dioxane; at 85℃; for 4h;Inert atmosphere; | Example A3. General experimental for the Suzuki coupling of aryl bromides or chlorides with boronic acidsGeneral Scheme:K2C03, Pd(OAc)2 Ph3P, dioxaneRepresentative SchePh3P, dioxaneA solution of the aryl bromide or aryl chloride (e.g., 6-bromonicotinonitrile, 1 equiv), 4,4,5,5-tetramethyl -2-vinyl-l,3,2- dioxaborolane (2 equiv), K2C03 (2 equiv), Pd(AcO)2 (0.4 equiv) and PI13P (0.8 equiv) in 1,4-dioxane was stirred under N2 at 85 °C until the reaction was complete (approximately 4 h). After cooling to room temperature, the mixture was quenched with water (50 mL) and extracted with ethyl acetate (3 x 50 mL). The combined organic layers were dried over Na2S04 and concentrated under reduced pressure. The crude vinyl-containing product (e.g., 2-vinylisonicotinonitrile) was purified by silica gel chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
300 mg | With potassium phosphate; 1,1'-bis(di-tertbutylphosphino)ferrocene; palladium diacetate; In tetrahydrofuran; water; at 80℃; for 1.0h;Inert atmosphere; | 1-ethenyl-3-methyl-5-(trifluoromethyl)benzene To <strong>[86845-28-5]1-bromo-3-methyl-5-(trifluoromethyl)benzene</strong> (500 mg, 2.51 mmol) was added THF (5 mL), aqueous tribasic potassium phosphate (2.0 M, 4.18 mL, 8.37 mmol), 2-ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (387 mg, 2.51 mmol), palladium(II) acetate (47 mg, 0.209 mmol), and 1,1'-bis(di-t-butylphosphino)ferrocene (99 mg, 0.209 mmol). The system was flushed with nitrogen gas and was heated at 80 C. for 1 hour. The reaction was filtered and then diluted with ethyl acetate and water. The organic layer was dried over sodium sulfate, filtered and concentrated. The crude product was purified by preparative TLC to yield 1-ethenyl-3-methyl-5-(trifluoromethyl)benzene (300 mg, 1.61 mmol). 1H NMR (500 MHz, CDCl3) delta7.47 (s, 1H), 7.40 (s, 1H), 7.34 (s, 1H), 6.76 (m, 1H), 5.85 (d, J=17.6 Hz, 1H), 2.43 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70.4% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; toluene; at 20 - 90℃;Sealed tube; | Synthesis of 7-vinylquinazoline [0574] To a stirred solution of <strong>[89892-22-8]7-bromoquinazoline</strong> (200 mg, 0.95 mmol) in Toluene: H20 (3 mL,(4:l)) was added 4,4,5,5-tetramethyl-2-vinyl-l,3,2- dioxaborolane (221 mg, 1.43 mmol), Na2CO3(304 mg,2.86 mmol),and Pd(PPh3)4 (55 mg,0.04 mmol) at RT. The reaction mixture was allowed to warm 90 °C stirred for 2h in seal tube. The reaction mixture was filtered, the solvent was evaporated, the crude material was purified by silica gel column chromatography to afford 7- vinylquinazoline (105 mg, 70.4percent) as a thick syrup. 1H-NMR (CDC13, 400 MHz): delta 9.31 (d, 2H), 7.95 (s, 1H), 7.86 (d, 1H), 6.98-6.85 (m, 1H), 6.05 (d, 1H), 5.55 (d, 1H); LC-MS: 98.77percent; 157.0 (M++l); (column; X-Bridge C-18, (50x3.0 mm, 3.5mu); RT 2.51 min. A: 5Mm NH4OAc in water, B: CH3CN, 0.8 ml/min); TLC: 30percent EtOAc/Hexane (Rf: 0.3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With palladium diacetate; caesium carbonate; XPhos; In 2-methyltetrahydrofuran; water; at 60℃; for 1h;Inert atmosphere; | Intermediate 19: 6-ethenvl-2-methvl-3-nitrolvridineA suspension/solution of <strong>[22282-96-8]6-bromo-2-methyl-3-nitropyridine</strong> (500 mg, 2.304 mmol), 2-ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.782 mL, 4.61 mmol), palladium(II) acetate (25.9 mg,0.115 mmol), X-phos (110 mg, 0.230 mmol) and cesium carbonate (3.0 g, 9.22 mmol) in 2-methyltetrahydrofuran (2-MeTHF) (8 mL) and water (2 mL) was stirred under nitrogen at 60 C for1 hour. The reaction mixture was cooled then separated between ethyl acetate and water. Theorganic phase was washed with brine and dried over magnesium sulphate. The solvent was removed in vacuo and the residue was dissolved in DCM (5 mL). This was applied to a silica cartridge and eluted with a gradient of 0100% ethyl acetate in cyclohexane. This gave the crude product (440 mg) as a brown liquid which was used directly in the next step with no furtherpurification. LCMS (2 mm, formic) Rt 0.91 mi m/z (ESj 165 (M+H).1H NMR (400 MHz, CHLOROFORM-o) O ppm 8.28 (d, 1 H), 7.33 (d, 1 H), 6.85 (dd, 1 H), 6.40 (d, 1 H), 5.70 (d, 1 H), 2.89 (5, 3 H). | |
With palladium diacetate; caesium carbonate; XPhos; In 2-methyltetrahydrofuran; water; at 60℃; for 1h;Inert atmosphere; | A suspension/solution of <strong>[22282-96-8]6-bromo-2-methyl-3-nitropyridine</strong> (500 mg, 2.304 mmol), 2-ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.782 mL, 4.61 mmol), palladium(II) acetate (25.9 mg, 0.115 mmol), X-phos (110 mg, 0.230 mmol) and cesium carbonate (3.0 g, 9.22 mmol) in 2-methyltetrahydrofuran (2-MeTHF) (8 mL) and water (2 mL) was stirred under nitrogen at 60 C. for 1 hour. The reaction mixture was cooled then separated between ethyl acetate and water. The organic phase was washed with brine and dried over magnesium sulphate. The solvent was removed in vacuo and the residue was dissolved in DCM (5 mL). This was applied to a silica cartridge and eluted with a gradient of 0-100% ethyl acetate in cyclohexane. This gave the crude product (440 mg) as a brown liquid which was used directly in the next step with no further purification. LCMS (2 min, formic) Rt 0.91 min, m/z (ES+) 165 (M+H). 