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Chemical Structure| 1243312-43-7 Chemical Structure| 1243312-43-7

Structure of 1243312-43-7

Chemical Structure| 1243312-43-7

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Product Details of [ 1243312-43-7 ]

CAS No. :1243312-43-7
Formula : C12H18BNO3
M.W : 235.09
SMILES Code : CC1(C)C(C)(C)OB(C2=C(OC)C=NC=C2)O1
MDL No. :MFCD13182222

Safety of [ 1243312-43-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 1243312-43-7 ]

* 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.

  • Downstream synthetic route of [ 1243312-43-7 ]

[ 1243312-43-7 ] Synthesis Path-Downstream   1~22

  • 2
  • [ 1243312-43-7 ]
  • 4-bromo-1-nitro-2-(propan-2-yloxy)benzene [ No CAS ]
  • [ 1462950-54-4 ]
YieldReaction ConditionsOperation in experiment
2.63 g With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; water; at 130℃; for 0.333333h;Microwave irradiation; Method 3 4-(5-Methoxy-1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-2-(propan-2-yloxy)aniline A mixture of 2.5 g of 4-bromo-1-nitro-2-(propan-2-yloxy)benzene, 2.58 g of <strong>[1243312-43-7]3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine</strong>, 9.4 g of caesium carbonate and 703 mg of [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), in 27 ml of dioxane and 8.8 ml of water, is microwave-heated at 130 C. for 20 minutes. The mixture is diluted with ethyl acetate and water. The aqueous phase is extracted with ethyl acetate (2*) and then with dichloromethane (2*10 ml). The combined organic phases are dried over magnesium sulfate and concentrated under vacuum. The residue is purified on 100 g of silica, elution being carried out with heptane/ethyl acetate (50/50 to 0/100), so as to obtain 2.63 g of 3-methoxy-4-[4-nitro-3-(propan-2-yloxy)phenyl]pyridine in the form of a brown solid.
2.63 g With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; water; at 130℃; for 0.333333h;Microwave irradiation; A mixture of 2.5 g of 4-bromo-1 -nitro-2-(propan-2-yloxy)benzene, 2.58 g of 3-methoxy-4- (4,4,5, 5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridine, 9.4 g of caesium carbonate and 703 mg of [1 ,1 '-bis(diphenylphosphino)ferrocene]dichloropalladium(ll), in 27 ml of dioxane and 8.8 ml of water, is microwave-heated at 130 ^ for 20 minutes. The mixture is diluted with ethyl acetate and water. The aqueous phase is extracted with ethyl acetate (2x) and then with dichloromethane (2 x 10 ml). The combined organic phases are dried over magnesium sulfate and concentrated under vacuum. The residue is purified on 100 g of silica, elution being carried out with heptane/ethyl acetate (50/50 to 0/100), so as to obtain 2.63 g of 3-methoxy-4-[4-nitro-3-(propan-2-yloxy)phenyl]pyridine in the form of a brown solid.
