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Chemical Structure| 1301610-33-2 Chemical Structure| 1301610-33-2

Structure of 1301610-33-2

Chemical Structure| 1301610-33-2

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Product Details of [ 1301610-33-2 ]

CAS No. :1301610-33-2
Formula : C17H21NO2
M.W : 271.35
SMILES Code : O=C(OC(C)(C)C)NC1(C2=CC=C(C#C)C=C2)CCC1

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Application In Synthesis of [ 1301610-33-2 ]

* 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 [ 1301610-33-2 ]

[ 1301610-33-2 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 120315-65-3 ]
  • [ 1301610-33-2 ]
  • [ 1301610-92-3 ]
YieldReaction ConditionsOperation in experiment
47% With triethylamine;copper(l) iodide; bis(tri-t-butylphosphine)palladium(0); at 0 - 20℃; for 18h;Inert atmosphere; Step 1: tert-Butyl (1-(4-((4-cyano-2-methoxyphenyl)ethynyl)phenyl)cyclobutyl)carbamate: To a solution of <strong>[120315-65-3]4-bromo-3-methoxybenzonitrile</strong> (1.92 g, 7.075 mmol) in anhydrous triethylamine (8 mL) and 1 ,4-dioxane (8 mL) was added bis(tert- butylphosphine)palladium(O) (0.144g, 0.283mmol) and copper(l) iodide (13 mg,0.094mmol). The reaction mixture was then degassed with N2 for 10 minutes before being cooled to 0°C. A solution of ferf-butyl 1 -(4-ethynylphenyl)cyclobutylcarbamate (1.00 g, 4.72 mmol) in TEA (8 mL) was added dropwise to the cooled reaction mixture. The reaction was allowed to warm to RT and stirred for 18 hours. The reaction mixture was concentrated in vacuo and the residue diluted with DCM (20 mL) and filtered through Celite. The resulting filtrate was concentrated in vacuo to afford a brown oil that was purified by silica gel chromatography (ethyl acetate/hexane gradient, 0-->50percent) yielding the title compound as an off-white solid (890 mg, 47percent). 1H NMR (500 MHz, CDCI3): delta 7.55-7.53 (m, 3H), 7.43 (d, 2H), 7.23 (d, 1 H), 7.12 (s, 1 H), 5.25 (s, 1 H), 3.94 (s, 3H), 2.54-2.51 (m, 4H), 2.1 1-2.13 (m, 1 H), 1.90-1.86 (m, 1 H), 1.34-1.25 (br s, 9H).
  • 2
  • [ 578007-66-6 ]
  • [ 1301610-33-2 ]
  • [ 1301610-57-0 ]
YieldReaction ConditionsOperation in experiment
87% With triethylamine;copper(l) iodide; bis(tri-t-butylphosphine)palladium(0); at 0 - 20℃; for 56.0h; Step 1: tert-Butyl (1-(4-((5-bromo-2-methoxypyridin-3- yl)ethynyl)phenyl)cyclobutyl)carbamate: To a degassed solution of 5-bromo-3-iodo-2- methoxypyridine (823 mg, 2.62 mmol) in triethylamine (8.0 mL) at 0 C was added Pd(PfBu3)2 (1 10.4 mg, 6 mol%), Cul (5.0 mg, 1 mol%) and terf-butyl (1-(4- ethynylphenyl)cyclobutyl)carbamate (71 1 mg, 2.62 mmol). The brown suspension was stirred for 56 hours at room temperature before the reaction mixture was suspended in dichloromethane and washed with brine, dried over magnesium sulphate, filtered and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (gradient 10 to 25% EtOAc in hexane) to give the title compound as a white solid (1.04 g, 87%). H-NMR (500 MHz, CDCI3) delta 8.14 (d, 1 H), 7.84 (d, 1 H), 7.52 (dd, 2H), 7.41 (d, 2H), 5.13 (bs, 1 H), 4.01 (s, 3H), 2.50-2.56 (m, 4H), 2.09-2.14 (m, 1 H), 1.84-1.90 (m, 1 H), 1.36 (bs, 9H).
 

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