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 8.28 (d, 1H), 7.33 (d, 1H), 6.85 (dd, 1H), 6.40 (d, 1H), 5.70 (d, 1H), 2.89 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; at 100℃; for 16.5h;Inert atmosphere; Sealed tube; | Step 1[00302j A mixture of <strong>[1749-68-4]6-chloro-2-methylpyrimidin-4-amine</strong> (300 mg, 2.09 mmol), 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (386 mg, 2.51 mmol) and sodiumcarbonate (886 mg, 8.36 mmol) in 1,4-dioxane (9.0 mL) and water (0.9 mL) was bubbled with argon with sonication for 1 mm. The mixture was treated with tetrakis(triphenylphosphine)palladium (169 mg, 0.146 mmol) and the vessel was sealed and subjected to 5 evacuate-fill cycles with argon. The mixture was stirred on a heating block at 100 C for 16.5 h, then was cooled to room temperature, diluted with water andextracted twice with ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate and concentrated under vacuum. The residue was subjected to column chromatography (Isco Combiflash Companion, 24 g silica gel, 20-100% ethyl acetate-hexane, 8 mm, then isocratic) to provide 2-methyl-6-vinylpyrimidin-4-amine as a white solid (189 mg, 67% yield). Mass spectrum m/z 271, (2M+H). ?H NMR (400 MHz,DMSO-d6) oe 6.71 (br. s., 2H), 6.54 (dd, J=17.2, 10.6 Hz, 1H), 6.26 - 6.20 (m, 1H), 6.20 (s, 1H), 5.53 - 5.40 (m, 1H), 2.31 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane;Reflux; Inert atmosphere; | To a mixture of <strong>[320734-35-8]7-bromoindolin-2-one</strong> (10 g, 48 mmol) and sodium carbonate (10 g, 96 mmol) in 1,4-dioxane (100 mL) was added 4,4,5, 5-tetramethyl-2-vinyl-l ,3,2-dioxaborolane (7.3 g, 48 mmol) and Pd(PPh4)3 (2.5 g, 2.4 mmol) at room temperature. The mixture was heated to reflux and stirred under nitrogen overnight. On completion, the mixture was diluted with water (100 mL) and extracted with dichloromethane (3 x 200 mL). The combined organic layers were washed with brine (2 chi 200 mL), dried over anhydrous sodium sulfate, concentrated in vacuo and purified by silica gel column chromatography [petroleum ether: ethyl acetate = 6: 1 ] to give compound B-263 (6.8 g, 90% yield) as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,4-dioxane; water; at 90℃; for 12h;Inert atmosphere; | To a solution of 2, 5-dibromopyrimidine (2.0 g, 8.41 mmol), 4,4,5, 5-tetramethyl-2- vinyl-l,3,2-dioxaborolane (1.56 g, 10.09 mmol), and Pd(dppf)C12 (0.31 g, 0.42 mmol) in dioxane (20 mL) and water (2 mL) was added Na2CC>3 (1.782 g, 16.82 mmol) under N2. The resulting mixture was stirred at 90 C for 12 h. After cooling to RT, the mixture was diluted with water and extracted with EtOAc (100 mL x 3). The combined organic layers were dried over MgS04, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography (2-30% EtOAc in petroleum ether) to give the title compound as a oil. LRMS m/z (M+H) 185.1, 187.1 found, 185.1, 187.1 required. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In water; N,N-dimethyl-formamide; at 60℃;Inert atmosphere; | A mixture of compound 1 (237 mg, 1 mmol), 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (154 mg, 1 mmol), aq. K3PO4 (3 mL, 1 M, 3 mmol) and Pd(dppf)Cl2 (73 mg, 0.1 mmol) in DMF (10 mL) was stirred at 60 C under N2 for 3 h. The reaction mixture was diluted with H2O and extracted with EA. The organic layer was washed with H2O, brine, dried over Na2SO4. After concentrated, the residue was purified by silica gel column chromatography (PE : EA = 30:1) to give the product of compound 2 (170 mg, yield: 92 %). 1H-NMR (CDCl3, 400 MHz) d 8.70 (s, 1H), 8.45 (d, J = 7.2Hz, 1H), 7.41 (d, J = 7.2Hz, 1H), 6.98 (q, J = 6.8Hz, 1H), 5.94 (d, J = 17.6Hz, 1H), 5.60 (d, J = 11.2Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With copper(l) chloride; lithium tert-butoxide; tricyclohexylphosphine; In tetrahydrofuran; at 22℃; for 2h;Inert atmosphere; Glovebox; Sealed tube; | General procedure: In a N2-filled glove box, an oven-dried 1 dram vial equipped with a stir bar was charged with PCy3 (3.1mg, 0.011mmol), LiOt-Bu (12mg, 0.15mmol), and CuCl(1.0mg, 0.010mmol), and thf (1.0mL). The mixture was allowed to stir for 15minat 22C; during this time the solution turned light-yellow. (dan)B-B(pin) (31.2mg, 0.11mmol) was added to the mixture, causing the solution to turn dark brown immediately. Vinyl-B(pin) (15.4mg, 0.10mmol), allylphosphate (29.1mg, 0.15mmol), and thf (0.50mL) were added. The vial was sealed with a cap and electrical tape before removal from the glove box. The resulting mixture was allowed to stir at 22C for 2h. The mixture was then passed through a short plug of celite and neutral alumina (4×1cm) and eluted with Et2O. The organic layer was concentrated under reduced pressure, affording dark brown oil, which was purified by neutralized silica gel chromatography (pre-treated with Et3N, 100% hexanes?hexanes:Et2O=10:1) to afford 1a as light yellow solid (30.4mg, 0.084mmol, 84% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With copper(l) chloride; lithium tert-butoxide; tricyclohexylphosphine; In tetrahydrofuran; at 22℃; for 2h;Inert atmosphere; Glovebox; Sealed tube; | General procedure: In a N2-filled glove