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Chemical Structure| 1202765-56-7 Chemical Structure| 1202765-56-7

Structure of 1202765-56-7

Chemical Structure| 1202765-56-7

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Product Details of [ 1202765-56-7 ]

CAS No. :1202765-56-7
Formula : C12H14BrNO
M.W : 268.15
SMILES Code : BrC1=CC2=C(C=C1)C3(CCOCC3)CN2
MDL No. :MFCD19703314

Safety of [ 1202765-56-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 1202765-56-7 ]

* 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 [ 1202765-56-7 ]

[ 1202765-56-7 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 1190861-43-8 ]
  • [ 1202765-56-7 ]
YieldReaction ConditionsOperation in experiment
73% LiAIH4 (0.54 g, 14.18 mmol) was added portion wise at 0C to a solution of 178a (1.6 g, 5.67 mmol) in THF (500 mL). The reaction mixture was heated at 80C for 4 h, cooled, then sequentially quenched with water (0.54 mL), 20% NaOH solution (0.54 mL) and water (1.08 mL) and stirred for 1H at RT. The mixture was filtered through a plug of celite and the filter was rinsed with DCM/MeOH = 4: 1 (3x 50 mL). The filtrate was evaporated and the residue was purified by flash column chromatography [silica gel; hexane /EtOAc 4:1 ]. Light yellow solid. Yield: 1.1 g (73%). HPLC (method 1 ): Rt = 3.27 min, m/z [M+H]+ = 270.2 (MW calc. 268.15).
64% A heterogeneous mixture of 6-bromo-2',3',5',6'-tetrahydrospiro[indole-3,4l-pyran]-2(lH)-one A.99 (3.5 g, 12.4 mmol) in toluene (25 mL) was stirred at 80 0C. To the heated mixture was added a solution of Red- Al (65% in toluene, 11.6 mL, 37.2 mmol) and the mixture was stirred at 800C. After 50 min, the mixture was cooled to 0 0C and quenched with 2 N of aqueous NaOH (31 mL, 62 mmol) with stirring. The mixture was extracted with ethyl acetate (100 mL, 2 times). The combined extracts were washed with brine (100 mL, 3 times), dried (Na2SO4), filtered, and concentrated under reduced pressure to give a green solid. The product was purified by silica gel column chromatography using using 0 to 100% gradient of dichloromethane-methanol-NH4OH (89:9:1) in dichloromethane) to give 6-bromo- 1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-pyran] A.100 (2.13 g, 64%) as a yellow solid: 1H NMR (500 MHz, DMSO-dbeta) delta ppm 6.91 - 6.99 (1 H, m), 6.66 (1 H, dd, J=7.8, 1.7 Hz), 6.59 (1 <n="63"/>H, d, J=I .7 Hz), 5.85 (1 H, s), 3.70 - 3.87 (2 H, m), 3.36 - 3.51 (4 H, m), 1.65 - 1.84 (2 H, m), 1.39 - 1.57 (2 H, m); ESI-MS m/z 268.0 [(M+l) (79Br)] and 270.0 [(M+l) (81Br)].
With sodium bis(2-methoxyethoxy)aluminium dihydride; In toluene; at 80℃; for 0.833333h; A heterogeneous mixture of 6-bromo-2',3',5',6'-tetrahydrospiro[indoline-3,4'- pyran]-2-one (3.5 g, 12.4 mmol) in toluene (25 mL) was stirred at 80 C. To the heated mixture was added a solution of Red- Al (65% in toluene, 11.6 mL, 37.2 mmol) and the mixture was stirred at 80 C for 50 min. After this time the mixture was cooled to 0 C and quenched with a 2 N solution of aqueous NaOH (31 mL, 62 mmol). The mixture was extracted with EtOAc (2 x 100 mL). The combined extracts were washed with brine (3 x 100 mL), dried over Na2SO4, filtered, and evaporated in vacuo. The resulting residue was purified by column chromatography (0 to 100% gradient OfDCM-MeOH-NH4OH (89:9:1) in DCM) to give 6-bromo-2',3',5',6'-tetrahydrospiro[indoline-3,4'-pyran] as a yellow solid. Mass Spectrum (ESI) m/e 268 [(M+l) (79Br)] and 270 [(M+l) (81Br)].
 

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