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CAS No. : | 834-67-3 | MDL No. : | MFCD00194739 |
Formula : | C10H12BrNO3S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JWJRLABLXQZFAR-UHFFFAOYSA-N |
M.W : | 306.18 | Pubchem ID : | 253128 |
Synonyms : |
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.4 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 67.44 |
TPSA : | 54.99 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.18 cm/s |
Log Po/w (iLOGP) : | 2.41 |
Log Po/w (XLOGP3) : | 1.39 |
Log Po/w (WLOGP) : | 2.17 |
Log Po/w (MLOGP) : | 1.05 |
Log Po/w (SILICOS-IT) : | 1.4 |
Consensus Log Po/w : | 1.68 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.76 |
Solubility : | 0.533 mg/ml ; 0.00174 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.15 |
Solubility : | 2.18 mg/ml ; 0.00711 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.35 |
Solubility : | 0.138 mg/ml ; 0.00045 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.43 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
100% | With pyridine In dichloromethane at 20℃; for 1h; | |
94% | In tetrahydrofuran at 20℃; | |
94% | In tetrahydrofuran at 20℃; |
90% | With triethylamine In dichloromethane at 0 - 20℃; for 2.16h; | 47.1 Step 1: 4-((4-bromophenyl)sulfonyl)morpholine To a solution of 4-bromobenzenesulfonyl chloride (0.6 g, 2 mmol) in dichloromethane (10 mL) were added morpholine (0.2 mL, 2 mmol) and triethylamine (0.4 mL, 3 mmol) at 0 °C, then the mixture was stirred for 10 min. The mixture was warmed to rt and stirred for 2 h, then the reaction was stopped. The reaction mixture was extracted with DCM (20 mL*3). The combined organic layers were dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo, and the residue was purified by silica-gel column chromatography (DCM:EtOAc=2:1, V/V) to give a white solid (0.62 g, 90%). MS (ESI, pos.ion) m/z: 306.9 (M+2); |
82% | With pyridine; dmap In dichloromethane for 12h; Inert atmosphere; | |
75% | With pyridine; dmap In dichloromethane at 20℃; Inert atmosphere; Schlenk technique; | |
73% | With pyridine at 0 - 20℃; for 1h; | |
In pyridine; water | 18 Example 18, N-[4-(α-Hydroperoxyisopropyl)benzenesulfonyl]morpholine Example 18 N-[4-(α-Hydroperoxyisopropyl)benzenesulfonyl]morpholine To a solution of 1.67 g (19.14 mmol) of morpholine in 50 ml of dry pyridine was added 3.26 g (12.76 mmol) of 4-bromobenzenesulfonyl chloride in an atmosphere of argon, and the mixture was allowed to react at 0°C for 3 hours. To the solution was added water followed by extraction with ethyl acetate. The organic layer was washed with water and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography for separation and purification. Elution with dichloromethane yielded 3.45 g (11.3 mmol) of N-(4-bromobenzenesulfonyl)morpholine. | |
With pyridine | ||
With triethylamine In dichloromethane at 0 - 20℃; | 28.1 Morpholine (58.2 mg, 0.668 mmol) and triethylamine (116 μl, 0.835 mmolwere placed in a round-bottom flask with a stir bar. Dry dichloromethane (5870 μL) was then added and the solution cooled to O0C. 4-bromobenzenesulfonyl chloride (150 mg, 0.556 mmol) was added and the reaction was allowed to warm to room temperature overnight. It was quenched with water and extracted in ethyl acetate. The organic layers were washed with aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. 1H NMR (600 MHz, d6-DMSO): 5 7.87 (d, 2H), 7.65 (d, 2H), 3.62 (t, 4H), 2.85 (t, 4H). | |
With triethylamine In dichloromethane at 0 - 20℃; | 5.1 EXAMPLE 53 - { [4-(morpholin-4-ylsulfonyl)phenyl]amino } - 1 -phenyl- 1 /i-pyrazole-4- carboxamide Step 1. 4-[(4-bromophenyl)sulfpnyl]morpholineMorpholine (58.2 mg, 0.668 mmol) and triethylamine (116 μl, 0.835 mmol)were placed in a round-bottom flask with a stir bar. Dry dichloromethane (5870 μL) was then added and the solution cooled to 00C. 4-bromobenzenesulfonyl chloride (150 mg, 0.556 mmol) was added and the reaction was allowed to warm to room temperature overnight. It was quenched with water and extracted in ethyl acetate. The organic layers were washed with aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give 4- [(4-bromophenyl)sulfonyl] morpholine as a white solid.LRMS (AFCI) calc'd for (CnHi3BrNO2) [M+H]+: 270, 272, Found: 270, 272. | |
With pyridine In dichloromethane for 4h; | ||
With triethylamine In dichloromethane at 20℃; for 0.5h; | 50.A 4-(4-bromophenylsulfonyl)morpholine To a solution of 4-bromobenzene-1-sulfonyl chloride (2.56 g, 10.0 mmol) and triethylamine (1.82 mL, 13 mmol) in DCM (50 mL) was added morpholine (960 mg, 11.0 mmol) dropwise and the mixture was stirred for 30 minutes at room temperature. Then the mixture was concentrated and extracted with EA, washed with 0.1M HCl water solution (2*100 mL), NaHCO3 solution (2*100 mL) and brine, dried and concentrated to give product as a white solid. | |