box, an oven-dried 1 dram vial equipped with a stir bar was charged with PCy3 (3.1mg, 0.011mmol), LiOt-Bu (12mg, 0.15mmol), and CuCl(1.0mg, 0.010mmol), and thf (1.0mL). The mixture was allowed to stir for 15minat 22C; during this time the solution turned light-yellow. (dan)B-B(pin) (31.2mg, 0.11mmol) was added to the mixture, causing the solution to turn dark brown immediately. Vinyl-B(pin) (15.4mg, 0.10mmol), allylphosphate (29.1mg, 0.15mmol), and thf (0.50mL) were added. The vial was sealed with a cap and electrical tape before removal from the glove box. The resulting mixture was allowed to stir at 22C for 2h. The mixture was then passed through a short plug of celite and neutral alumina (4×1cm) and eluted with Et2O. The organic layer was concentrated under reduced pressure, affording dark brown oil, which was purified by neutralized silica gel chromatography (pre-treated with Et3N, 100% hexanes?hexanes:Et2O=10:1) to afford 1a as light yellow solid (30.4mg, 0.084mmol, 84% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With copper(l) chloride; lithium tert-butoxide; tricyclohexylphosphine; In tetrahydrofuran; at 22℃; for 2h;Inert atmosphere; Glovebox; Sealed tube; | General procedure: In a N2-filled glove box, an oven-dried 1 dram vial equipped with a stir bar was charged with PCy3 (3.1mg, 0.011mmol), LiOt-Bu (12mg, 0.15mmol), and CuCl(1.0mg, 0.010mmol), and thf (1.0mL). The mixture was allowed to stir for 15minat 22C; during this time the solution turned light-yellow. (dan)B-B(pin) (31.2mg, 0.11mmol) was added to the mixture, causing the solution to turn dark brown immediately. Vinyl-B(pin) (15.4mg, 0.10mmol), allylphosphate (29.1mg, 0.15mmol), and thf (0.50mL) were added. The vial was sealed with a cap and electrical tape before removal from the glove box. The resulting mixture was allowed to stir at 22C for 2h. The mixture was then passed through a short plug of celite and neutral alumina (4×1cm) and eluted with Et2O. The organic layer was concentrated under reduced pressure, affording dark brown oil, which was purified by neutralized silica gel chromatography (pre-treated with Et3N, 100% hexanes?hexanes:Et2O=10:1) to afford 1a as light yellow solid (30.4mg, 0.084mmol, 84% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With copper(l) chloride; lithium tert-butoxide; tricyclohexylphosphine; In tetrahydrofuran; at 22℃; for 2h;Inert atmosphere; Glovebox; Sealed tube; | General procedure: In a N2-filled glove box, an oven-dried 1 dram vial equipped with a stir bar was charged with PCy3 (3.1mg, 0.011mmol), LiOt-Bu (12mg, 0.15mmol), and CuCl(1.0mg, 0.010mmol), and thf (1.0mL). The mixture was allowed to stir for 15minat 22C; during this time the solution turned light-yellow. (dan)B-B(pin) (31.2mg, 0.11mmol) was added to the mixture, causing the solution to turn dark brown immediately. Vinyl-B(pin) (15.4mg, 0.10mmol), allylphosphate (29.1mg, 0.15mmol), and thf (0.50mL) were added. The vial was sealed with a cap and electrical tape before removal from the glove box. The resulting mixture was allowed to stir at 22C for 2h. The mixture was then passed through a short plug of celite and neutral alumina (4×1cm) and eluted with Et2O. The organic layer was concentrated under reduced pressure, affording dark brown oil, which was purified by neutralized silica gel chromatography (pre-treated with Et3N, 100% hexanes?hexanes:Et2O=10:1) to afford 1a as light yellow solid (30.4mg, 0.084mmol, 84% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With copper(l) chloride; lithium tert-butoxide; tricyclohexylphosphine; In tetrahydrofuran; at 22℃; for 2h;Inert atmosphere; Glovebox; Sealed tube; | General procedure: In a N2-filled glove box, an oven-dried 1 dram vial equipped with a stir bar was charged with PCy3 (3.1mg, 0.011mmol), LiOt-Bu (12mg, 0.15mmol), and CuCl(1.0mg, 0.010mmol), and thf (1.0mL). The mixture was allowed to stir for 15minat 22C; during this time the solution turned light-yellow. (dan)B-B(pin) (31.2mg, 0.11mmol) was added to the mixture, causing the solution to turn dark brown immediately. Vinyl-B(pin) (15.4mg, 0.10mmol), allylphosphate (29.1mg, 0.15mmol), and thf (0.50mL) were added. The vial was sealed with a cap and electrical tape before removal from the glove box. The resulting mixture was allowed to stir at 22C for 2h. The mixture was then passed through a short plug of celite and neutral alumina (4×1cm) and eluted with Et2O. The organic layer was concentrated under reduced pressure, affording dark brown oil, which was purified by neutralized silica gel chromatography (pre-treated with Et3N, 100% hexanes?hexanes:Et2O=10:1) to afford 1a as light yellow solid (30.4mg, 0.084mmol, 84% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With copper(l) chloride; lithium tert-butoxide; tricyclohexylphosphine; In tetrahydrofuran; at 22℃; for 2h;Inert atmosphere; Glovebox; Sealed tube; | General procedure: In a N2-filled glove box, an oven-dried 1 dram vial equipped with a stir bar was charged with PCy3 (3.1mg, 0.011mmol), LiOt-Bu (12mg, 0.15mmol), and CuCl(1.0mg, 0.010mmol), and thf (1.0mL). The mixture was allowed to stir for 15minat 22C; during this time the solution turned light-yellow. (dan)B-B(pin) (31.2mg, 