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Chemical Structure| 1244059-50-4 Chemical Structure| 1244059-50-4

Structure of 1244059-50-4

Chemical Structure| 1244059-50-4

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Product Details of [ 1244059-50-4 ]

CAS No. :1244059-50-4
Formula : C18H25BN2O4S
M.W : 376.28
SMILES Code : O=C(OC(C)(C)C)NC1=NC2=CC=C(B3OC(C)(C)C(C)(C)O3)C=C2S1

Safety of [ 1244059-50-4 ]

Application In Synthesis of [ 1244059-50-4 ]

* 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 [ 1244059-50-4 ]

[ 1244059-50-4 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 35852-81-4 ]
  • [ 1244059-50-4 ]
  • C16H18N4O2S [ No CAS ]
  • 2
  • [ 123-91-1 ]
  • [ 72287-26-4 ]
  • [ 15864-32-1 ]
  • [ 24424-99-5 ]
  • [ 96042-30-7 ]
  • [ 564483-18-7 ]
  • [ 1244059-50-4 ]
YieldReaction ConditionsOperation in experiment
With dmap; potassium acetate; Step 1: tert-Butyl (6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)carbamate A 100 mL flask charged with 2-amino-6-bromobenzothiazole (2.52 g, 10.77 mmol), bis(pinacolato)diboron (5.45 g, 21.24 mmol), potassium acetate (3.28 g, 33.09 mmol), 2-(dicyclohexylphosphino)-2',4',6'-triisopropylbiphenyl (212.2 mg, 0.436 mmol), and tris(dibenylideneacetone)dipalladium chloroform complex (117.9 mg, 0.110 mmol) was evacuated and backfilled with nitrogen. 1,4-Dioxane (20.0 mL, 233 mmol) was added and the reaction mixture stirred under a nitrogen balloon at 100° C. for 1 h. To the reaction was then added [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) chloride, complex with DCM (1:1) (285.9 mg, 0.350 mmol). After an additional 17 h the reaction mixture was cooled to room temperature, filtered through celite, rinsing with ethyl acetate, and then evaporated to dry on celite. The crude product was purified via flash chromatography on silica gel (80 g silica, solvent gradient: 0-100percent isopropyl acetate in heptanes) to yield 2.85 g. Of this material, 2.64 g was combined with di-tert-butyl dicarbonate (2.58 g, 11.45 mmol), 4-dimethylaminopyridine (79.9 mg, 0.654 mmol) and DCM (20.0 mL, 312 mmol) and stirred at room temperature for 2 h. The mixture was evaporated in vacuo and the crude product was purified via flash chromatography on silica gel (40 g silica, solvent gradient: 0-50percent ethyl acetate in heptane) to yield 2.24 g of the title compound. LCMS (ESI): [M+H]+=377.
  • 3
  • [ 72287-26-4 ]
  • [ 1244059-50-4 ]
  • 4-bromo-1-iodo-7,8,9,10-tetrahydro-6-oxa-2,10a-diazacycloocta[cd]indene [ No CAS ]
  • [ 96042-30-7 ]
  • tert-butyl (6-(4-bromo-7,8,9,10-tetrahydro-6-oxa-2,10a-diazacycloocta[cd]inden-1-yl)benzo[d]thiazol-2-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
31% With nitrogen; sodium carbonate; Step 2: tert-Butyl (6-(4-bromo-7,8,9,10-tetrahydro-6-oxa-2,10a-diazacycloocta[cd]inden-1-yl)benzo[d]thiazol-2-yl)carbamate A mixture of 4-bromo-1-iodo-7,8,9,10-tetrahydro-6-oxa-2,10a-diazacycloocta[cd]indene (1.0323 g, 2.6266 mmol), tert-butyl (6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)carbamate (2.031 g, 3.239 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) chloride, complex with DCM (1:1) (324.8 mg, 0.3977 mmol), sodium carbonate (847.5 mg, 7.92 mmol), water (3.0 mL, 170 mmol) and THF (9.0 mL, 110 mmol) was heated in a sealed vessel under nitrogen at 80° C. for 20 h. The reaction mixture was degassed by bubbling through nitrogen for 10 minutes, additional [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) chloride, complex with DCM (1:1) (523 mg) was added, and the mixture heated at 80° C. for 6 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, filtered, washed with water and brine, and evaporated in vacuo. The crude product was purified via flash chromatography on silica gel (40 g silica, solvent gradient: 0-100percent ethyl acetate in dichloromethane) to yield 0.4242 g (31percent) of the title compound as a yellow solid. LCMS (ESI): [M+H]+=514.95; 1H NMR (400 MHz, DMSO-d6) delta 11.94 (s, 1H), 8.32 (d, J=1.2 Hz, 1H), 7.84 (d, J=8.4 Hz, 1H), 7.72 (dd, J=8.3, 1.7 Hz, 1H), 7.69-7.64 (m, 1H), 7.12-7.06 (m, 1H), 4.52-4.41 (m, 2H), 4.36-4.26 (m, 2H), 2.24-2.11 (m, 2H), 1.78-1.63 (m, 2H), 1.53 (s, 9H).
 

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