With triethylamine In dichloromethane at 20℃; for 0.5h; | 16.1.1 Step 1: Synthesis of Compound 4-((4-bromophenyl)sulfonyl)morpholine 4-bromobenzenesulfonyl chloride (5.0 g, 19.6 mmol), triethylamine (TEA) (2.98 mL) and morpholine (1.88 g, 21.53 mmol) were dissolved in DCM (50 mL) and reacted at RT for 30 min. After the reaction was completed, the reaction mixture was poured into water and extracted with DCM. The combined organic phase was washed with 1N HCl, water, brine, dried and concentrated to give 5.21 g of the desired product, which can be directly used in next step without further purification. |
|
In tetrahydrofuran; 1,4-dioxane | ||
With pyridine In dichloromethane for 4h; Cooling with ice; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 40 percent / B(i-PrO)3; n-BuLi / tetrahydrofuran / 18 h / -78 - 20 °C 2: K2CO3 / Pd(dppf)Cl2 / tetrahydrofuran; H2O / 0.08 h / 120 °C / microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 40 percent / B(i-PrO)3; n-BuLi / tetrahydrofuran / 18 h / -78 - 20 °C 2: K2CO3 / Pd(dppf)Cl2 / tetrahydrofuran; H2O / 0.08 h / 120 °C / microwave irradiation 3: piperidine; AcOH / toluene / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | In toluene at 100℃; for 8h; | IV EXAMPLE IV; SYNTHESIS OF [4- [ (4-BROMOPHENYL)] SULFONYL] MORPHOLINE; (Formula Id) A mixture [OF ETHYL-4-BROMOBENZENESULFONATE (LEQUI.)] and morpholine [(EQUI.)] in toluene [(15VOL.)] was heated to [100°C] for [8H.] The reaction mixture was cooled to room temperature and filtered off the solid precipitate. The solid was washed with toluene and dried under vacuum to give 4- [ (4-bromophenyl) sulfonyl] morpholine in 88% yield. The title compound exhibits the following NMR pattern. [['H] NMR (300 MHz, [CDSOD)] : [8] 3.21-3. 28 (4H, [M),] 3.8-3. 87 (4H, [M),] 7.61 (2H, d), 7.77 (2H, d). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate for 4h; Heating / reflux; | 155 Example 155 [ [5-CHLORO-4'- (4-MORPHOLINYLSULFONYL) [1, 1'-BIPHENYL]-2-YL] OXY]- (2S)-PROPANOIC ACID A mixture of the product from example 151 step (iv) (0.126g), sodium carbonate (0.22g), 4- [ (4-BROMOPHENYL) sulfonyl] morpholine (0.16g) and Pd (DPPF) CL2 (0.03g) in dioxane (10ml) was heated under reflux for 4h. The mixture was evaporated and purified by RVHPLC (MECN/AQMI4CL). YIELD 0. 09G. 1H NMR DMSO-D6 : No. 8. 03 (d, 2H), 7.74 (d, 2H), 7.31-7. 39 (m, 2H), 6. 93 (d, 1H), 4.55 (m, 1H), 3.65 (m, 2H), 2.92 (M, 2H), 1.34 (d, 3H) MS: APCI (-ve) 426 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 80℃; for 3h; | |
75% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 90℃; for 2h; Inert atmosphere; | 1 Synthesis of 4-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenylsulfonyl)morpholine (69): Synthesis of 4-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenylsulfonyl)morpholine (69): A mixture of 4-(4-bromophenylsulfonyl)morpholine (68) 6.0 g, 19.7 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l ,3,2-dioxaborolane) (5.0 g, 19.7 mmol ), Pd(dppf)Cl2 (1.6 g, 1.97 mmol) and AcOK (3.8 g, 39.4 mmol) in 100 mL of dioxane was stirred at 90 °C under nitrogen atmosphere for 2 hours. After cooling to room temperature, the mixture was filtered and the filtrate was concentrated under reduced pressure to give the crude product, which was purified by silica gel chromatography (10% EtOAc/petroleum ether) to give 5.2 g of 4-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenylsulfonyl)morpholine (69) as a yellowish solid (yield: 75%). LCMS: m/z 354.0 [M+H]+, = 1.89 min. |
With 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate In 1,4-dioxane at 90℃; for 7h; Heating; | 10 10. 2- [2-Q4-METHOXVPVRIDIN-2-VL) ETHVL1-6-R4- (MORPHOLIN-4-VL-SULFONYL)- PHENVLL^3H-IMIDAZO-R45-BLPVRIDINE A mixture of 0.405 G OF 4- (4-BROMO-BENZENE-SULFONYL)-MORPHOLINE, 0.42 g OF BIS- (PINACOLATO)-DIBORON, 0. 025 G of 1, 1 -BIS- (DIPHENYLPHOSPHINO)-FERROCENE, 0.033 g of [1,1'-bis (diphenyl- phosphino) ferrocene] palladium-dichloride (complex with CIH2C12), 0.442 g of potassium acetate in 8 ml degassed dioxane are heated to 90°C in a sealed tube under N2 for 7 hours. To the resulting mixture 4 ml of degassed dioxane, 0.399 g of 2- [2- (4-METHOXYPYRIDIN-2-YL) ETHYL]-6-IODO-3H-IMIDAZO [4,5- pyridine (starting material A1), 0.121 g OF TETRAKIS (TRIPHENYLPHOSPHINE)-PALLADIUM (0) and a solution of 0.29 g of potassium carbonate and 0.089 g of lithium chloride in 4 mi of degassed water are added under N2. The tube is sealed again, the mixture is heated to 115° under N2 for 17 hours and, after cooling, addition of water and adjusting the pH to 7, it is extracted three times with ethylacetate. The combined organic phases are dried over sodium sulfate, concentrated and the residue is chromatographed on a silica gel column (dichloromethanelmethanol 30-24: 1). Concentration of the CHROMATOGRAPHICALLY pure fractions and crystallization of the residue from ETHYLACETATE gives 0.073 g of the title compound as a solid of m. p. 210-212°C. The mass spectrum shows the molecular peak MH+ at 480.3 Da. |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 70℃; for 4h; | 50.B 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylsulfonyl)morpholine