0.11mmol) was added to the mixture, causing the solution to turn dark brown immediately. Vinyl-B(pin) (15.4mg, 0.10mmol), allylphosphate (29.1mg, 0.15mmol), and thf (0.50mL) were added. The vial was sealed with a cap and electrical tape before removal from the glove box. The resulting mixture was allowed to stir at 22C for 2h. The mixture was then passed through a short plug of celite and neutral alumina (4×1cm) and eluted with Et2O. The organic layer was concentrated under reduced pressure, affording dark brown oil, which was purified by neutralized silica gel chromatography (pre-treated with Et3N, 100% hexanes?hexanes:Et2O=10:1) to afford 1a as light yellow solid (30.4mg, 0.084mmol, 84% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With copper(l) chloride; lithium tert-butoxide; tricyclohexylphosphine; In tetrahydrofuran; at 22℃; for 2h;Inert atmosphere; Glovebox; Sealed tube; | General procedure: In a N2-filled glove box, an oven-dried 1 dram vial equipped with a stir bar was charged with PCy3 (3.1mg, 0.011mmol), LiOt-Bu (12mg, 0.15mmol), and CuCl(1.0mg, 0.010mmol), and thf (1.0mL). The mixture was allowed to stir for 15minat 22C; during this time the solution turned light-yellow. (dan)B-B(pin) (31.2mg, 0.11mmol) was added to the mixture, causing the solution to turn dark brown immediately. Vinyl-B(pin) (15.4mg, 0.10mmol), allylphosphate (29.1mg, 0.15mmol), and thf (0.50mL) were added. The vial was sealed with a cap and electrical tape before removal from the glove box. The resulting mixture was allowed to stir at 22C for 2h. The mixture was then passed through a short plug of celite and neutral alumina (4×1cm) and eluted with Et2O. The organic layer was concentrated under reduced pressure, affording dark brown oil, which was purified by neutralized silica gel chromatography (pre-treated with Et3N, 100% hexanes?hexanes:Et2O=10:1) to afford 1a as light yellow solid (30.4mg, 0.084mmol, 84% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27% | With copper(l) chloride; lithium tert-butoxide; tricyclohexylphosphine; In tetrahydrofuran; at 22℃; for 2h;Inert atmosphere; Glovebox; Sealed tube; | General procedure: In a N2-filled glove box, an oven-dried 1 dram vial equipped with a stir bar was charged with PCy3 (3.1mg, 0.011mmol), LiOt-Bu (12mg, 0.15mmol), and CuCl(1.0mg, 0.010mmol), and thf (1.0mL). The mixture was allowed to stir for 15minat 22C; during this time the solution turned light-yellow. (dan)B-B(pin) (31.2mg, 0.11mmol) was added to the mixture, causing the solution to turn dark brown immediately. Vinyl-B(pin) (15.4mg, 0.10mmol), allylphosphate (29.1mg, 0.15mmol), and thf (0.50mL) were added. The vial was sealed with a cap and electrical tape before removal from the glove box. The resulting mixture was allowed to stir at 22C for 2h. The mixture was then passed through a short plug of celite and neutral alumina (4×1cm) and eluted with Et2O. The organic layer was concentrated under reduced pressure, affording dark brown oil, which was purified by neutralized silica gel chromatography (pre-treated with Et3N, 100% hexanes?hexanes:Et2O=10:1) to afford 1a as light yellow solid (30.4mg, 0.084mmol, 84% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 80℃; for 8h;Inert atmosphere; | To a stirred solution of 2, 5-dibromo-3-3uoropyridine (HM; 2.0 g, 7.87 imnol) in 1.4-dioxane: H2O (4:1, 50 niL) under argon atmosphere were added 4, 4. 5, 5-teirametliyl-2-vinyl- 1 , 3, 2- dioxaborolane (1.2 g, 7.87 mrnol), sodium carbonate (2.5 g? 23.62 rnmol) and purged under argon for 20 mm at RT. Then Pd (PPt-3)4 (227 mg, 0.19 mmoS) was added and the reaction mixture was purged imder argon for 10 mill at RT. The reaction mixture was stirred at 80 C for 8 The progress of fee reaction was monitored by TLC. The reaction mixture was diluted with water (20 mL) and extracted with EtOAc (2 x 20 mL). The combined organic extracts were dried over anhydrous N^SC^ nd concentrated under reduced pressure. The crude material was purified fay silica gel column chromatography (eluent: 2% EtOAc Hexane) to afford compound HN (1.0 g, 4.97 mmol, 63%) as colorless syrup. lB NMR (400 MHz, CDCI3): delta 8.45 (s, Eta), 7.56 (d<L J= 9.4, .2.0 Hz, IH), 6.98-6.90 (m, I H). 6.43 (dd. J= 17.4, 1.6 Hz, IH), 5.62 (dd> J= 10.9, 1.6 Hz, IH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium phosphate; chloro(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl-1,1?-biphenyl)[2-(2?-amino-1,1?-biphenyl?)]palladium(II); In 1,4-dioxane; water; at 80℃; for 0.5h;Inert atmosphere; | Step 4: 6-vinyl-l ,2, 4-triazin-3-amine To a solution of 6-bromo-l ,2,4-triazin-3-amine (1.0 g, 5.7 mmol) in water (3 mL) and 1,4-dioxane (17 mL) were added potassium phosphate (2.4 g, 11 mmol), 4,4,5,5-tetramethyl- 2-vinyl-l ,3,2-dioxaborolane {Aldrich, cat633348: 0.97 g, 6.3 mmol) and chloro(2- dicy clohexylphosphino-2',4',6'-triisopropyl-l , 1 '-biphenyl)[2-(2'-amino- 1 ,1 '- biphenyl)]palladium(II) (0.09 g, 0.1 mmol). The resulting mixture was purged with nitrogen then stirred at 80 C for 30 mins. The reaction mixture was cooled to room temperature, diluted with ethyl acetate then washed with water and brine. Then organic layer was dried over MgS04, filtered, then concentrated to dryness to