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[ CAS No. 756520-72-6 ] {[proInfo.proName]}

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Chemical Structure| 756520-72-6
Chemical Structure| 756520-72-6
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Product Details of [ 756520-72-6 ]

CAS No. :756520-72-6 MDL No. :MFCD26937568
Formula : C15H22BNO4S Boiling Point : -
Linear Structure Formula :- InChI Key :PYVUDSAMLHAQCJ-UHFFFAOYSA-N
M.W : 323.22 Pubchem ID :21111381
Synonyms :

Safety of [ 756520-72-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 756520-72-6 ]

* 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 [ 756520-72-6 ]

[ 756520-72-6 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 71703-16-7 ]
  • [ 73183-34-3 ]
  • [ 756520-72-6 ]
YieldReaction ConditionsOperation in experiment
68% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃; for 2.5h; Tributyl(thiazol-4-yl)stannane Synthesis of 3-Methyl-7 -(4,4,5, 5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 ,2,4,5-tetrahydro- 3-benzazepine 4.3 General procedure: Tributyl(thiazol-4-yl)stannane Synthesis of 3-Methyl-7 -(4,4,5, 5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 ,2,4,5-tetrahydro- 3-benzazepine 4.3100 mg of 7-bromo-3-methyl-1 ,2,4,5-tetrahydro-3-benzazepine, 127 mg bis-(pinacolato)- diboron, 20 mg 1 , -bis(diphenylphospino)ferrocenedichloropalladium(ll) and 123 mg potassium acetate were suspended in 2 mL dioxane and the mixture stirred at 100 °C for 1 .25 h. The mixture was diluted after cooling with dioxane, filtered through Celite, washed with dioxane and the solvent was evaporated in vacuo to yield 220 mg (92 %, content 50 %) 3-methyl-7-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 ,2,4,5-tetrahydro-3-benzazepine 4.3 as solid, which was used in the next step without further purification.
With potassium acetate In N,N-dimethyl-formamide at 80℃; for 1 - 2h; 15.C Crude 15-C-2 (0.156g, 0.566 mmol ), potassium acetate (0.167g, 1.698mmol), bis(pinacolato)diboron (0.144g, 0.509 mmol), and PdCl2(dppf) (0.046g, 0.0566mmol) were added to a round bottom flask. Dry DMF (10 ml) was then added and the flask was flushed with nitrogen. The resultant mixture was stirred and placed into an 8O0C oil bath. The reaction was followed by LCMS. Upon consumption of starting material (l-2hr), the reaction mixture was diluted with ethyl acetate, washed twice with water and twice with brine. The resultant organic solution was then dried over MgSO4 and concentrated to afford the crude boronate ester 15-C-3, which was used directly for the next step without further purification. The Suzuki coupling was carried out using the standard conditions already described with the Boykin catalyst. See example 15-36 as product.
  • 2
  • [ 1633-82-5 ]
  • [ 214360-73-3 ]
  • [ 756520-72-6 ]
YieldReaction ConditionsOperation in experiment
