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[ CAS No. 945556-96-7 ] {[proInfo.proName]}

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Chemical Structure| 945556-96-7
Chemical Structure| 945556-96-7
Structure of 945556-96-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 945556-96-7 ]

CAS No. :945556-96-7 MDL No. :
Formula : C18H27BN2O4S Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 378.29 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 945556-96-7 ]

* 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 [ 945556-96-7 ]

[ 945556-96-7 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 945556-95-6 ]
  • [ 124-63-0 ]
  • [ 945556-96-7 ]
YieldReaction ConditionsOperation in experiment
80% With pyridine In dichloromethane at 0 - 20℃; I Charge a round bottom flask with l-isopropyl-3-(4,4,5,5-tetramethyl- [l,3,2]dioxaborolan-2-yl)-lH-indol-6-ylamine (11.83 g, 39.43 mmol), dichloromethane (400 mL) and pyridine (6.40 mL, 78.87 mmol). Cool the resulting solution to O0C; while stirring slowly add methanesulfonyl chloride (12.20 mL, 157.73 mmol). Allow the reaction to stir overnight and reach ambient temperature. Quench the reaction with saturated aqueous sodium bicarbonate. Extract the resulting aqueous layer with dichloromethane. Combine the combined extracts and wash the combined extracts with saturated aqueous sodium bicarbonate, water and brine, dry over sodium sulfate and concentrate in vacuo. Purify the resulting solid on a by flash chromotography (silica gel; 65%-100% dichloromethane gradient in hexane then gradient to 2.5% ethyl acetate in dichloromethane) to provide 12.0 g (80%) of the product as a light pink solid foam. 1H NMR (CDCl3) δ 7.96 (d, IH, J = 8.4 Hz), 7.69 (s, IH), 7.39 (d, IH, J = 1.9 Hz), 6.88 (dd, IH, J = 8.4 Hz, 1.9 Hz), 6.38 (br s, IH), 4.56 (septet, IH, J = 6.8 Hz), 2.91 (s, 3H), 1.49 (d, 6H, J = 6.8 Hz), 1.34 (s, 12H); MS (IS-) m/e 377 (M - 1).
  • 2
  • [ 2873-18-9 ]
  • [ 945556-96-7 ]
  • N-[3-(5-chloro-thiophen-2-yl)-1-isopropyl-1H-indol-6-yl]-methanesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100℃; Place N-[l-isopropyl-3-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-lH-indol-6-yl]- methanesulfonamide (266 mg, 0.70 mmol), potassium carbonate (242 mg, 1.75 mmol), 2-bromo-5-chloro- thiophene (207 mg, 1.05 mmol), dioxane (6 mL) and water (1 mL), followed by addition of tetrakis(trirhohenylphosphine) palladium (0) (20 mg, 0.018 mmol) in a sealed tube under nitrogen. Heat the reaction mixture at 1000C overnight, then cool to room temperature. Dilute the reaction mixture with ethyl acetate, and sequentially wash the resulting mixture with water and brine. Dry the organic layer over <n="23"/>MgSO4. Chromatograph the crade residue on silica gel column eluting with hexane and ethyl acetate (gradient) to give 89 mg (34%) of the title compound. 1HNMR (CDCl3) delta 7.79 (d, IH, J= 8.8 Hz), 7.42 (d, IH, J= 1.8 Hz), 7.35 (s, 1 H), 6.97 (dd, IH, J= 2.0, 8.6 Hz), 6.93 (d, IH, J= 4.0 Hz), 6.88 (d, IH, J= 4.0 Hz), 4.50-4.67 (m, IH), 2.97 (s, 3H), 1.52 (d, 6H, J= 6.6 Hz).
  • 3
  • [ 945556-96-7 ]
  • [ 41963-20-6 ]
  • N-[3-(4-cyano-2-methyl-phenyl)-1-isopropyl-1H-indol-6-yl]-methanesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With potassium phosphate; 2?-(diphenylphosphino)-N,N?-dimethyl-(1,1?-biphenyl)-2-amine;palladium diacetate; In 1,4-dioxane; at 150℃; for 0.25h;Microwave irradiation; AddN-[l-isoprorhoyl-3-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-lH-indol-6-yl]- methanesulfonamide (50.0 mg, 0.132 mmoles), <strong>[41963-20-6]4-bromo-3-methyl-benzonitrile</strong> (51.8 mg, 0.264 mmoles), Pd(OAc)2 (4.25 mg, 0.018 mmoles; 4.25 mg), 2-(diphenylphosphino)-2'-(N,N-dimethylamino)biphenyl (11.5 mg, 0.030 mmoles), potassium phosphate (84.2 mg, 0.396 mmoles), and 1,4-dioxane (1.00 mL) to a 10 mL microwave vessel, equipped with a stir bar. Purge the reaction mixture with nitrogen, and then seal the vessel with a cap. Place the vessel in a microwave reactor at 15O0C for 15 min at 250 W heating. Monitor the reaction using LC/MS. Cool the reaction to ambient temperature and quench with saturated aqueous ammonium chloride. Extract the resulting mixture into ethyl acetate. Wash the combined extracts with saturated aqueous ammonium chloride, water and brine. Dry the resulting solution over sodium sulfate (granular) and concentrate in vacuo. Disssolve the resulting solid in dichloromethane and purify on a chromatotron (IMM silica gel plate) 0-2percent ethyl acetate gradient in dichloromethane. A second purification may be necessary. This time purify the material with 30-40percent ethyl acetate gradient in hexane to provide N-[3-(4-Cyano-2-methyl-phenyl)-l-isoprorhoyl-lH-indol-6-yl]-methanesulfonamide, 35 mg (75percent) as an off white solid. 1HNMR (CDCl3) delta 7.58 (s, IH), 7.45-7.52 (m, 3H), 7.41 (d, IH, J = 8.4Hz), 7.25 (s, IH), 6.9 (dd, IH, J = 8.4, 1.7Hz), 6.52 (s, IH), 4.65 (septet, IH, J = 6.7Hz), 2.98 ( s, 3H), 2.34 (s, 3H), 1.55(d, 6H, J = 6.7Hz); MS (IS-) m/e 377 (M - 1).
  • 4
  • [ 886373-28-0 ]
  • [ 945556-96-7 ]
  • N-[3-(6-cyano-5-fluoro-pyridin-3-yl)-1-isopropyl-1H-indol-6-yl]-methanesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With potassium phosphate; tricyclohexylphosphine;tris-(dibenzylideneacetone)dipalladium(0); In 1,4-dioxane; at 100℃; for 18h; Bubble N2 through a mixture of N-[I -isopropyl-3 -(4,4,5, 5-tetramethyl- [l,3,2]dioxaborolan-2-yl)-lH-indo-6-yl]-methanesulfonamide (0.186g, 0.493 mmol), 5-bromo-2-cyano-3- <n="24"/>fluoropyridine (0.090 g, 0.448 mmol), K3PO4 (1.3 M) (0.60 ml), and dioxane (1.2 ml) for 5 minutes. Add tricyclohexylphosphine (3.0 mg, 0.011 mmol) and Pd2(dba)3 (4.1 mg, 0.0045 mmol). Seal the tube and stir at 1000C for 18h. After cooling to room temperature, extract with EtOAc and wash with NaHCO3. Dry the organic phase with MgStheta4. Purify the crude residue using silica gel chromatography to give 0.112g (67% yield) of the title compound, MS: 373.0 (M+H)
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