afford the desired product (580 mg, 83%) as a brownish solid which was used for next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With potassium phosphate; tricyclohexylphosphine tetrafluoroborate; palladium diacetate; In 1,4-dioxane; water; at 110℃; for 12h;Inert atmosphere; | To a 500-mL 3-necked round-bottom flask,was placed a solution of <strong>[103273-01-4]2-bromo-4-tert-butylaniline</strong> (1.38 g,6.05 mmol) in dioxane/water(120 mL) then Pd(OAc)2 (135 mg,0.60 mmol),2-ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.41g,9.15 mmol),PCy3.HBF4 (440 mg,1.19 mmol),and K3P04 (3.81 g,17.97 mmol) were added under nitrogen. The reaction was stirred for 12 h at 110C,quenched by the addition of water,and extracted with EtOAc. The organic extracts were combined and concentrated underreduced pressure. The residue was purified by column chromatography eluting withEtOAc/petroleum ether (1:80) affording 436mg (41%) of the title compound as a colorless oil.Mass Spectrum (LCMS,ESI pos): Calcd. for C12H18N: 176.1 (M+H); Found: 176.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 100℃; | General procedure: To a solution of and halide in the indicated solvent is added boronic acid or ester, carbonate base, and palladium catalyst at room temperature. After stirring at 100 C overnight, the mixture is cooled and concentrated.Following Procedure B using 2 (1 g, 4.81 mmol), dioxane (9 mL), water (1 mL), vinylboronic acid pinacol ester (888 mg, 5.77 mmol), sodium carbonate (1.27 g, 12.02 mmol), and Pd(PI3)4, then purify with silica gel column chromatography to give 3 as an oil (680 mg, 91% yield). (MS: M+Hf 156.1) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84.02% | With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In N,N-dimethyl-formamide;Inert atmosphere; | A solution of Example 65D (600mg, 3.48mmol), vinyl pinacol borate (803.2mg, 5.22mmol), potassium carbonate(961.07mg, 6.95mmol) and Pd(PPh3)4 (602.66mg, 521.53mmol) in DMF (8mL) was stirred at 100°C for 5 hours undernitrogen atmosphere. The solution was cooled, filtered and concentrated in vacuo. The residue was purified by columnchromatography to give the title compound (500mg, yield 84.02percent). 1H NMR (400MHz, CHLOROFORM-d) ppm 8.18 (d,J=8.8 Hz, 1H), 7.72 (d, J=8.8 Hz, 1H), 7.16 (dd, J=11.0, 17.8 Hz, 1H), 6.44 (d, J=17.8 Hz, 1H), 5.85 (d, J=10.8 Hz, 1H),4.10 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a solution of 2.01 g (8.63 mmol) of methyl2-bromo-6-fluorobenzoate in 20 ml of 1,4-dioxane and 4.0 ml of water, 2.80 g (26.4 mmol) of sodium carbonate and 2.90 ml (16.9 mmol) of 4,4,5,5-tetramethyl-2-vinyl-1,3,2- dioxaborolane were added in a nitrogen atmosphere and then stirred at room temperature for 10 minutes while argon gas was bubbled into the reaction solution. Subsequently, 1.02 g (0.883 mmol) of tetrakis(triphenylphosphine)palladium(0) was added thereto at room temperature and reacted at 90 C. for 4 hours with stirring. After completion of the reaction, the reaction solution was diluted with water, followed by extraction twice with ethyl acetate. The whole organic layer thus obtained was dried over anhydrous magnesium sulfate, then filtered, and concentrated under reduced pressure. The obtained concentration residue was subjected to preparative colunm chromatography (apparatus 1, silica gel, n-hexane:ethyl acetate=99: 1-8:2-97:3), and a fraction containing methyl 2-fluoro-6-vinylbenzoate was concentrated under reduced pressure and dried under reduced pressure. To a solution of the obtained concentration residue in 16 ml of 1,4-dioxane and 4.0 ml of water, 1.34 g (12.6 mmol) of sodium carbonate and 1.40 ml (8.16 mmol) of 4,4,5,5-tetramethyl-2-vinyl- 1 ,3,2-dioxaborolane were added in a nitrogen atmosphere and then stirred at room temperature for 10 minutes while argon gas was bubbled into the reaction solution. Subsequently, 446 mg (0.386 mmol) of tetrakis(triphenylphosphine)palladium(0) was added thereto at room temperature and reacted at 90 C. for 3 hours with stirring. Subsequently, 1.10 ml (6.41 mmol) of 4,4,5,5- tetramethyl-2-vinyl- 1 ,3,2-dioxaborolane and 133 mg (0.115 mmol) of tetrakis(triphenylphosphine)palladium(0) were added to the reaction solution and reacted at 90 C. for 3 hours with stirring. After completion of the reaction, the reaction solution was diluted with water, followed by extraction twice with ethyl acetate. The whole organic layer thus obtained was dried over anhydrous magnesium sulfate, then filtered, and concentrated under reduced pressure. The obtained concentration residue was subjected to preparative column chromatography (apparatus 1, silica gel, n-hexane:ethyl acetate=99: 1 -98:2-97:3), and a fraction containing methyl 2-fluoro-6-vinylbenzoate was concentrated under reduced pressure and dried under reduced pressure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; at 90℃; for 16h;Inert atmosphere; | A mixture of 6-iodoisoindolin-l-one (1.00 g, 3.86 mmol, 1.0 equiv.), 4,4,5,5- tetramethyl-2-vinyl-l,3,2-dioxaborolane (0.892 g, 5.79 mmol, 1.5 equiv.),tetrakis(triphenylphosphine)palladium(0) (0.446 g, 0.386 mmol, 0.1 equiv.) and potassium carbonate (1.07 g, 7.72 mmol, 2.0 equiv.) in dioxane (15 mL) and water (3 mL) was degassed and purged with nitrogen 3 times and then stirred at 90C for 16 hours under a nitrogen atmosphere. The reaction mixture was concentrated under reduced pressure to give a residue which was washed petroleum ether/ethyl acetate (10/1, 30 mL) and the solid collected by filtration to give the desired product as a yellow solid (0.6 g, 73%); MS (ESI+) m/z 160.3 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | With [1,1?