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Chemical Structure| 916889-45-7 Chemical Structure| 916889-45-7

Structure of 916889-45-7

Chemical Structure| 916889-45-7

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Product Details of [ 916889-45-7 ]

CAS No. :916889-45-7
Formula : C5H5BrN2O3
M.W : 221.01
SMILES Code : O=C(C1=NN=C(Br)O1)OCC
MDL No. :MFCD22415767
InChI Key :PHHNZUKINCAFBC-UHFFFAOYSA-N
Pubchem ID :68452326

Safety of [ 916889-45-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 916889-45-7 ]

* 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 [ 916889-45-7 ]

[ 916889-45-7 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 4970-53-0 ]
  • [ 916889-45-7 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 19; 5-[(S)-3-(2-Bromo-5-fluoro-phenoxy)-pyrrolidin-l-yll-ri,3,41oxadiazole-2-carboxamide; Step 1 : Ethyl 5-bromo-l ,3,4-oxadiazole-2-carboxylate; To a suspension of ethyl 5-amino-l,3,4-oxadiazole-2-carboxylate (8.8 g, 56 mmol) in CH3CN (187 mL) was added CuBr2 (18.8g, 84 mmol). The mixture turned dark green <n="49"/>and further stirred for 15 min at room temperature. t-BuONO, 90% (15 mL, 112 mmol) was added and stirred at room temperature for 2h then heated at 50 0C for 0.5h. The solvent was then evaporated in vacuo. Water (100 mL) and EtOAc (100 mL) were added and the mixture was filtered through celite and washed with EtOAc. The EtOAc layer was separated, and the aqueous layer extracted with EtOAc (2 x 50 mL). The combined organic layers were dried over Na2SO4 and concentrated. The product was recrystallized from CH2Cl2/hexanes to give the title compound as solid. 1H NMR (400 MHz, CDCl3): delta 4.56 (q, 2H), 1.51 (t, 3H).
  • 2
  • [ 916889-45-7 ]
  • [ 960492-20-0 ]
  • ethyl-5-[(3S)-3-(2-bromo-5-fluorophenoxy)pyrrolidin-1-yl]-1,3,4-oxadiazole-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 20℃; for 0.5h; Step 2: Ethyl-5-r(3S)-3-(2-bromo-5-fluorophenoxy)pwolidin-l-yl1-l,3,4-oxadiazole-2- carboxylate; To a mixture of ethyl 5-bromo-l,3,4-oxadiazole-2-carboxylate (0.5 g, 2.26 mmol) and (31S)-3-(2-bromo-5-fluorophenoxy)pyrrolidine (0.5 mL, 3.4 mmol) in THF (4.5 mL) was added DBU (0.5 mL, 3.4 mmol). The mixture was stirred at room temperature for 0.5 h then filtered and the filtrate concentrated. Purification by Combifiash (SiO2, gradient elution 70-100 % EtOAc/Hexanes) afforded the desired product as solid. lH NMR (500 MHz, acetone-^*): delta 7.62 (dd, IH), 7.15 (d, IH), 6.79 (td, IH), 5.46-5.40 (m, IH), 4.43 (q, 2H), 4.08 (dd, IH), 3.92-3.80 (m, 3H), 2.52-2.40 (m, 2H), 1.38 (t, 3H). MS: m/z 400, 402 (MH+).
  • 3
  • [ 916889-45-7 ]
  • 6-chlorooxazolo[4,5-b]pyridin-2-amine [ No CAS ]
  • ethyl 5-((6-chlorooxazolo[4,5-b]pyridin-2-yl)amino)-1,3,4-oxadiazole-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
6% With caesium carbonate; In N,N-dimethyl-formamide; at 20℃; for 16h; To a solution of 6-chlorooxazolo[4,5-b]pyridin-2-amine (500 mg, 2.95mmol) in DMF (5.0 mL) were added <strong>[916889-45-7]ethyl 5-bromo-1,3,4-oxadiazole-2-carboxylate</strong> (980mg, 4.43mmol) and 052003 (2.88g,8.87mmol) at rt. The rection mixture was stirred at rt for 16h. TLC showed the reaction to be complete. The reaction mixture was diluted with H20 (50mL) and extracted with EtOAc (3x50mL). The organics were dried (Na2504), filtered and concentrated under reduced pressure. The crude residue was purified by prep HPLC to afford 6-chlorooxazolo[4,5-b]pyridin-2-amineas an off white solid. Yield: 54mg (6 %); MS (ESl+) for CHNOS m/z 310.22 [M+H] LC purity 99.4 % (Ret. Time- 3.73mm); 1H NMR (400 MHz, DMSO-d6): 8.25 (5, 1H), 8.12 (5, 1H), 4.38 (q, J= 7.0 Hz, 2H), 1.33 (t, J= 7.0 Hz, 3H).
 

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