To a solution of 4-(4-bromophenylsulfonyl)morpholine (3.06 g, 10 mmol) in DMSO (20 mL) was added 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (3.3 g, 13.0 mmol), [1,1'-Bis(diphenylphosphino)ferrocene]palladium(11) chloride (730 mg, 1.0 mmol) and potassium acetate (1.47 g, 15 mmol). Then the mixture was heated to 70° C. for 4 hours. After cooling the mixture was extracted with EA, wash with brine, dried and purified by silica gel chromatography, eluting with PE/EA=1/1 to give product as a yellow solid. MS (m/z): 354 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 60℃; for 40h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate In water; acetonitrile at 85℃; for 18h; Inert atmosphere of nitrogen; | 27.i (S)-tert-Butyl 4-( 1 -amino- 1 -oxo-3-(4-(4,4,5 ,5 -tetramethyl- 1 ,3 ,2-dioxaborolan-2- yl)phenyl)propan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 16, step (i), 250 mg) in acetonitrile (8 niL) with 4-(4-bromophenylsulfonyl)morpholine (148 mg) was treated with aqueous sodium carbonate (2M, 0.5 mL) and nitrogen was bubbled through the mixture. 1,1 δ(Di-tert-butylphosphino)ferrocene palladium dichloride (5 mg) was added and the mixture was heated at 85 0C for 18 h under nitrogen. The reaction mixture was evaporated onto silica and purified by chromatography on silica eluting with ethyl acetate / ohexane (50:50 to 100:0) to afford the sub-titled compound (240 mg).m/e (MultiMode-) 615 [M-H]" |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With 2,2,6,6-tetramethylheptane-3,5-dione; caesium carbonate; copper(I) bromide In 1-methyl-pyrrolidin-2-one at 110℃; Inert atmosphere; | 4.4.1. General procedure for the synthesis of compounds 8 and 12A-E General procedure: Methyl 3-hydroxy-5-((3-methylbut-2-en-1-yl)oxy) benzoate 734 (1.6 g, 6.8 mmol, 1 equiv), aryl bromide 636 or 11A-E (7.5 mmol, 1.1 equiv), copper (I) bromide (0.34 mmol, 0.5 equiv) and cesium carbonate (3.32 g, 10.2 mmol, 1.5 equiv) were added to a pear-shaped Schlenk flask. Degased NMP (9 mL) was added via needle, then TMHD (0.13 mmol, 0.1 equiv) was dropped. The reaction mixture was heated at 110 °C under nitrogen, and then cooled to the room temperature. The reaction mixture was filtered through a pad of celite and washed with EtOAc. Combined filtrates were washed subsequently with 2 N HCl, 2 M NaOH, and 10% NaCl. The resulting organic layer was dried over anhydrous NaSO4 and concentrated. The crude product was then purified by flash column chromatography to give the title intermediate in 70-80% yield (8 and 12A-E). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 2,2,6,6-tetramethylheptane-3,5-dione; caesium carbonate; copper(I) bromide / 1-methyl-pyrrolidin-2-one / 110 °C / Inert atmosphere 2: lithium hydroxide / tetrahydrofuran; water / 2 h / Reflux 3: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.5 h / 60 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 2,2,6,6-tetramethylheptane-3,5-dione; caesium carbonate; copper(I) bromide / 1-methyl-pyrrolidin-2-one / 110 °C / Inert atmosphere 2: lithium hydroxide / tetrahydrofuran; water / 2 h / Reflux 3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 0 °C / Reflux 4: pyridine / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 2,2,6,6-tetramethylheptane-3,5-dione; caesium carbonate; copper(I) bromide / 1-methyl-pyrrolidin-2-one / 110 °C / Inert atmosphere 2: lithium hydroxide / tetrahydrofuran; water / 2 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 2,2,6,6-tetramethylheptane-3,5-dione; caesium carbonate; copper(I) bromide / 1-methyl-pyrrolidin-2-one / 110 °C / Inert atmosphere 2: lithium hydroxide / tetrahydrofuran; water / 2 h / Reflux 3: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.5 h / 60 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 2,2,6,6-tetramethylheptane-3,5-dione; caesium carbonate; copper(I) bromide / 1-methyl-pyrrolidin-2-one / 110 °C / Inert atmosphere 2: lithium hydroxide / tetrahydrofuran; water / 2 h / Reflux 3: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.5 h / 60 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 2,2,6,6-tetramethylheptane-3,5-dione; caesium carbonate; copper(I) bromide / 1-methyl-pyrrolidin-2-one / 110 °C / Inert atmosphere 2: lithium hydroxide / tetrahydrofuran; water / 2 h / Reflux 3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 0 °C / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-butyllithium In tetrahydrofuran at -78℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In ethanol; water; toluene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | Stage #1: sodium 4-bromobenzenesulfinate With iodine at 20℃; for 0.333333h; Green chemistry; Stage #2: morpholine In ethanol at 20℃; for 3h; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium hydrogencarbonate; sodium sulfite; water / 4 h / 80 °C 2.1: iodine / 0.33 h / 20 °C / Green chemistry 2.2: 3 h / 20 °C / Green chemistry | ||