-bis(di-cyclohexylphosphino)ferrocene]dichloropalladium (II); sodium carbonate; In 1,4-dioxane; water; at 97℃;Inert atmosphere; | A mixture of <strong>[143591-61-1]3-bromo-8-chloroimidazo[1,2-a]pyrazine</strong> (Alchem Pharmtech, catZ-01430: 1.5 g, 6.4 mmol), 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (Aldrich, cat633348: 7.1 mmol), sodium carbonate (1.4 g, 13 mmol) and dichloro[1,1?-bis(dicyclohexylphosphino)ferrocene]palladium( II) (75 mg, 0.099 mmol) in 1,4-dioxane (15 mL) and water (5 mL) was degassed and heated at 97 C. overnight. Ethyl acetate and water were added and the mixture was filtered. The layers were separated and the aqueous phase was further extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by silica gel chromatography eluting with 0-50% ethyl acetate in hexanes to give 0.23 g pale orange solid (20% yield). LC-MS calculated for C8H7ClN3 (M+H)+: m/z=180.0; found 180.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 90℃; for 2h;Inert atmosphere; | 8-Bromo-6-chloro-2-methylimidazo[l,2-b]pyridazine (500 mg, 2.05 mmol, prepared according to example 43) was combined with vinylboronic acid pinacol ester (0.43 mL, 2.3 mmol), Pd(dppf)Cl2 (150 mg, 0.21 mmol) and K2C03 (850 mg, 6.15 mmol) in 1,4-dioxane (10 mL) and H20 (2 mL). The mixture was stirred at 90 C for 2 h under N2. The mixture was partitioned between EtOAc and H20. The organic layer was washed with brine, dried over Na2S04, filtered and concentrated. The residue was chromatographed on silica gel, eluting with 10-20% EtOAc in petroleum ether to yield 6-chloro-2-methyl-8-(prop- l-en-2-yl)imidazo[l,2- b]pyridazine (300 mg, 77%). MS m/z 208.0, 210.0 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68.72% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 90℃; for 16h;Inert atmosphere; | To a stirred mixture of <strong>[262444-15-5](4-bromo-1,3-thiazol-5-yl)methanol</strong>(1 g, 5.15 mmol, 1 equiv.) and 2- ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(1.2 g, 7.73 mmol, 1.5 equiv.) in 1,4-dioxane(30 mL) were added K2CO3(1.4 g, 10.31 mmol, 2 equiv.), H2O(6 mL) and Pd(PPh3)4(297.7 mg, 0.26 mmol, 0.05 equiv.) at room temperature under nitrogen atmosphere. The resulting mixture was stirred for 16 h at 90 degrees celsius under nitrogen atmosphere. The reaction was monitored by LCMS. The resulting mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with PE/EtOAc (30:1 to 5:1) to afford (4- ethenyl-1,3-thiazol-5-yl)methanol (500mg,68.72%) as a yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65.8% | With bis(tri-t-butylphosphine)palladium(0); triethylamine; In toluene; at 80℃; for 16h;Inert atmosphere; | Embodiment 48 (S,E)-2-(2,6-Dimethoxy-4-(2-(4'-methoxy-2-methylbiphenyl-3-yl)vinyl)benz ylamino)-3 -hydroxypropionic acid 48 Synthetic route Synthesis of compound 48-c 2-Bromo-6-chlorotoluene (8.0g, 38.93mmol) and vinylboronic acid pinacol ester (7.3g, 46.72mmol) were dissolved in toluene (100mL), followed by addition of bis(tri-tert-butylphosphine)palladium (1.4g, 2.73mmol) and triethylamine (35.52g, 311.44mmol). After the reaction system was purged three times with nitrogen, the reaction solution was heated to 80C and stirred for 16 hours. Then the reaction solution was cooled to room temperature, diluted with ethyl acetate (100mL), washed successively with water (100mL x 3) and saturated brine (100mL). The organic phase was dried over anhydrous sodium sulfate. The residue was purified by silica gel column chromatography (petroleum ether) to give compound 48-c (7.19g, yield 65.8%). 1H NMR (400 MHz, CDCl3) delta: 7.66-7.61 (d, J = 23.0Hz, 1H), 7.42-7.41 (d, J = 9.5Hz, 1H), 7.32-7.30 (d, J = 9.5Hz, 1H), 7.13-7.09 (t, 1H), 6.06-6.02 (d, J = 22.5Hz, 1H), 2.45 (s, 3H), 1.32 (s, 12H) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With bis(tri-t-butylphosphine)palladium(0); triethylamine; In toluene; at 80℃; for 16h;Inert atmosphere; | 2,6-Dimethoxy-4-bromobenzaldehyde (570mg, 2.34mmol) and vinylboronic acid pinacol ester (504mg, 3.27mmol) were dissolved in toluene (10mL), followed by addition of bis(tri-tert-butylphosphine)palladium (200mg, 0.4mmol) and triethylamine (1.9g, 18.72mmol). After the reaction system was purged three times with nitrogen, the reaction solution was heated to 80C and stirred for 16 hours. Then the reaction solution was cooled to room temperature and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 3:1) to give compound 64-b as a pale brown solid (540mg, yield 73%). 