  • 3
  • [ 1243312-43-7 ]
  • tert-butyl N-[4-hydroxy-1-(4-iodobenzyl)-2-oxo-1,2,5,6-tetrahydropyridin-3-yl]carbonyl}glycinate [ No CAS ]
  • 2-methyl-2-propanyl N-({4-hydroxy-1-[4-(3-methoxy-4-pyridinyl)benzyl]-2-oxo-1,2,5,6-tetrahydro-3-pyridinyl}carbonyl)glycinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.24 g With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In water; N,N-dimethyl-formamide; at 120℃; for 0.333333h;Microwave irradiation; (1) Synthesis of 2-methyl-2-propanyl N-({4-hydroxy-1-[4-(3-methoxy-4-pyridinyl)benzyl]-2-oxo-1,2,5,6-tetrahydro-3-pyridinyl}carbonyl)glycinate A mixture of the compound (1.50 g) obtained in Example 2-1(1), <strong>[1243312-43-7]3-methoxy-4-pyridineboronic acid pinacol ester</strong> (870 mg), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane complex (1:1) (126 mg), 2 mol/L sodium carbonate in aqueous solution (3.4 mL) and N,N-dimethylformamide (12.3 mL) was stirred at 120C for 20 minutes under irradiation with microwaves. After cooling the reaction mixture to room temperature, a saturated aqueous solution of sodium hydrogencarbonate and ethyl acetate were added and the precipitate was recovered by filtration through Celite (registered trademark). Extraction was conducted with ethyl acetate and the combined organic layers were concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate = 20:80-0:100, then chloroform:methanol = 100:0-80:20) to give 2-methyl-2-propanyl N-({4-hydroxy-1-[4-(3-methoxy-4-pyridinyl)benzyl]-2-oxo-1,2,5,6-tetrahydro-3-pyridinyl}carbonyl)glycinate as a yellow amorphous mass (1.24 g). 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 1.49 (s, 9 H) 2.52 - 2.69 (m, 2 H) 3.32 - 3.45 (m, 2 H) 3.92 (s, 3 H) 4.00 - 4.07 (m, 2 H) 4.67 (s, 2 H) 7.22 - 7.26 (m, 2 H) 7.32 - 7.38 (m, 2 H) 7.50 - 7.60 (m, 2 H) 8.28 - 8.35 (m, 1 H) 10.18 - 10.50 (m, 1 H). MS ESI/APCI Dual posi: 468[M+H]+.
  • 4
  • [ 1243312-43-7 ]
  • [ 86953-79-9 ]
  • tert-butyl (R)-2-(3-methoxypyridin-4-yl)pyrrolidine-1-carboxylate [ No CAS ]
  • 5
  • [ 1243312-43-7 ]
  • (S)-2-((6-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)-2-phenylethan-1-ol [ No CAS ]
  • (S)-2-((6-(3-methoxypyridin-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)-2-phenylethan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 100℃; for 1h;Inert atmosphere; General procedure: The 6-iodopyrrolopyrimidine (6a - 6c, 7a - 7b or 7d) (50-350mg) was mixed with the selected arylboronic acid (1.2 eq), fine powdered K2CO3 (3 eq), XPhos (5mol %)/2nd generation XPhos precatalyst (5mol %) system or PdCl2(dppf) (5mol %) and mixture with degassed 1,4-dioxane/H2O (1/1 by vol. %, 2-8mL). The reaction was then stirred at 100C for 0.5-10h under N2 atmosphere. The solvent was removed and the product was diluted with H2O (25-100mL) and extracted with EtOAc (50-120mL), several times if required. The combined organic phases were washed with saturated aq. NaCl solution (30mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. Purification was performed as described for each individual compound.
  • 6
  • [ 1243312-43-7 ]
  • (+/-)N-((3-bromophenyl)(phenyl)methyl)-2-(trifluoromethyl)benzenesulfonamide [ No CAS ]
  • (+/-)N-((3-(3-methoxypyridin-4-yl)phenyl)(phenyl)methyl)-2-(trifluoromethyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 80℃; for 4h; General procedure: To a mixture of N-(3-bromobenzyl)-3-(trifluoromethyl)benzenesulfonamide (0.10 g, 0.25 mmol), (3,5-dimethylisoxazol-4-yl)boronic acid (72 mg, 0.51 mmol), and Na2C03 (54 mg, 0.51 mmol) in dioxane/H20 (1.6 mL/0.4 mL) was added Pd(dppf)Cl2-CH2Cl2 (21 mg, 0.025 mmol). The reaction was degassed with N2 and stirred at 80C for 4 hours. The reaction was cooled to room temperature and DCM was added. The mixture was washed with brine (IX) and water (2X). The organic layer was dried oversodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-35% EtOAc/Hexanes, 2 cycles) to afford the title compound (35 mg, 34%). LCMS(method A): m/z 411.2 (M+H)+. 'H NMR (CDCI3) delta 8.10 (s, 1H), 8.05 (d, 1H), 7.82 (d, 1H), 7.64 (t, 1H), 7.35 (t, 1H), 7.20 (d, 1H), 7.14 (d, 1H), 7.11 (s, 1H), 5.42 (t, 1H), 4.26 (d, 2H), 2.35 (s, 3H), 2.20 (s, 3H).