Multi-step reaction with 2 steps 1: hydrazine hydrate / tetrahydrofuran / 0.5 h / 0 - 20 °C 2: iodine; tert.-butylhydroperoxide / 1,2-dichloro-ethane; decane / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With 2-Ethylhexanoic acid; palladium diacetate; potassium carbonate; tricyclohexylphosphine In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 20h; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 3 h / 80 °C 2: palladium diacetate; triethylamine / water; ethanol / 1 h / 120 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 3 h / 80 °C 2: palladium diacetate; triethylamine / water; ethanol / 1 h / 120 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 3 h / 80 °C 2: palladium diacetate; triethylamine / water; ethanol / 1 h / 120 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | Stage #1: 4-(benzoyloxy)morpholine; sodium 4-bromobenzenesulfinate In 1,2-dichloro-ethane at 30℃; for 12h; Schlenk technique; Inert atmosphere; Stage #2: With copper(ll) bromide In 1,2-dichloro-ethane for 12h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With tert.-butylhydroperoxide; iodine In water at 20℃; for 0.0166667h; | General procedure for the synthesis of sulfonamides 8-12 General procedure: To a mixture of arylsulfonyl hydrazide 1 (0.5 mmol) and amine (0.75 mmol) was added TBHP (0.2 mL, 70% wt/wt in H2O, 2.0 mmol) followed by molecular iodine (0.025 g, 0.10 mmol, 20 mol%) at room temperature. The reaction was completed after the addition of iodine within a minute. After completion of the reaction, as indicated by TLC, the reaction mixture was diluted with ethyl acetate, and quenched with saturated sodium thiosulphate solution and extracted twice with ethyl acetate (2 × 10 mL). The organic layer was washed with water and dried over anhyd. sodium sulphate. The solvent was evaporated in vacuo to afford pure sulfonamide derivative (8-12). |
95% | With ammonium bromide In water; acetonitrile at 25 - 30℃; Electrolysis; | General procedure General procedure: An undivided cell was equipped with a carbon platea node (7.5 cm2) and a Fe plate cathode (7.5 cm2) and connected to a DC regulated power supply. The solution of corresponding amine 2 (1.5-4.83 mmol) in 30 ml MeCN-H2O (1:1), arenesulfonohydrazide 1 (300 mg, 1.00-1.61 mmol) and supporting electrolyte KBr, NH4Br (0.5-0.8 mmol;molar ratio to 1 was 1:2) were added to the cell. The mixture was electrolyzed with constant current (35-40 mA cm-2) at 25-30 °C under magnetic stirring. Then the solvent was removed under reduced pressure(10-20 Torr). The residue was diluted with EtOAc (50 ml) and washed with brine (2 × 8 ml) and water (2 × 8 ml), dried over Na2SO4, and concentrated under reduced pressure (10-20 Torr). Then it was purified by recrystallization from ethanol. |
86% | With tert.-butylhydroperoxide; iodine In decane; 1,2-dichloro-ethane at 20℃; for 1h; |
74% | With copper(ll) bromide In acetonitrile at 50℃; for 12h; | General procedure for Cu-catalyzed aerobic oxidative coupling reaction General procedure: To a 50 mL round-bottom flask equipped with a magnetic stir bar, sulfonyl hydrazide (0.5 mmol), CuBr2 (10 mol%, 0.05 mmol) and CH3CN (2.0 mL) was added. After amine (3 equiv, 1.5 mmol) and CH3CN (2.0 mL) were added, reaction mixture was stirred at 50 °C under air. After 12 h, the mixture was diluted by adding EtOAc and quenched with a saturated aqueous solution of NH4Cl. Two layers were separated, and aqueous layer was extracted with EtOAc. The combined organic layer was dried over MgSO4, filtered, and concentrated on rotary evaporator. The residue was purified by column chromatography to give sulfonamide products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52.3% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 90℃; for 5h; Inert atmosphere; | 190.2 Step 2: Preparation of (4-(5-(4-(morpholinosulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)(thiophen-2-yl)methanone (53) Step 2: Preparation of (4-(5-(4-(morpholinosulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)(thiophen-2-yl)methanone (53) (0801) (0802) A suspension solution of the intermediate 51 (500 mg, 1.15 mmol, 1.1 eq), 4-((4-bromophenyl)sulfonyl)morpholine (319 mg, 1.04 mmol, 1.0 eq) and Na2CO3 (220 mg, 2.08 mmol, 2.0 eq) in DME (8 mL) and water (2 mL) was subjected to purging in nitrogen, treated with Pd(PPh3)4 (120 mg, 0.10 mmol, 0.1 eq) and stirred at 90° C. for 5 hours. The reaction mixture thus obtained was cooled to room temperature, concentrated, added with water (5 mL) and EtOAc (20 mL), filtered and washed with MeCN (5 mL), DCM and MeOH (10: 1, 5 mL) to give the compound 53 (322 mg, 0.60 mmol, 52.3%) as a yellow solid. (0803) 1H NMR (400 MHz, DMSO-d6) δ 11.96 (s, 1H), 8.64-8.63 (m, 1H), 8.56 (s, 1H), 8.09-8.07 (m, 2H), 7.82-7.80 (s, 2H), 7.70 (m, 1H), 7.54-7.53 (m, 1H), 7.19-7.17 (m, 1H), 6.38 (s, 1H), 4.42 (s, 2H), 3.90-3.87 (m, 2H), 3.67-3.65 (m, 4H), 2.92 (m, 4H), 2.68 (s, 2H); MS (m/z): 535.1 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Sealed tube; Inert atmosphere 1.2: 20 °C / Sealed tube; Inert atmosphere 2.