70% Stage #1: 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline With triethylamine In dichloromethane at 0℃; for 0.0833333h; Stage #2: 3-chloro-n-propanesulfonyl chloride In dichloromethane at 0 - 70℃; for 3h; I.240.1 4- (4, 4, 5, 5-Tetramethyl-1, 3, 2-dioxaborolan-2-yl)aniline (5 g, 22. 8 MMOL) WAS DISSOLVED in DCM (100 mL, 0. 2M), triethylamine (15 mL, 5. 0 molar EQUIVALENT) WAS ADDED to the mixture. The reaction was stirred at 0oC for 5 min. 3-chloropoane-1-sulfonyl chloride (4. 2 G, 23. 0 MMOL) was added portion wise. The reaction was stirred at 0 C for 1 hr and brought gradually to room temperature, heated to reflux at 70oC for 2 hr. The mixture was cooled to room temperature, diluted with EtOAc and water. The organic layer was washed with brine, dried over MGS04, filtered, and concentrated. The residue was purified through a silica column to afford 2- [4- (4, 4, 5, 5-TETRAMETHYL-1, 3, 2-dioxaborolan-2- yl)phenyl]isothiazolidine 1,1-dioxide as off-white solid (5. 2 G, 70% yield). 1H NMR (400 MHz, DMSO-d6) 6 7. 62 (d, 2H), 7. 18 (d, 2H), 3. 76 (T, 2H), 3.53 (t, 2H), 2.41 (t, 2H), 1. 28 (s, 12H).
  • 3
  • [ 756520-72-6 ]
  • [ 1533423-93-6 ]
  • N3-[2,6-dichloro-4'-(1,1-dioxo-1λ6-isothiazolidin-2-yl)biphenyl-4-yl]-1H-[1,2,4]-triazole-3,5-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
12% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 100℃; for 16h; Inert atmosphere; Sealed tube; N-3-[2,6-Dichloro-4'-(1,1-dioxo-1,6-isothiazolidin-2-yl)biphenyl-4-yl]-1H-[1,2,4]-triazole-3,5-diamine (Compound 289) To a mixture of N3-(4-bromo-3,5-dichlorophenyl)-lH-l,2,4-triazole-3,5-diamme Intermediate 2 (100 mg, 310 iimol, Eq: 1.00), 2-[4-(4,4,5,5-Tetramethyl-[l,3,2]dioxaborolan-2-yl)-phenyl]- isothiazolidinc 1,1 -dioxide ( 150 mg, 464 iimol, Eq : 1.5) andtetrakis(triphenylphosphine)palladium (0) (28.6 mg, 24.8 iimol, Eq: 0.08) was added degassed (nitrogen bubbling with sonication) dry dioxane (1.96 ml) and a degassed (nitrogen bubbling with sonication) solution of potassium Carbonate in water (2M, 310 μ, 619 iimol, Eq: 2). The reaction mixture was sealed and stirred at 100 C for 16h.The reaction mixture was adsorbed unto silica (0.6 g) and purified on silicagel (column 12 g, dichlo ro m e t h a n e m e t h a n o 1100:0 to 70:30). One fraction was isolated and dried in vacuo to afford 119 mg of a yellow solid. The yellow solid was further purified on reverse phase HI. PC (CN column). One fraction was isolated to afford 16 mg (12%) of the desired product as a brown solid. MS +m/z: 439.1 (M+H)
  • 4
  • [ 756520-72-6 ]
  • (4R)-4-[(1R)-1-[(5-bromo-2-methyl-1,3-benzothiazol-7-yl)oxy]ethyl]pyrrolidin-2-one [ No CAS ]
  • (4R)-4-[(1R)-1-[[5-[4-(1,1-dioxo-1,2-thiazolidin-2-yl)phenyl]2-methyl-1,3-benzothiazol-7-yl]oxy]ethyl]pyrrolidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 95℃; for 16h; Synthesis of (4R)-4-[(1 R)-1 -[[2-Methyl-5-[6-(trifluoromethyl)-3-pyridyl]-1 ,3-benzothiazol- 7-yl]oxy]ethyl]pyrrolidin-2-one (Example 4) General procedure: Synthesis of (4R)-4-[(1 R)-1 -[[2-Methyl-5-[6-(trifluoromethyl)-3-pyridyl]-1 ,3-benzothiazol- 7-yl]oxy]ethyl]pyrrolidin-2-one (Example 4)To a mixture of 90 mg (4R)-4-[(1 R)-1 -[(5-bromo-2-methyl-1 ,3-benzothiazol-7-yl)oxy]ethyl] pyrrolidin-2-one 1A_, 58 mg [6-(trifluoromethyl)-3-pyridyl]boronic acid 4.29 and 250 μΙ_ 2M aqueous sodium carbonat solution in 2 mL dioxane was added 8.9 mg 1 , - bis(triphenylphosphine)palladium(ll) chloride. The reaction mixture was stirred at 80 °C for 3 h. The reaction mixture was poured into water and extracted with ethly acetate. The combined organic phases were dried and concentrated in vacuo. The crude residue was purified by rpHPLC to yield 49 mg (yield: 46 %) of Example 4.
