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Chemical Structure| 710348-41-7 Chemical Structure| 710348-41-7

Structure of 710348-41-7

Chemical Structure| 710348-41-7

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Product Details of [ 710348-41-7 ]

CAS No. :710348-41-7
Formula : C8H12BNO4S
M.W : 229.06
SMILES Code : O=S(NC1=CC(B(O)O)=CC=C1)(CC)=O
MDL No. :MFCD10699609
InChI Key :UODGYEZPCAFKEA-UHFFFAOYSA-N
Pubchem ID :46738824

Safety of [ 710348-41-7 ]

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

Application In Synthesis of [ 710348-41-7 ]

* 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 [ 710348-41-7 ]

[ 710348-41-7 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 405554-89-4 ]
  • [ 710348-41-7 ]
  • C28H34N4O3SSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 90.0℃;Inert atmosphere; Synthetic Method J[00232] Step 1 : 4-(5 -Bromo-2-phenyl- 1 -((2-(trimethylsilyl)ethoxy)methyl)- 1 H- imidazol-4-yl)pyridine (130 mg, 0.301 mmol) was dissolved in DME (3.0 mL) and 2M aqueous sodium carbonate (0.586 mL) and degassed with nitrogen for 1 minute. The appropriate phenylboronic acid (1.3 eq.) and palladium tetrakistriphenylphosphine (17.4 mg, 0.015 mmol) were added and the reaction was placed in an oil bath heated to 90 C. The crude mixtures were loaded onto a pre-packed silical gel pre-column and purified by chromatography using a gradient of 0-10% MeOH/DCM. Compounds were >90-95% pure.
  • 2
  • [ 710348-41-7 ]
  • 4-bromo-2-methyl-6-(6-methylpyridin-3-yl)isoquinolin-1-one [ No CAS ]
  • N-[3-[2-methyl-6-(6-methylpyridin-3-yl)-1-oxoisoquinolin-4-yl]phenyl]ethanesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
14.1% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In 1,4-dioxane; water; at 100.0℃; for 1.0h;Microwave irradiation; A mixture of 4-bromo-2-methyl-6-(6-methylpyridin-3-yl)isoquinolin-1-one (135 mg, 0.41 mmol), <strong>[710348-41-7][3-(ethylsulfonylamino)phenyl]boronic acid</strong> (141 mg, 0.62 mmol), Pd(dppf)Cl2 (35 mg, 0.05 mmol) and aqueous 1M K3PO4 (1.03 mL) in dioxane (6 mL) was microwaved at 100 C. for 1 h. Purification by silica gel chromatography (PE:EA=3:1 to 1:2) followed by preparative HPLC gave the title compound (25 mg, 14.1%) as a white solid. 1H NMR (CDCl3, 400 MHz) delta 8.74 (d, J=2.0 Hz, 1H), 8.41 (d, J=8.4 Hz, 1H), 7.96 (d, J=8.0 Hz, 1H), 7.86 (d, J=8.8 Hz, 1H), 7.75 (s, 1H), 7.58 (s, 1H), 7.47 (t, J=8.0 Hz, 1H), 7.39 (s, 1H), 7.35 (d, J=8.4 Hz, 1H), 7.30 (d, J=8.4 Hz, 1H), 7.24 (d, J=8.4 Hz, 1H), 3.59 (s, 3H), 3.59 (s, 3H), 3.15 (q, J=7.2 Hz, 2H), 1.19 (t, J=7.2 Hz, 3H). LCMS: 434.1 (M+H)+.
  • 3
  • [ 710348-41-7 ]
  • 4-bromo-2-methyl-6-pyridin-2-ylisoquinolin-1-one [ No CAS ]
  • N-[3-(2-methyl-1-oxo-6-pyridin-2-ylisoquinolin-4-yl)phenyl]ethanesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
3.9% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In 1,4-dioxane; water; at 80.0℃; for 0.333333h;Microwave irradiation; Inert atmosphere; Step 4: For 5 min, N2 was bubbled through a mixture of 4-bromo-2-methyl-6-pyridin-2-ylisoquinolin-1-one (48.1 mg, 0.153 mmol), <strong>[710348-41-7][3-(ethylsulfonylamino)phenyl]boronic acid</strong> (35.0 mg, 0.153 mmol), Pd(dppf)Cl2 (22.3 mg, 0.03 mmol) and aqueous 1M K3PO4 (0.38 mL, 0.38 mmol, 1 M) in dioxane (5 mL) which was then microwaved at 80 C. for 20 min. Purification by silica gel chromatography (PE:EA=3:1 to 1:2) followed by preparative HPLC gave the title compound (2.5 mg, 3.9%) as a white solid. 1H NMR (Methanol-d4, 400 MHz) delta 8.69 (d, J=8.4 Hz, 1H), 8.59 (d, J=8.4 Hz, 1H), 8.23 (d, J=1.2 Hz, 1H), 8.15-8.22 (m, 1H), 8.10 (dd, J1=8.4 Hz, J2=1.6 Hz, 2H), 7.65-7.62 (m, 1H), 7.50-7.45 (m, 3H), 7.38-7.30 (m, 2H), 3.71 (s, 3H), 3.16 (q, J=7.2 Hz, 2H), 1.32 (t, J=7.2 Hz, 3H). LCMS: 420.1 (M+H)+
  • 4
  • [ 710348-41-7 ]
  • 4-chloro-2-methyl-2,6-naphthyridin-1-one [ No CAS ]
  • N-[3-(2-methyl-1-oxo-2,6-naphthyridin-4-yl)phenyl]ethanesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