  • 7
  • [ 1243312-43-7 ]
  • (S)-N-(1-(3-bromophenyl)propyl)-2-(trifluoromethyl)benzenesulfonamide [ No CAS ]
  • (S)-N-(1-(3-(3-methoxypyridin-4-yl)phenyl)propyl)-2-(trifluoromethyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 80℃; for 4h; General procedure: To a mixture of N-(3-bromobenzyl)-3-(trifluoromethyl)benzenesulfonamide (0.10 g, 0.25 mmol), (3,5-dimethylisoxazol-4-yl)boronic acid (72 mg, 0.51 mmol), and Na2C03 (54 mg, 0.51 mmol) in dioxane/H20 (1.6 mL/0.4 mL) was added Pd(dppf)Cl2-CH2Cl2 (21 mg, 0.025 mmol). The reaction was degassed with N2 and stirred at 80C for 4 hours. The reaction was cooled to room temperature and DCM was added. The mixture was washed with brine (IX) and water (2X). The organic layer was dried oversodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-35% EtOAc/Hexanes, 2 cycles) to afford the title compound (35 mg, 34%). LCMS(method A): m/z 411.2 (M+H)+. 'H NMR (CDCI3) delta 8.10 (s, 1H), 8.05 (d, 1H), 7.82 (d, 1H), 7.64 (t, 1H), 7.35 (t, 1H), 7.20 (d, 1H), 7.14 (d, 1H), 7.11 (s, 1H), 5.42 (t, 1H), 4.26 (d, 2H), 2.35 (s, 3H), 2.20 (s, 3H).
  • 8
  • [ 1243312-43-7 ]
  • (S)-N-(1-(3-bromophenyl)ethyl)-3-(trifluoromethyl)benzenesulfonamide [ No CAS ]
  • (S)-N-(1-(3 -(3-methoxypyridin-4-yl)phenyl)ethyl)-3-(trifluoromethyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 80℃; for 4h; General procedure: To a mixture of N-(3-bromobenzyl)-3-(trifluoromethyl)benzenesulfonamide (0.10 g, 0.25 mmol), (3,5-dimethylisoxazol-4-yl)boronic acid (72 mg, 0.51 mmol), and Na2C03 (54 mg, 0.51 mmol) in dioxane/H20 (1.6 mL/0.4 mL) was added Pd(dppf)Cl2-CH2Cl2 (21 mg, 0.025 mmol). The reaction was degassed with N2 and stirred at 80C for 4 hours. The reaction was cooled to room temperature and DCM was added. The mixture was washed with brine (IX) and water (2X). The organic layer was dried oversodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-35% EtOAc/Hexanes, 2 cycles) to afford the title compound (35 mg, 34%). LCMS(method A): m/z 411.2 (M+H)+. 'H NMR (CDCI3) delta 8.10 (s, 1H), 8.05 (d, 1H), 7.82 (d, 1H), 7.64 (t, 1H), 7.35 (t, 1H), 7.20 (d, 1H), 7.14 (d, 1H), 7.11 (s, 1H), 5.42 (t, 1H), 4.26 (d, 2H), 2.35 (s, 3H), 2.20 (s, 3H).