YieldReaction ConditionsOperation in experiment
93% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 100 - 130℃; Inert atmosphere; Microwave irradiation; 1 -[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-[4-(4,4,5,5-tetramethyl-[1 ,3,2]di (0540) phenyl]-imidazolidin-2-one (B2) General procedure: A mixture of 1 -(4-bromo^henyl)-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-imidazolidin-2-one (1 .16 g, 2.9 mmol), bis(pinacolato)diboron (1 .10 g, 4.35 mmol), Pd(dppf)Cl2.DCM (237 mg, 0.29 mmol), KOAc (854 mg, 8.7 mmol) and 1 ,4-dioxane (15 ml_) was de-oxygenated with nitrogen for 10 minutes then heated in the microwave at 130°C for 1 h. The mixture was filtered through celite, with further methanol washing, then concentrated in vacuo. The crude material was partitioned between DCM (50 ml_) and water (50 ml_), passed through a phase separator, concentrated in vacuo then purified by silica gel chromatography, eluting with 0-100% EtOAc / /'so-hexane, to afford 1 -[2-(tert- butyl-dimethyl-silanyloxy)-ethyl]-3-[4-(4,4,5,5-tetramethyl-[1 ,3,2]dioxabolan-2-yl)-phenyl]- imidazolidin-2-one (B2) as a cream solid (817 mg, 1 .83 mmol, 63%); LC-MS. Rt 3.80 min, AnalpH2_MeOH_4min(1 ); (ESI+) m/z 447.3 [M+H]+
  • 6
  • [ 756520-72-6 ]
  • C12H8IN3O [ No CAS ]
  • C21H18N4O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
9% With potassium phosphate; methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) In 1,4-dioxane; water at 90℃; for 1h; Inert atmosphere; Microwave irradiation; Ex-167.6 5-(4-(3-hydroxy-3-methylbutoxy)phenyl)-7-phenyl-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimid 4-one (Ex-163) General procedure: 5-(4-(3-hydroxy-3-methylbutoxy)phenyl)-7-iodo-3,5-dihydro-4H-pyrrolo[3,2-d]pyri (0909) (CH18) (150 mg, 0.341 mmol), phenylboronic acid (62.4 mg, 0.512 mmol), K3PO4 (145 mg, 0.682 mmol), PdXPhosG3 (14.4 mg, 0.017 mmol) in 1 ,4-dioxane:H20 (3 mL, 4:1) was de-oxygenated with N2 for 5 min and then heated in a microwave reactor at 90°C for 1 h. The reaction mixture was filtered through a Si-thiol cartridge (1 g) and washed with MeOH (3 x CV) followed by DCM (3 x CV). The filtrate was evaporated to dryness and the crude residue was purified by purified by silica gel column chromatography eluting with 0-5% MeOH/DCM followed by reversed phase preparative HPLC to afford 5-(4-(3-hydroxy-3-methylbutoxy)phenyl)-7-phenyl-3,5-dihydro-4H-pyrrolo[3,2- d]pyrimidin-4-one (Ex-163) as a white solid (46 mg, 35%); LC-MS. Rt 8.20 min, (0910) AnalpH2_MeOH_QC_V1 (1); (ESI+) m/z 390.3 [M+H]+; NMR (400 MHz, DMSO-c/6): 12.13 (br-s, 1 H), 8.15-8.13 (m, 2H), 8.07 (s, 1 H), 7.97 (s, 1 H), 7.46 (d, J = 8.7 Hz, 2H), 7.42-7.37 (m, 2H), 7.25- 7.22 (m, 1 H), 7.02 (d, J = 8.7 Hz, 2H), 4.43 (s, 1 H), 4.15 (t, J = 7.1 Hz, 2H), 1 .88 (t, J = 7.1 Hz, 2H), 1 .19 (s, 6H).
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