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / water; ethanol / 2 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Sealed tube; Inert atmosphere 1.2: 20 °C / Sealed tube; Inert atmosphere 2.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / water; ethanol / 2 h / Reflux 3.1: trichlorophosphate / 2 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Sealed tube; Inert atmosphere 1.2: 20 °C / Sealed tube; Inert atmosphere 2.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / water; ethanol / 2 h / Reflux 3.1: trichlorophosphate / 2 h / Reflux 4.1: toluene-4-sulfonic acid / dimethyl sulfoxide / 24 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Sealed tube; Inert atmosphere 1.2: 20 °C / Sealed tube; Inert atmosphere 2.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / water; ethanol / 2 h / Reflux 3.1: trichlorophosphate / 2 h / Reflux 4.1: toluene-4-sulfonic acid / dimethyl sulfoxide / 24 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Sealed tube; Inert atmosphere 1.2: 20 °C / Sealed tube; Inert atmosphere 2.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / water; ethanol / 2 h / Reflux 3.1: trichlorophosphate / 2 h / Reflux 4.1: toluene-4-sulfonic acid / dimethyl sulfoxide / 24 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Sealed tube; Inert atmosphere 1.2: 20 °C / Sealed tube; Inert atmosphere 2.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / water; ethanol / 2 h / Reflux 3.1: trichlorophosphate / 2 h / Reflux 4.1: toluene-4-sulfonic acid / dimethyl sulfoxide / 24 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Sealed tube; Inert atmosphere 1.2: 20 °C / Sealed tube; Inert atmosphere 2.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / water; ethanol / 2 h / Reflux 3.1: trichlorophosphate / 2 h / Reflux 4.1: toluene-4-sulfonic acid / dimethyl sulfoxide / 24 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Sealed tube; Inert atmosphere 1.2: 20 °C / Sealed tube; Inert atmosphere 2.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / water; ethanol / 2 h / Reflux 3.1: trichlorophosphate / 2 h / Reflux 4.1: toluene-4-sulfonic acid / dimethyl sulfoxide / 24 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Sealed tube; Inert atmosphere 1.2: 20 °C / Sealed tube; Inert atmosphere 2.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / water; ethanol / 2 h / Reflux 3.1: trichlorophosphate / 2 h / Reflux 4.1: toluene-4-sulfonic acid / dimethyl sulfoxide / 24 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Sealed tube; Inert atmosphere 1.2: 20 °C / Sealed tube; Inert atmosphere 2.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / water; ethanol / 2 h / Reflux 3.1: trichlorophosphate / 2 h / Reflux 4.1: toluene-4-sulfonic acid / dimethyl sulfoxide / 24 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Sealed tube; Inert atmosphere 1.2: 20 °C / Sealed tube; Inert atmosphere 2.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / water; ethanol / 2 h / Reflux 3.1: trichlorophosphate / 2 h / Reflux 4.1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 24 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Sealed tube; Inert atmosphere 1.2: 20 °C / Sealed tube; Inert atmosphere 2.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / water; ethanol / 2 h / Reflux 3.1: trichlorophosphate / 2 h / Reflux 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; potassium <i>tert</i>-butylate / 1,4-dioxane / 24 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Sealed tube; Inert atmosphere 1.2: 20 °C / Sealed tube; Inert atmosphere 2.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / water; ethanol / 2 h / Reflux 3.1: trichlorophosphate / 2 h / Reflux 4.1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 24 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Sealed tube; Inert atmosphere 1.2: 20 °C / Sealed tube; Inert atmosphere 2.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / water; ethanol / 2 h / Reflux 3.1: trichlorophosphate / 2 h / Reflux 4.1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 24 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Sealed tube; Inert atmosphere 1.2: 20 °C / Sealed tube; Inert atmosphere 2.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / water; ethanol / 2 h / Reflux 3.1: trichlorophosphate / 2 h / Reflux 4.1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 24 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Sealed tube; Inert atmosphere 1.2: 20 °C / Sealed tube; Inert atmosphere 2.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / water; ethanol / 2 h / Reflux 3.1: trichlorophosphate / 2 h / Reflux 4.1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 24 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Sealed tube; Inert atmosphere 1.2: 20 °C / Sealed tube; Inert atmosphere 2.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / water; ethanol / 2 h / Reflux 3.1: trichlorophosphate / 2 h / Reflux 4.1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 24 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Sealed tube; Inert atmosphere 1.2: 20 °C / Sealed tube; Inert atmosphere 2.