  • 9
  • [ 1243312-43-7 ]
  • (+/-)methyl 2-(3-bromophenyl)-2-(3-(trifluoromethyl)phenylsulfonamido)acetate [ No CAS ]
  • methyl 2-(3-(3-methoxypyridin-4-yl)phenyl)-2-(3-(trifluoromethyl)phenylsulfonamido)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 80℃; for 4h; General procedure: To a mixture of N-(3-bromobenzyl)-3-(trifluoromethyl)benzenesulfonamide (0.10 g, 0.25 mmol), (3,5-dimethylisoxazol-4-yl)boronic acid (72 mg, 0.51 mmol), and Na2C03 (54 mg, 0.51 mmol) in dioxane/H20 (1.6 mL/0.4 mL) was added Pd(dppf)Cl2-CH2Cl2 (21 mg, 0.025 mmol). The reaction was degassed with N2 and stirred at 80C for 4 hours. The reaction was cooled to room temperature and DCM was added. The mixture was washed with brine (IX) and water (2X). The organic layer was dried oversodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-35% EtOAc/Hexanes, 2 cycles) to afford the title compound (35 mg, 34%). LCMS(method A): m/z 411.2 (M+H)+. 'H NMR (CDCI3) delta 8.10 (s, 1H), 8.05 (d, 1H), 7.82 (d, 1H), 7.64 (t, 1H), 7.35 (t, 1H), 7.20 (d, 1H), 7.14 (d, 1H), 7.11 (s, 1H), 5.42 (t, 1H), 4.26 (d, 2H), 2.35 (s, 3H), 2.20 (s, 3H).
  • 10
  • [ 1243312-43-7 ]
  • (R)-N-(1-(3-bromophenyl)ethyl)-3-(trifluoromethyl)benzenesulfonamide [ No CAS ]
  • (R)-N-(1-(3-(3-methoxypyridin- 4-yl)phenyl)ethyl)-3-(trifluoromethyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 80℃; for 4h; General procedure: To a mixture of N-(3-bromobenzyl)-3-(trifluoromethyl)benzenesulfonamide (0.10 g, 0.25 mmol), (3,5-dimethylisoxazol-4-yl)boronic acid (72 mg, 0.51 mmol), and Na2C03 (54 mg, 0.51 mmol) in dioxane/H20 (1.6 mL/0.4 mL) was added Pd(dppf)Cl2-CH2Cl2 (21 mg, 0.025 mmol). The reaction was degassed with N2 and stirred at 80C for 4 hours. The reaction was cooled to room temperature and DCM was added. The mixture was washed with brine (IX) and water (2X). The organic layer was dried oversodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-35% EtOAc/Hexanes, 2 cycles) to afford the title compound (35 mg, 34%). LCMS(method A): m/z 411.2 (M+H)+. 'H NMR (CDCI3) delta 8.10 (s, 1H), 8.05 (d, 1H), 7.82 (d, 1H), 7.64 (t, 1H), 7.35 (t, 1H), 7.20 (d, 1H), 7.14 (d, 1H), 7.11 (s, 1H), 5.42 (t, 1H), 4.26 (d, 2H), 2.35 (s, 3H), 2.20 (s, 3H).
  • 11
  • [ 1243312-43-7 ]
  • N-(1-(3-bromophenyl)cyclopropyl)-3-(trifluoromethyl)benzenesulfonamide [ No CAS ]
  • N-(1-(3-(3-methoxypyridin-4-yl)phenyl)cyclopropyl)-3-(trifluoromethyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 80℃; for 4h; General procedure: To a mixture of N-(3-bromobenzyl)-3-(trifluoromethyl)benzenesulfonamide (0.10 g, 0.25 mmol), (3,5-dimethylisoxazol-4-yl)boronic acid (72 mg, 0.51 mmol), and Na2C03 (54 mg, 0.51 mmol) in dioxane/H20 (1.6 mL/0.4 mL) was added Pd(dppf)Cl2-CH2Cl2 (21 mg, 0.025 mmol). The reaction was degassed with N2 and stirred at 80C for 4 hours. The reaction was cooled to room temperature and DCM was added. The mixture was washed with brine (IX) and water (2X). The organic layer was dried oversodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-35% EtOAc/Hexanes, 2 cycles) to afford the title compound (35 mg, 34%). LCMS(method A): m/z 411.2 (M+H)+. 'H NMR (CDCI3) delta 8.10 (s, 1H), 8.05 (d, 1H), 7.82 (d, 1H), 7.64 (t, 1H), 7.35 (t, 1H), 7.20 (d, 1H), 7.14 (d, 1H), 7.11 (s, 1H), 5.42 (t, 1H), 4.26 (d, 2H), 2.35 (s, 3H), 2.20 (s, 3H).
