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Chemical Structure| 1112983-11-5 Chemical Structure| 1112983-11-5

Structure of 1112983-11-5

Chemical Structure| 1112983-11-5

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Product Details of [ 1112983-11-5 ]

CAS No. :1112983-11-5
Formula : C7H5BrN2O
M.W : 213.03
SMILES Code : N#CCOC1=CC(Br)=CN=C1
MDL No. :MFCD18254216

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Application In Synthesis of [ 1112983-11-5 ]

* 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 [ 1112983-11-5 ]

[ 1112983-11-5 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 1112983-11-5 ]
  • [ 885069-14-7 ]
  • [ 1112982-08-7 ]
YieldReaction ConditionsOperation in experiment
7.3% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; Example 288; N-(6-(5-(Cyanomethoxy)pyridin-3-yl)benzo[d]thiazol-2-yl)acetamide; A dry 15 mL, one neck round bottom flask was charged with 2-(5-bromopyridin-3-yloxy)acetonitrile (0.162 g, 0.762 mmol), N-(6-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)acetamide (.2021 g, 0.635 mmol), 5 mL THF and a stirbar. The flask was flushed with Ar for 2 minutes, and fitted with an inert atmosphere inlet. To the stirring solution was added tetrakis(triphenylphosphine)palladium (0.147 g, 0.127 mmol) followed by 2 M sodium carbonate (0.953 ml, 1.91 mmol). The slurry was refluxed overnight, and cooled to room temperature. The mixture was poured onto 15 mL water and extracted with DCM (3 x 20 mL). The DCM extracts were Loaded onto an unbuffered Varian Chem elute CE1010 (100 mL, PN 12198010). The tube was extracted with DCM (4 x 20 mL). The combined <n="126"/>extracts were concentrated in vacuo, and the residue was taken up in 1 mL DCM. A precipitate formed, which was collected using a course glass filter fitted with a 0.22 mum syringe filter. The solid was dried at 60 C at < 1 mmHg for 1 h to afford N-(6-(5-(Cyanomethoxy)pyridin-3-yl)benzo[d]thiazol-2- yl)acetamide (15 mg, 7.3%). 1H NMR (300 MHz, Pyr) delta ppm 2.36 (s, 3 H) 4.98 (br. s., 1 H) 5.56 (s, 2 H) 7.75 (dd, J=8.40, 1.90 Hz, 1 H) 7.93 (dd, 7=2.81 , 1.86 Hz, 1 H) 8.02 (dd, J=8.44, 0.48 Hz, 1 H) 8.27 (dd, J=I .90, 0.44 Hz, 1 H) 8.77 (d, 7=2.85 Hz, 1 H) 8.93 (d, 7=1.83 Hz, 1 H). 13C NMR (75 MHz, Pyr) delta ppm 23.71 (s, 1 C) 55.20 (s, 1 C) 116.92 (s, 1 C) 120.84 (s, 1 C) 121.15 (s, 1 C) 122.27 (s, 1 C) 126.25 (s, 1 C) 133.18 (s, 1 C) 134.41 (s, 1 C) 137.61 (s, 1 C) 138.12 (s, 1 C) 143.50 (s, 1 C) 150.53 (s, 1 C) 154.29 (s, 1 C) 160.70 (s, 1 C) 170.19 (s, 1 C). HPLC-MS: retention time =1.34 min (93.6%(at)215 nm; 96.7% (at)254 nm; m/z = 325.6, calculated for C6H12N2O4S + H+ = 325.1).
 

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