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / water; ethanol / 2 h / Reflux 3.1: trichlorophosphate / 2 h / Reflux 4.1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 24 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Sealed tube; Inert atmosphere 1.2: 20 °C / Sealed tube; Inert atmosphere 2.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / water; ethanol / 2 h / Reflux 3.1: trichlorophosphate / 2 h / Reflux 4.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C 4.2: 1 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Sealed tube; Inert atmosphere 1.2: 20 °C / Sealed tube; Inert atmosphere 2.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / water; ethanol / 2 h / Reflux 3.1: trichlorophosphate / 2 h / Reflux 4.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C 4.2: 1 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Sealed tube; Inert atmosphere 1.2: 20 °C / Sealed tube; Inert atmosphere 2.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / water; ethanol / 2 h / Reflux 3.1: trichlorophosphate / 2 h / Reflux 4.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C 4.2: 1 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Sealed tube; Inert atmosphere 1.2: 20 °C / Sealed tube; Inert atmosphere 2.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / water; ethanol / 2 h / Reflux 3.1: trichlorophosphate / 2 h / Reflux 4.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C 4.2: 1 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Sealed tube; Inert atmosphere 1.2: 20 °C / Sealed tube; Inert atmosphere 2.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / water; ethanol / 2 h / Reflux 3.1: trichlorophosphate / 2 h / Reflux 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; potassium <i>tert</i>-butylate / 1,4-dioxane / 24 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Sealed tube; Inert atmosphere 1.2: 20 °C / Sealed tube; Inert atmosphere 2.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / water; ethanol / 2 h / Reflux 3.1: trichlorophosphate / 2 h / Reflux 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; potassium <i>tert</i>-butylate / 1,4-dioxane / 24 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Sealed tube; Inert atmosphere 1.2: 20 °C / Sealed tube; Inert atmosphere 2.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / water; ethanol / 2 h / Reflux 3.1: trichlorophosphate / 2 h / Reflux 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; potassium <i>tert</i>-butylate / 1,4-dioxane / 24 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Sealed tube; Inert atmosphere 1.2: 20 °C / Sealed tube; Inert atmosphere 2.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / water; ethanol / 2 h / Reflux 3.1: trichlorophosphate / 2 h / Reflux 4.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C 4.2: 1 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With iodine pentoxide In acetonitrile at 60℃; for 12h; Sealed tube; | |
62% | With iodine pentoxide In acetonitrile at 20 - 60℃; for 12h; | 11 Example 11: P-bromothiophenol (1.89 g, 10 mmol) was added in a 50 mL round bottom flask at room temperature,Morpholine (1.75 ml, 20 mmol), acetonitrile (20 mL) and diiodide pentoxide (10 mmol).Then, the reaction mixture was stirred at 60 ° C for 12 hours (TLC detection reaction).Then, the reaction was stopped and concentrated under reduced pressure to obtain a crude product. Finally with petroleum ether andEthyl acetate in a mixture of eluent, and flash column chromatography (silica gel column)The corresponding product sulfonamide compound (1.88 g of yellow crystals, yield 62%) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With nickel(II) bromide dimethoxyethane; 4,4'-di-tert-butyl-2,2'-bipyridine; lithium bromide In 1,2-dimethoxyethane; N,N-dimethyl acetamide at 20℃; for 4.5h; Inert atmosphere; Electrochemical reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With 1,4-diazabicyclo [2.2.2] octane-1,4-diium-1,4-disulfinate; copper(II) bis(trifluoromethanesulfonate); isopropyl alcohol In 1,2-dichloro-ethane at 80℃; for 0.5h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In water; N,N-dimethyl-formamide at 90℃; for 1h; | 47.2 Step 2: N-(1-((1-cyanocyclopropyl)carbamoyl)-4,4-difluorocyclohexyl)-6-(4-(morpholino sulfonyl)phenyl)benzofuran-2-carboxamide To a 50 mL two-neck round-bottom flask were added N-(1-((1-cyanocyclopropyl)carbamoyl)-4,4-difluorocyclohexyl)-6-(4,4,5,5-tetramethyl-1,3,2-dio xaborolan-2-yl)benzofuran-2-carboxamide (70 mg, 0.13 mmol), DMF (6 mL) and 4-((4-bromophenyl)sulfonyl)morpholine (51 mg, 0.17mmol), then Pd(dppf)Cl2·CH2Cl2 (20 mg, 0.02 mmol) and aqueous potassium carbonate (0.2 mL, 2 mol/L) were added to the mixture. The mixture was stirred at 90 °C for 1 h. After the reaction was completed, the reaction mixture was washed with saturated brine (20 mL). The resulting mixture was extracted with EtOAc (20 mL*3). The combined organic layers were dried over anhydrous Na2SO4, and filtered. The filtrate was concentrated in vacuo, and the residue was purified by silica-gel column chromatography (DCM:EtOAc=1:1, V/V)to give a white solid (52 mg, 65%). MS (ESI, pos.ion) m/z: 613.1 (M+1); 1H NMR (400 MHz, DMSO-d6) δ 8.79 (s, 1H), 8.55 (s, 1H), 8.14-8.04 (m, 3H), 7.94 (d, J = 8.2 Hz, 1H), 7.85 (d, J = 8.5 Hz, 2H), 7.80-7.74 (m, 2H), 3.70-3.63 (m, 4H), 2.96-2.90 (m, 4H), 2.21 (d, J = 5.9 Hz, 2H), 2.07 (d, J = 15.2 Hz, 6H), 1.46 (dd, J = 8.2, 5.4 Hz, 2H), 1.10-1.05 (m, 2H). 