  • 12
  • [ 1243312-43-7 ]
  • N-(2-(3-bromophenyl)propan-2-yl)-2-nitrobenzenesulfonamide [ No CAS ]
  • N-(2-(3-(3-methoxypyridin-4-yl)phenyl)propan-2-yl)-2-nitrobenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 80℃; for 4h; General procedure: To a mixture of N-(3-bromobenzyl)-3-(trifluoromethyl)benzenesulfonamide (0.10 g, 0.25 mmol), (3,5-dimethylisoxazol-4-yl)boronic acid (72 mg, 0.51 mmol), and Na2C03 (54 mg, 0.51 mmol) in dioxane/H20 (1.6 mL/0.4 mL) was added Pd(dppf)Cl2-CH2Cl2 (21 mg, 0.025 mmol). The reaction was degassed with N2 and stirred at 80C for 4 hours. The reaction was cooled to room temperature and DCM was added. The mixture was washed with brine (IX) and water (2X). The organic layer was dried oversodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-35% EtOAc/Hexanes, 2 cycles) to afford the title compound (35 mg, 34%). LCMS(method A): m/z 411.2 (M+H)+. 'H NMR (CDCI3) delta 8.10 (s, 1H), 8.05 (d, 1H), 7.82 (d, 1H), 7.64 (t, 1H), 7.35 (t, 1H), 7.20 (d, 1H), 7.14 (d, 1H), 7.11 (s, 1H), 5.42 (t, 1H), 4.26 (d, 2H), 2.35 (s, 3H), 2.20 (s, 3H).
  • 13
  • [ 1243312-43-7 ]
  • N-(3-bromophenethyl)-2-(trifluoromethyl)benzenesulfonamide [ No CAS ]
  • N-(3-(3-methoxypyridin-4-yl)phenethyl)-2-(trifluoromethyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 80℃; for 4h; General procedure: To a mixture of N-(3-bromobenzyl)-3-(trifluoromethyl)benzenesulfonamide (0.10 g, 0.25 mmol), (3,5-dimethylisoxazol-4-yl)boronic acid (72 mg, 0.51 mmol), and Na2C03 (54 mg, 0.51 mmol) in dioxane/H20 (1.6 mL/0.4 mL) was added Pd(dppf)Cl2-CH2Cl2 (21 mg, 0.025 mmol). The reaction was degassed with N2 and stirred at 80C for 4 hours. The reaction was cooled to room temperature and DCM was added. The mixture was washed with brine (IX) and water (2X). The organic layer was dried oversodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-35% EtOAc/Hexanes, 2 cycles) to afford the title compound (35 mg, 34%). LCMS(method A): m/z 411.2 (M+H)+. 'H NMR (CDCI3) delta 8.10 (s, 1H), 8.05 (d, 1H), 7.82 (d, 1H), 7.64 (t, 1H), 7.35 (t, 1H), 7.20 (d, 1H), 7.14 (d, 1H), 7.11 (s, 1H), 5.42 (t, 1H), 4.26 (d, 2H), 2.35 (s, 3H), 2.20 (s, 3H).