6.8% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In 1,4-dioxane; water; at 120.0℃; for 2.0h; A mixture of 4-chloro-2-methyl-2,6-naphthyridin-1-one (50.0 mg, 0.26 mmol), <strong>[710348-41-7][3-(ethylsulfonylamino)phenyl]boronic acid</strong> (88.0 mg, 0.38 mmol), Pd(dppf)Cl2 (15.3 mg, 0.026 mmol) and K3PO4 (190 mg, 0.9 mmol) in dioxane (3 mL) and water (0.5 mL) was microwaved at 120 C. under microwave for 2 h. Purification by silica gel chromatography on (PE:EA=10:1 to 1:1) followed by preparative HPLC gave the title compound (5.9 mg, 6.8%) as a yellow solid. 1H NMR (Methanol-d4, 400 MHz) delta 8.99 (brs, 1H), 8.71 (d, J=6.0 Hz, 1H), 8.39 (d, J=5.6 Hz, 1H), 7.62 (s, 1H), 7.51 (t, J=8.0 Hz, 1H), 7.41-7.40 (m, 1H), 7.36 (dd, J1=8.0 Hz, J2=1.2 Hz, 1H), 7.29 (d, J=5.6 Hz, 1H), 3.72 (s, 3H), 3.17 (q, J=7.6 Hz, 2H), 1.35 (t, J=7.6 Hz, 3H). LCMS: 344.1 (M+H)+.
  • 5
  • [ 710348-41-7 ]
  • 7-chloro-N-[(4-ethoxy-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]-1-isopropylimidazo[1,5-a]pyridine-5-carboxamide [ No CAS ]
  • N-[(4-ethoxy-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]-7-{3-[(ethylsulfonyl)-amino]phenyl}-1-isopropylimidazo[1,5-a]pyridine-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; ethanol; water; at 110.0℃; for 1.0h;Inert atmosphere; Microwave irradiation; 100 mg (0.2Smmol) 7-chloro-N- [(4-ethoxy-6-methyl-2-oxo- 1 ,2-dihydropyridin-3-yl)methyl] -1-isopropylimidazo[1,5-a]pyridine-5-carboxamide (intermediate 201A), 62.5 mg (0.27 mmol) {3-[(ethylsulfonyl)amino]phenyl }boronic acid and 29 mg (25 pmol)tetrakis(triphenylphosphine)palladium(0) were weighed into a microwave vial under an atmosphere of argon. 0.25 ml (0.5 mmol) aqueous sodium carbonate solution (2N), 1.5 ml ethanol und 1.5 ml1 ,2-dimethoxyethane was added and the resulting mixture heated for lh to 110 C in a Biotage Initiator microwave oven. The reaction mixture was concentrated in vacuo and the residue redissolved in dimethylsulfoxide, filtered and purified by HPLC (preparative HPLC conditions 1) to yield 50 mg (36%) of the target compound.?H NMR (400 MHz, DMSO-d6) oe [ppm] = 1.22 (t, 3 H), 1.26 (q, 3 H), 1.32 (d, 6 H), 2.17 (s, 3 H),3.14 (q, 2 H), 3.44 (sept., 1 H), 4.1 (q, 2 H), 4.35 (dd, 2 H), 6.09 (s, 1 H), 7.24 (d, 1 H), 7.37 (s, 1 H), 7.43 (t, 1 H), 7.54 (d, 1 H), 7.92 (s, 1 H), 8.77 (t, 1 H), 8.82 (s, 1 H), 9.84 (s, 1 H), 11.46 (s, 1H)LCMS (condition 2.3): R 0,94 mm; MS (ESI): [M + H] = 552.
  • 6
  • [ 1262618-38-1 ]
  • [ 710348-41-7 ]
  • C15H15N5O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,4-dioxane; water; at 90.0℃; for 6.0h;Inert atmosphere; A mixture of compound 3 (4mmol), <strong>[710348-41-7](3-(ethylsulfonamido)phenyl)boronic acid</strong> (4.8mmol), [1,1?-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (5mol %), and sodium carbonate (12mmol) in 1,4-dioxane (10mL) and water (5mL) was heated under nitrogen conditions (90C, 6h). After cooling to ambient temperature, the reaction mixture was filtered and concentrated. The residue was partitioned between water and dichloromethane. The organic layer was separated and purified by flash chromatography to get compound 3b (78%). (0029) 3b: Light yellow powder, 78% yield. 1H NMR (400MHz, Chloroform-d, delta ppm) 9.01 (d, J=1.7Hz, 1H), 8.72 (d, J=1.7Hz, 1H), 7.57-7.50 (m, 2H), 7.44-7.39 (m, 1H), 7.35-7.30 (m, 1H), 6.94 (s, 1H), 3.22 (q, J=7.4Hz, 2H), 2.74 (s, 3H), 1.43 (t, J=7.4Hz, 3H). ESI-HRMS m/z: 362.0923, [M+1] +, calcd for C15H15N5O4S: 361.0845.
  • 7
  • [ 710348-41-7 ]
  • 6-bromo-3-methyl-[1,2,4]triazolo[4,3-a]pyridin-8-amine [ No CAS ]
  • C15H17N5O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,4-dioxane; water; at 90.0℃; for 6.0h;Inert atmosphere; General procedure: A mixture of compound 67 4 (2mmol), boric acids or borates (2.4mmol), 68 [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (5mol %), and 69 sodium carbonate (6mmol) in 11 1,4-dioxane (8mL) and 56 water (4mL) was heated under nitrogen conditions (90C, 6h). After cooling to ambient temperature, the reaction mixture was filtered and concentrated. The residue was partitioned between water and dichloromethane. The aqueous layer was extracted with dichloromethane three additional times. The combined organic layers were washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography to provide compounds 5a-q.
 

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