19F NMR (376 MHz, DMSO-d6) δ -92.76 (d, J = 236.2 Hz), -98.20 (d, J = 231.0 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With potassium phosphate monohydrate; C50H60F3NO6PPdS In tetrahydrofuran; water at 55℃; for 20h; | |
89% | With C35H47O3P*C15H16N(1-)*CH3O3S(1-)*Pd(2+); triethylamine In water at 45℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; bis(tri-t-butylphosphine)palladium(0) / toluene / 3 h / Inert atmosphere; Heating 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate / water; 1,4-dioxane / 6 h / Heating; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; bis(tri-t-butylphosphine)palladium(0) / toluene / 3 h / Inert atmosphere; Heating 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate / water; 1,4-dioxane / 6 h / Heating; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis(tri-t-butylphosphine)palladium(0); N-ethyl-N,N-diisopropylamine In toluene for 3h; Inert atmosphere; Heating; | General procedure for the synthesis of 8 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 |
---|---|---|
71% | With potassium phosphate monohydrate; C50H60F3NO6PPdS In water at 55℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With potassium phosphate monohydrate; palladium diacetate; N<SUB>2</SUB>Phos In water; toluene at 45℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With potassium phosphate; 5,5'-dimethyl-2,2'-bipyridine; nickel(II) bromide diethylene glycol dimethyl ether; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate In 1,4-dioxane at 20℃; for 20h; Irradiation; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.8 g | With palladium diacetate; triethylamine; triphenylphosphine at 150℃; for 6h; Inert atmosphere; Sealed tube; | 16.1.2 Step 2: Synthesis of Compound ethyl 3-(4-(morpholinosulfonyl)phenyl)acrylate Under the protection of nitrogen atmosphere, 4-((4-bromophenyl)sulfonyl)morpholine (2.0 g, 6.53 mmol), ethyl acrylate (849 mg, 8.49 mmol), Pd(OAc)2 (43.88 mg, 0.2 mmol) and PPh3 (68.89 mg, 0.26 mmol) were added in TEA (3 mL) and stirred at 150° C. for 6 hours in sealed tube. The reaction mixture was cooled, poured into ice-water and extracted with EA. The combined organic phase was dried with Na2SO4 and concentrated. The crude product was separated by column chromatography to give the desired product (1.8 g, yield 85%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With tri(cyclohexylmethyl)acetic acid; potassium carbonate; triphenylphosphine In toluene at 100℃; for 4h; Schlenk technique; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89 % ee | With C23H20N2O2*Ni(2+)*2Br(1-); magnesium chloride; zinc In N,N-dimethyl-formamide at 0℃; Overall yield = 70 percent; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: morpholine With sulfuryl dichloride; triethylamine In acetonitrile at 0 - 30℃; for 0.5h; Inert atmosphere; Stage #2: 4-Bromophenylboronic acid With disodium hydrogenphosphate; bis(benzonitrile)palladium(II) dichloride; tris(2,6-dimethoxyphenyl)phosphine In tetrahydrofuran; acetonitrile at 70℃; for 16h; Inert atmosphere; | 2 Example 2 At room temperature, place the dry test tube reaction tube in high-purity nitrogen or argon to replace the gas, make the system under anhydrous and oxygen-free conditions, add 1.5mL acetonitrile and 0.5mmol sulfonyl chloride and cool to 0, then add dropwise 0.2mmol of morpholine and 0.5mmol of triethylamine were placed in a heating device at 30°C and stirred for 0.5 hours. Take another reaction tube, add 0.01mmol of bisbenzonitrile palladium dichloride, 0.02mmol of tris(2,6-dimethoxybenzene)phosphine, 0.6mmol of disodium hydrogen phosphate and 0.4mmol of 4 -Bromophenylboronic acid, place the reaction tube in high-purity nitrogen or argon to replace the gas, make the system under anhydrous and oxygen-free conditions, add 1.0mL tetrahydrofuran and 0.5mL acetonitrile, and then use a syringe to add the mixed solution obtained in the previous step. The resulting mixture was stirred in a heating device at 70°C for 16 hours. After TLC monitors the complete reaction, the reaction solution is concentrated under reduced pressure, and the mixture of petroleum ether and ethyl acetate is used as the mobile phase for column chromatography to separate the corresponding 4-(4-bromobenzenesulfonyl)). Example 2 of morpholine 4-((4-Bromophenyl)sulfonyl)morpholine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With disodium hydrogenphosphate; bis(benzonitrile)palladium(II) dichloride; tris(2,6-dimethoxyphenyl)phosphine