  • 14
  • [ 1243312-43-7 ]
  • N-((6-bromopyridin-2-yl)methyl)-3-(trifluoromethyl)benzenesulfonamide [ No CAS ]
  • N-((3‘-methoxy-[2,4’-bipyridin]-6-yl)methyl)-3-(trifluoromethyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 80℃; for 4h; General procedure: To a mixture of N-(3-bromobenzyl)-3-(trifluoromethyl)benzenesulfonamide (0.10 g, 0.25 mmol), (3,5-dimethylisoxazol-4-yl)boronic acid (72 mg, 0.51 mmol), and Na2C03 (54 mg, 0.51 mmol) in dioxane/H20 (1.6 mL/0.4 mL) was added Pd(dppf)Cl2-CH2Cl2 (21 mg, 0.025 mmol). The reaction was degassed with N2 and stirred at 80C for 4 hours. The reaction was cooled to room temperature and DCM was added. The mixture was washed with brine (IX) and water (2X). The organic layer was dried oversodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-35% EtOAc/Hexanes, 2 cycles) to afford the title compound (35 mg, 34%). LCMS(method A): m/z 411.2 (M+H)+. 'H NMR (CDCI3) delta 8.10 (s, 1H), 8.05 (d, 1H), 7.82 (d, 1H), 7.64 (t, 1H), 7.35 (t, 1H), 7.20 (d, 1H), 7.14 (d, 1H), 7.11 (s, 1H), 5.42 (t, 1H), 4.26 (d, 2H), 2.35 (s, 3H), 2.20 (s, 3H).
  • 15
  • [ 1243312-43-7 ]
  • N-((4-bromopyridin-2-yl)methyl)-3-(trifluoromethyl)benzenesulfonamide [ No CAS ]
  • N-((3‘-methoxy-[4,4’-bipyridin]-2-yl)methyl)-3-(trifluoromethyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 80℃; for 4h; General procedure: To a mixture of N-(3-bromobenzyl)-3-(trifluoromethyl)benzenesulfonamide (0.10 g, 0.25 mmol), (3,5-dimethylisoxazol-4-yl)boronic acid (72 mg, 0.51 mmol), and Na2C03 (54 mg, 0.51 mmol) in dioxane/H20 (1.6 mL/0.4 mL) was added Pd(dppf)Cl2-CH2Cl2 (21 mg, 0.025 mmol). The reaction was degassed with N2 and stirred at 80C for 4 hours. The reaction was cooled to room temperature and DCM was added. The mixture was washed with brine (IX) and water (2X). The organic layer was dried oversodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-35% EtOAc/Hexanes, 2 cycles) to afford the title compound (35 mg, 34%). LCMS(method A): m/z 411.2 (M+H)+. 'H NMR (CDCI3) delta 8.10 (s, 1H), 8.05 (d, 1H), 7.82 (d, 1H), 7.64 (t, 1H), 7.35 (t, 1H), 7.20 (d, 1H), 7.14 (d, 1H), 7.11 (s, 1H), 5.42 (t, 1H), 4.26 (d, 2H), 2.35 (s, 3H), 2.20 (s, 3H).
  • 16
  • [ 1243312-43-7 ]
  • N-((2-bromopyridin-4-yl)methyl)-3-(trifluoromethyl)benzenesulfonamide [ No CAS ]
  • N-((3‘-methoxy-[2,4’-bipyridin]-4-yl)methyl)-3-(trifluoromethyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 80℃; for 4h; General procedure: To a mixture of N-(3-bromobenzyl)-3-(trifluoromethyl)benzenesulfonamide (0.10 g, 0.25 mmol), (3,5-dimethylisoxazol-4-yl)boronic acid (72 mg, 0.51 mmol), and Na2C03 (54 mg, 0.51 mmol) in dioxane/H20 (1.6 mL/0.4 mL) was added Pd(dppf)Cl2-CH2Cl2 (21 mg, 0.025 mmol). The reaction was degassed with N2 and stirred at 80C for 4 hours. The reaction was cooled to room temperature and DCM was added. The mixture was washed with brine (IX) and water (2X). The organic layer was dried oversodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-35% EtOAc/Hexanes, 2 cycles) to afford the title compound (35 mg, 34%). LCMS(method A): m/z 411.2 (M+H)+. 'H NMR (CDCI3) delta 8.10 (s, 1H), 8.05 (d, 1H), 7.82 (d, 1H), 7.64 (t, 1H), 7.35 (t, 1H), 7.20 (d, 1H), 7.14 (d, 1H), 7.11 (s, 1H), 5.42 (t, 1H), 4.26 (d, 2H), 2.35 (s, 3H), 2.20 (s, 3H).