1H-NMR (500MHz, DMSO-d6) delta: 10.32 (s, 1H), 7.31 (d, J=18Hz, 1H), 6.96 (s, 2H), 6.42 (d, J=18Hz, 1H), 3.86 (s, 6H), 1.26 (s, 12H) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In tetrahydrofuran; water; at 100℃; for 1h;Inert atmosphere; Microwave irradiation; | A mixture of 1 -(2-bromo-5-chlorophenyl)ethanone (10 g, 42.8 mmol), 4,4,5,5-tetramethyl-2- vinyl-1 ,3,2-dioxaborolane (9.89 g, 64.2 mmol), Pd(dppf)CI2 (3.13 g, 4.28 mmol) and potassium carbonate (1 1 .84 g, 86 mmol) in THF (40 mL) and H20 (20 mL) was stirred at 100 °C under N2 in a microwave apparatus for 1 h. Water was added and the mixture was extracted with ethyl acetate (3x50 mL). The combined organic layers were washed with saturated NaHCC , water and brine, then dried over MgS04 and filtered. The resulting residue was purified by silica gel flash chromatography (petroleum ether/EtOAc = 10/1 ) to give 1 -(5- chloro-2-vinylphenyl)ethanone (8 g, 39.9 mmol, 93 percent yield) as a yellow solid, m/z: [M + H]+ Calcd for CioHioCIO 181 .0; Found 181 . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 100℃; | Into a 100-mL round-bottom flask, was placed <strong>[145691-59-4](3,5-dibromophenyl)methanol</strong> (2 g, 7.52 mmol, 1.00 eq.), dioxane (40 mL), water(4 mL), 2-ethenyl-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (1.2 g, 7.79 mmol, 1.00 eq.), Pd(PPh3)4 (900 mg, 0.78 mmol, 0.10 eq.), potassium carbonate (3.1 g, 22.43 mmol, 3.00 eq.). The resulting solution was stirred for 1 overnight at 100 C. The solids were filtered out. The resulting mixture was concentrated under vacuum. The resulting solution was diluted with 100 mL of H2O. The resulting solution was extracted with 3x100 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane. This resulted in 1.1 g (69%) of (3-bromo-5- ethenylphenyl)methanol as yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 100℃;Inert atmosphere; | Into a 250-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed <strong>[160233-76-1]6-bromoquinoline-4-carboxylic acid</strong> (2 g, 7.93 mmol, 1.00 equiv), 2-ethenyl-4, 4,5,5- tetramethyl-l,3,2-dioxaborolane (1.8 g, 11.69 mmol, 1.50 equiv), Pd(dppf)Q2CH2Cl2 (1.3 g, 0.20 equiv), potassium carbonate (3.3 g, 23.88 mmol, 3.00 equiv), water (6 mL), dioxane (60 mL). The resulting solution was stirred overnight at lOOoC. The mixture was cooled to 20C. The resulting solution was diluted with 0 (60 mL). The resulting mixture was washed with DCM (100 mL x 2). The pH value of the solution was adjusted to 3-4 with hydrochloric acid (1 mol/L). The resulting solution was extracted with dichloromethane (100 mL x 5) and the organic layers combined and concentrated under vacuum. This resulted in 880 mg (56%) of 6-vinylquinoline-4-carboxylic acid as a brown solid. MS (ES, m/z) [M+H]+: 200. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 100℃;Inert atmosphere; | Compound 40a. To a solution of <strong>[13959-02-9]3-bromoisonicotinic acid</strong> (0.300 g, 1.49 mmol, 1.0 equiv) in Dioxane:water (1:1) (12 mL) was added compound 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (0.34 g, 2.21 mmol, 2.0 equiv), K2CO3 (0.31 g, 2.23 mmol, 1.5 equiv) and resulting reaction mixture purged with N2 gas for 10 minute, followed by the addition of Pd(PPh3)4 (0.086 g, 0.074 mmol. 0.05 equiv). The resulting reaction mixture was heated at 100 C. for overnight. Product formation was confirmed by LCMS. The reaction mixture was concentrated and diluted with water (15 mL) and washed with ethyl acetate (10 mL×2). Aqueous layer was separated and freeze dried to obtain 3-vinylisonicotinic acid (Quant. Yield) as a white solid. LCMS 150.2 [M+H]+1H NMR (400 MHz, DMSO-d6) delta 8.65 (s, 1H), 8.29 (d, J=4.82 Hz, 1H), 7.26-7.39 (m, 1H), 7.23 (d, J=4.38 Hz, 1H), 5.74 (d, J=17.98 Hz, 1H), 5.19 (d, J=10.96 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; water; at 100℃; for 12h;Inert atmosphere; | To a solution of <strong>[74586-53-1]3-bromo-5-methyl-aniline</strong> (2.0 g, 10.75 mmol) in dioxane (20 ml) and H20 (2 ml) was added 4,4,5,5-tetramethyl-2-vinyl-l,3,2- dioxaborolane (4.92 ml, 29.0 mmol), Pd(dppf)Cl2 (1.18 g, 1.61 mmol) and Cs2C03 (10.5 g, 32.3 mmol). The mixture was stirred at 100 C for 12 h under N2. The solution was filtered and the filtrate was concentrated in vacuo. The residue was purified by FCC (25 % EtOAc in petroleum ether) to the title compound as a yellow oil. lH NMR (400 MHz, DMSO-cfc) d ppm 6.57 - 6.49 (m, 1H), 6.45 (s, 1H), 6.43 (s, 1H), 6.32 (s, 1H), 5.62 (d, /= 16 Hz, 1H), 5.12 (d, J= 11 Hz, 1H), 4.97 (s, 2H), 2.15 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a solution of <strong>[886762-75-0]4-bromo-3-fluoro-2-nitroaniline</strong> (100 g, 426 mmol) in DMF (1000 mL) was added NaH (25.5 g, 638 mmol) at 0C. The reaction mixture was stirred for 30 minutes, then di-tert-butyl dicarbonate (196 mL, 851 mmol) was added at 0C. The reaction mixture was stirred at room temperature for 12 h, then poured into ice-cold water (2 L) and extracted with EtOAc (2 x 1L). The organic layer was separated, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude residue was purified by column chromatography, eluting with EtOAc/hexanes (5-10% gradient). The resulting solid was taken up in 1,4-dioxane (300 mL) and water (90 mL), then 4,4,5,5-tetramethyl- 2-vinyl-1,3,2-dioxaborolane (12.7 g, 82.7 mmol) and Na2CO3 (21.9 g, 207 mmol) were added at 0C. The reaction mixture was purged with nitrogen for 30 minutes. Pd(PPh3)4 (7.97 g, 6.89 mmol) was added, and the reaction mixture was again purged with N2 