In tetrahydrofuran; acetonitrile at 70℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With nickel(II) bromide diethylene glycol dimethyl ether; 4,4'-Dimethoxy-2,2'-bipyridin; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate In N,N-dimethyl acetamide at 20℃; for 16h; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 4,4'-di-tert-butyl-2,2'-bipyridine nickel(II) bromide; sodium hydrogencarbonate In N,N-dimethyl acetamide at 20℃; for 12h; Irradiation; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 4,4'-di-tert-butyl-2,2'-bipyridine nickel(II) bromide; sodium hydrogencarbonate In N,N-dimethyl acetamide at 20℃; for 12h; Irradiation; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 4,4'-di-tert-butyl-2,2'-bipyridine nickel(II) bromide; sodium hydrogencarbonate In N,N-dimethyl acetamide at 20℃; for 12h; Irradiation; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 4,4'-di-tert-butyl-2,2'-bipyridine nickel(II) bromide; sodium hydrogencarbonate In N,N-dimethyl acetamide at 20℃; for 12h; Irradiation; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 4,4'-di-tert-butyl-2,2'-bipyridine nickel(II) bromide; sodium hydrogencarbonate In N,N-dimethyl acetamide at 20℃; for 12h; Irradiation; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 4,4'-di-tert-butyl-2,2'-bipyridine nickel(II) bromide; sodium hydrogencarbonate In N,N-dimethyl acetamide at 20℃; for 12h; Irradiation; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 4,4'-di-tert-butyl-2,2'-bipyridine nickel(II) bromide; sodium hydrogencarbonate In N,N-dimethyl acetamide at 20℃; for 12h; Irradiation; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11% | With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 4,4'-di-tert-butyl-2,2'-bipyridine nickel(II) bromide; sodium hydrogencarbonate In N,N-dimethyl acetamide at 20℃; for 12h; Irradiation; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 4,4'-di-tert-butyl-2,2'-bipyridine nickel(II) bromide; sodium hydrogencarbonate In N,N-dimethyl acetamide at 20℃; for 12h; Irradiation; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With nickel(II) bromide dimethoxyethane; potassium phosphate; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; tetrabutylammomium bromide; 4,4'-di-tert-butyl-2,2'-bipyridine In acetonitrile; benzene for 24h; Glovebox; Sealed tube; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With nickel(II) bromide dimethoxyethane; potassium phosphate; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; tetrabutylammomium bromide; 4,4'-di-tert-butyl-2,2'-bipyridine In acetonitrile; benzene for 24h; Glovebox; Sealed tube; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72.9 mg | With potassium phosphate; tris(triethylsilyl)silane; (Ir[dF(CF3)ppy]2(dtbpy))PF6; NiBr<SUB>2</SUB>(4,4'-dimethoxy-2,2'-bipyridine) In dichloromethane; acetonitrile at 20℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47.3 mg | With potassium phosphate; tris(triethylsilyl)silane; (Ir[dF(CF3)ppy]2(dtbpy))PF6; NiBr<SUB>2</SUB>(4,4'-dimethoxy-2,2'-bipyridine) In dichloromethane; acetonitrile at 20℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57.4 mg | With potassium phosphate; tris(triethylsilyl)silane; (Ir[dF(CF3)ppy]2(dtbpy))PF6; NiBr<SUB>2</SUB>(4,4'-dimethoxy-2,2'-bipyridine) In dichloromethane; acetonitrile at 20℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69.4 mg | With potassium phosphate; tris(triethylsilyl)silane; (Ir[dF(CF3)ppy]2(dtbpy))PF6; NiBr<SUB>2</SUB>(4,4'-dimethoxy-2,2'-bipyridine) In dichloromethane; acetonitrile at 20℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With tributyl-amine; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; NiBr2.(4,4′-ditert-butyl-2,2′-bipyridyl) In 1,4-dioxane at 32℃; for 40h; Inert atmosphere; Sealed tube; Irradiation; |
Tags: 834-67-3 synthesis path| 834-67-3 SDS| 834-67-3 COA| 834-67-3 purity| 834-67-3 application| 834-67-3 NMR| 834-67-3 COA| 834-67-3 structure
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P272 | Contaminated work clothing should not be allowed out of the workplace. |
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H242 | Heating may cause a fire |
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H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
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H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
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H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
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H351 | Suspected of causing cancer |
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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 |
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H373 | May cause damage to organs through prolonged or repeated exposure |
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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 |
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