  • 17
  • [ 1243312-43-7 ]
  • N-((4-bromopydin-2-yl)methyl)-2-(trifluoromethyl)benzenesulfonamide [ No CAS ]
  • N-((3‘-methoxy-[4,4’-bipyridin]-2-yl)methyl)-2-(trifluoromethyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 80℃; for 4h; General procedure: To a mixture of N-(3-bromobenzyl)-3-(trifluoromethyl)benzenesulfonamide (0.10 g, 0.25 mmol), (3,5-dimethylisoxazol-4-yl)boronic acid (72 mg, 0.51 mmol), and Na2C03 (54 mg, 0.51 mmol) in dioxane/H20 (1.6 mL/0.4 mL) was added Pd(dppf)Cl2-CH2Cl2 (21 mg, 0.025 mmol). The reaction was degassed with N2 and stirred at 80C for 4 hours. The reaction was cooled to room temperature and DCM was added. The mixture was washed with brine (IX) and water (2X). The organic layer was dried oversodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-35% EtOAc/Hexanes, 2 cycles) to afford the title compound (35 mg, 34%). LCMS(method A): m/z 411.2 (M+H)+. 'H NMR (CDCI3) delta 8.10 (s, 1H), 8.05 (d, 1H), 7.82 (d, 1H), 7.64 (t, 1H), 7.35 (t, 1H), 7.20 (d, 1H), 7.14 (d, 1H), 7.11 (s, 1H), 5.42 (t, 1H), 4.26 (d, 2H), 2.35 (s, 3H), 2.20 (s, 3H).
  • 18
  • [ 1243312-43-7 ]
  • [ 214964-87-1 ]
  • tert-butyl (2-(3-(3-methoxypyridin-4-yl)phenyl)propan-2-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 80℃; General procedure: Pd(dppf)Cl2CH2Cl2 (0.19 g, 0.23 mmol) was added into a mixture of (3- bromophenyl)methanamine hydrochloride (0.50 g, 2.3 mmol), (3,5-dimethylisoxazol-4- yl)boronic acid (640 mg, 4.5 mmol), and Na2C03 (960 mg, 9.0 mmol) in dioxane/H20 (8 mL/2 mL). The reaction was degassed with N2 and stirred at 80C overnight. After cooling to room temperature, DCM was added and the mixture was washed with brine (IX) and water (2X). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to give a crude product. Purification by silica gel chromatography (0 - 10% MeOH/DCM) afforded the title compound (0.34 g, 74%). LCMS (method A): m/z 203.2 (M+H)+.
  • 19
  • [ 1243312-43-7 ]
  • (+/-)2-(3-bromophenyl)-1-((3-(trifluoromethyl)phenyl)sulfonyl)pyrrolidine [ No CAS ]
  • 3-methoxy-4-(3-(1-((3-(trifluoromethyl)phenyl)sulfonyl)pyrrolidin-2-yl)phenyl)pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,4-dioxane; dichloromethane; water; at 85℃; for 16h;Sealed tube; A mixture of Intermediate 21 A (62 mg, 0.14 mmol) and 3-methoxy-4-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (35 mg, 0.15 mmol) in 1,4-dioxane (1.0 mL) in a Biotage microwave vessel was degassed with nitrogen for 10 minutes. To this mixture [l, l'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with DCM (11 mg, 0.014 mmol), and a sodium carbonate solution (2 M aqueous, 0.2 5mL, 0.50 mmol) were added. After degassing with nitrogen for 2 minutes, the vessel was capped and heated to 85C in a heating block for 16 hours. After cooling, the mixture was diluted with 5 mL EtOAc, and 5 mL water. The layers were separated, and the organic layer was washed with saturated sodium bicarbonate solution (10 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Purification by silica gel chromatography (20-80% EtOAc/hexanes) yielded Compound 40 (60 mg, 92%). LCMS (method A): m/z 453.3 (M+H)+. NMR (CDC13) delta 8.38 (s, 1H), 8.323 (d, 1H), 7.95 (s, 1H), 7.90 (d, 1H), 7.76 (d, 1H), 7.57 (t, 1H), 7.44 (m, 2H), 7.34 (m, 1H), 7.23 (m, 1H), 7.19 (m, 1H), 4.92 (m, 1H), 3.93 (m, 3H), 3.66 (m, 1H), 3.60 (m, 1H), 2.17 (m, 1H), 2.01-1.83 (m, 3H).