for 30 minutes. The reaction mixture was heated at 100C for 16 h, then diluted with water (400 mL) and extracted with EtOAc (3 x 400 mL). The organic layer was separated, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude residue was purified by column chromatography (silica, 100-200 mesh, 8% EtOAc in hexanes) and taken up in DCM (1.2 L), then purged with ozone gas at -78C for 4 h. The reaction mixture was warmed to r.t., and TPP (33.5 g, 128 mmol) was added. The reaction mixture was stirred at r.t. for 16 h, then concentrated in vacuo. The crude material was purified by column chromatography, eluting with EtOAc/hexanes (20-30% gradient), to furnish the title compound (15.0 g, 12% overall) as a light yellow solid. dH (400 MHz, DMSO-d6) 10.28 (s, 1H), 10.09 (s, 1H), 7.96-8.00 (m, 1H), 7.46 (d, J 8.80 Hz, 1H), 1.44 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70.5% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; at 100℃; for 1h;Inert atmosphere; | Add 3-bromoimidazo [1,2-b] pyridazine (9.9g, 0.05mol), Pd (pph3) 4 (2.89g, 2.5mmol), vinylboronic acid pinacol ester (8.47g, 0.055mol) And Na2CO3 solution (2M) (23mL, 0.05mol) were added to 1,4-dioxane (150mL). Under nitrogen protection, the temperature was raised to 100 C for 1h, and the reaction solution was poured into 200mL saturated NH4Cl aqueous solution, acetic acid. The organic phase was extracted with ethyl acetate (100 mL × 3), the organic phase was separated, dried over anhydrous sodium sulfate, filtered, and concentrated. The product was isolated by column chromatography on silica gel to obtain 5.1 g of the product, with a yield of 70.5%. |
70.5% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; at 100℃; for 1h; | 3-bromoimidazo [1,2-b] pyridazine (9.9 g, 0.05 mol), tetrakis (triphenylphosphonium) palladium (2.89 g, 2.5 mmol),Vinyl boronic acid pinacol ester (8.47g, 0.055mol) and Na2CO3 solution (2M) (23mL, 0.05mol) were added to 1,4-dioxane (150mL).The temperature was raised to 100 C for 1 hour. After the reaction was completed,Pour the reaction solution into 200 mL of saturated aqueous NH4Cl solution.Extracted with ethyl acetate (100mL × 3), separated the organic phase, dried over anhydrous sodium sulfate, and filtered.After concentration, 5.1 g of the product was isolated by column chromatography on silica gel with a yield of 70.5%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 80℃; for 18h;Sealed tube; Inert atmosphere; | A mixture of <strong>[88497-27-2]6-bromopyridazin-3-amine</strong> (XLII) (500 mg, 2.87 mmol), 4,4,5,5-tetramethyl-2-vinyl-l,3,2-dioxaborolane (XLI) (664 mg, 4.31 mmol) K2CO3 (1.19 g, 8.62 mmol), dioxane (5 mL) and water (1 mL) in a 15 mL sealed tube was evacuated under reduced pressure and and filled with N2. Pd(dppf)2Cl2 DCM (210 mg, 0.287 mmol) was added, and the vessel flushed with N2. The reaction mixture was sealed with a Teflon screw cap and the mixture was heated at 80C for 18 h then filtered through a pad of Celite. The filter cake was washed with EtOAc (50 mL), and concentrated under reduced pressure. Flash chromatography (EtOAc: hexanes, gradient elution) afforded 125 mg (36%) of 6-vinylpyridazin-3 -amine (XLIII). ESIMS found for CeHvNs: mlz 122.2 (M+l). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,2-dimethoxyethane; at 120℃; for 3h;Inert atmosphere; | A mixture of <strong>[67754-03-4]methyl 2,5-dichloronicotinate</strong> (CAS: 67754-03-4; 1.95 g, 9.47 mmol), vinylboronic acid pinacol ester (CAS: 75927-49-0; 1.79 mL, 10.4 mmol), Pd(PPfr)4 (547 mg, 0.47 mmol) and K2CO3 (2M, 9.47 mL, 18.9 mmol) in 1 ,2-dimethixyethane (24.6 mL) was stirred under N2 atmosphere for 3 h at 120 C. The suspension was filtered through Celite and evaporated in vacuo. The residue taken up in water and extracted with DCM. The organic layer was dried (NaS04), filtered and evaporated in vacuo. The residue was purified by flash column chromatography (silica, DCM). The desired fractions were collected and concentrated in vacuo to afford intermediate 64 (1.46 g, 78%) as a brown oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 50℃; for 3.0h;Sealed tube; Inert atmosphere; | Step 1: An oven-dried flask was equipped with a magnetic stir bar and charged with 4-bromo- 3,6-dichloropyridazine (0.227 g, 1.0 mmol), [l,l'-bis(diphenylphosphino)ferrocene] (1181) dichloropalladium(II) (75.0 mg, 0.1 mmol), and 4 4,4,5, 5-tetramethyl-2-vinyl-l, 3,2- dioxaborolane (0.l7lmL, 1.0 mmol). The flask was sealed with a rubber septum, and then evacuated and backfilled with argon (repeated a total of 3 X). Dioxane (6 mL) and 2N aq. K2CO3 (1.5 mL, 3.0 mmol) were added and the reaction was heated to 50 C for 3 h. The reaction was cooled to room temperature, diluted with water (2 mL) and extracted with EtOAc (3 X). The combined organic layers were dried over Na2S04, concentrated under reduced pressure, and purified by column chromatography, eluting with a EtO Ac/hexanes gradient (0-50% EtOAc) to provide 3,6-dichloro-4-vinylpyridazine (0.145 g, 82%). |
Tags: 75927-49-0 synthesis path| 75927-49-0 SDS| 75927-49-0 COA| 75927-49-0 purity| 75927-49-0 application| 75927-49-0 NMR| 75927-49-0 COA| 75927-49-0 structure
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