  • 20
  • [ 1243312-43-7 ]
  • N-(2-(3-bromophenyl)propan-2-yl)-3-(trifluoromethyl)benzenesulfonamide [ No CAS ]
  • N-(2-(3-(3-methoxypyridin-4-yl)phenyl)propan-2-yl)-3-(trifluoromethyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 80℃; for 4h; General procedure: To a mixture of N-(3-bromobenzyl)-3-(trifluoromethyl)benzenesulfonamide (0.10 g, 0.25 mmol), (3,5-dimethylisoxazol-4-yl)boronic acid (72 mg, 0.51 mmol), and Na2C03 (54 mg, 0.51 mmol) in dioxane/H20 (1.6 mL/0.4 mL) was added Pd(dppf)Cl2-CH2Cl2 (21 mg, 0.025 mmol). The reaction was degassed with N2 and stirred at 80C for 4 hours. The reaction was cooled to room temperature and DCM was added. The mixture was washed with brine (IX) and water (2X). The organic layer was dried oversodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-35% EtOAc/Hexanes, 2 cycles) to afford the title compound (35 mg, 34%). LCMS(method A): m/z 411.2 (M+H)+. 'H NMR (CDCI3) delta 8.10 (s, 1H), 8.05 (d, 1H), 7.82 (d, 1H), 7.64 (t, 1H), 7.35 (t, 1H), 7.20 (d, 1H), 7.14 (d, 1H), 7.11 (s, 1H), 5.42 (t, 1H), 4.26 (d, 2H), 2.35 (s, 3H), 2.20 (s, 3H).
  • 21
  • [ 7295-76-3 ]
  • [ 61676-62-8 ]
  • [ 1243312-43-7 ]
YieldReaction ConditionsOperation in experiment
Starting material 3-methoxypyridine VIII (5.0 g, 45.8 mol, 1.0 equiv.)Soluble in 100 ml of Et2O,Add 1.3 equiv. LDA in THF at -100 C.After adding the insulation reaction for 1 hour,Add isopropanol pinacol borate (11.08g, 59.5 mmol, 1.3 equiv.) after 2 hours of incubation,After quenching with water, the reaction was returned to room temperature and stirred for 1 h.Adjust the pH to between 3 and 4, spin dry the aqueous phase, and use the crude product directly for the next reaction.
  • 22
  • [ 24100-18-3 ]
  • [ 1243312-43-7 ]
  • [ 142929-15-5 ]
YieldReaction ConditionsOperation in experiment
4.75 g With bis-triphenylphosphine-palladium(II) chloride; potassium acetate; In 1,4-dioxane; water; at 100℃;Inert atmosphere; The above product <strong>[1243312-43-7]3-methoxypyridine-4-boronic acid pinacol ester</strong> XII-2 is dissolved in 100 ml of 1,4-dioxane,Add 10ml of water,Add 2-bromo-3-methoxypyridine III (8.61 g, 45.8 mmol, 1.0 equiv.)And potassium acetate (13.48g, 137.40 mmol, 3.0 equiv.),Pd(PPh3)2Cl2 (0.64 g, 0.92 mmol, 2.0 mol%),Reacting at 100 C overnight under nitrogen atmosphere,TLC showed the reaction was complete,The system was cooled to room temperature, concentrated, column chromatography,Yielding 4.75 g of a yellow solid,The total yield was 48%.
 

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