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Chemical Structure| 380893-73-2 Chemical Structure| 380893-73-2

Structure of 380893-73-2

Chemical Structure| 380893-73-2

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Product Details of [ 380893-73-2 ]

CAS No. :380893-73-2
Formula : C10H15BrNO3P
M.W : 308.11
SMILES Code : BrC1=CN=C(CP(OCC)(OCC)=O)C=C1
MDL No. :MFCD08704782

Safety of [ 380893-73-2 ]

Application In Synthesis of [ 380893-73-2 ]

* 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 [ 380893-73-2 ]

[ 380893-73-2 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 380893-73-2 ]
  • [ 768-35-4 ]
  • [ 380894-77-9 ]
YieldReaction ConditionsOperation in experiment
75% With sodium carbonate;5%-palladium/activated carbon; In 2-methylpropyl acetate; water; at 70 - 80℃; for 3h; Example 1; Preparation of [5-(3-Fluoro-phenyl)-pyridin-2-ylmethyl]-phosphonic acid diethyl ester; To a reaction vessel was charged (100 g, 0.29 mol) of phosphonate compound 139 (where R9 is ethyl- for all occurrences), 5% Pd/C 50% wet (5.0 g), 3-fluorophenylboronic acid (61 g; 0.44 mol) and sodium carbonate (100 g; 0.94 mol). 600 ml of iso-butyl acetate was charged and the mixture agitated. 400 ml of water was charged, and the agitated mixture was heated to 70-80 C. for at least 3 h at which time an HPLC assay indicated complete reaction. Upon completion, the reaction mixture was cooled to 25 C. and filtered to remove the Pd/C catalyst. The catalyst cake was washed with 200 ml iso-butyl acetate (combined with the filtrate/batch) and 100 ml water (waste). 25% sodium hydroxide solution was used to adjust batch to pH 11-13. During the process the reaction mixture was maintained at a temperature of from 20 C. to 30 C. The organic layer was separated and washed with 500 ml water with agitation. A 25% sodium hydroxide solution was used to adjust the pH of the batch to a pH value of from pH 11 to pH13. Throughout the was the temperature was maintained at a value of from about 20 C. to about 30 C. After washing the layers were separated and the organic layer was washed with 300 ml of 2% sodium chloride solution with 10-15 minutes with agitation. The layers were separated and an HPLC assay of the organic layer indicated impurities were reduced to a desirable level. Darco (10 g) was added to the organic layer. The resultant slurry was agitated for 1 hour, and then filtered to remove the de-coloring agent. The filter cake was washed with 200 ml iso-butyl acetate (combined with the filtrate/batch) and the batch was concentrated under reduced pressure to about 200 ml at from 40 C. to 50 C., then cooled to a temperature of from 15 C. to 25 C. Heptanes (1000 ml) were charged into the cold concentrate over 2.5-3 hr, maintaining the temperature at from about 15 C. to 25 C. The mixture was cooled to a temperature of from -15 C. to -5 C. over 3 hr and agitated at the same temperature for 1 hr. The crystalline solid was filtered, washed with 200 ml heptanes, and dried overnight under vacuum at a temperature of from about 25 C. to 35 C. to provide 70.37 g (75%). Mp 61-63 C. 1H NMR (CDCl3) delta 1.3 (t, J=7.05 Hz, 6H), 3.47 (d, J=22.02 Hz, 2H), 4.12 (q, J=7.08 Hz, 4H), 7.10 (ddd, J=8.42, 2.55, 0.88, Hz, 1H), 7.28 (ddd, J=9.85, 2.36, 1.80 Hz, 1 H), 7.36 (dt, J=7.86, 1.27, Hz, 1H), 7.46 (m, 1H), 7.83 (ddd, J=8.1, 2.2, 0.32 Hz, 1H), 8.76 (d, J=2.38, 1H).
  • 2
  • [ 380893-73-2 ]
  • [ 214360-47-1 ]
  • [ 869898-68-0 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 100℃; for 4.0h; A solution of 18 (2.12 g, 6.88 mmol), Pd(PPh3)4 (400 mg, 0.346 mmol, 5 mol %), <strong>[214360-47-1](2-cyanophenyl)boronic acid 2,2-dimethylpropanediol-1,3-cyclic ester</strong> (1.8 g, 8.37 mmol, 1.2 eq.) and K2CO3 (3.0 g, 27.49 mmol, 4 eq.) in toluene(20 ml)-EtOH(10 ml)-H2O(5 ml) mixture was heated in a sealed tube at 100 C. for 4 hr. The mixture was diluted with 150 ml H2O and extracted with 3×50 ml EtOAc. The combined organic layer was washed with brine, dried over MgSO4, filtered, concentrated and purified by chromatography to provide 23 (1.82 g) as a solid. 1H NMR (400 MHz, CDCl3) 8.66 (d, J=2.0, 1H), 7.86 (dd, J=8.0, 2.0, 1H), 7.78-7.75 (m, 1H), 7.68-7.64 (m, 1H), 7.50-7.45 (m, 3H), 4.08 (dq, J=8.0, 7.2, 4H), 3.46 (d, J=22, 2H), 1.26 (t, 6H).
  • 3
  • [ 380893-73-2 ]
  • 3-fluorophenylboronic acid [ No CAS ]
  • [ 380894-77-9 ]
YieldReaction ConditionsOperation in experiment
75% With sodium carbonate;5%-palladium/activated carbon; In water; toluene; at 75℃; for 5h; To a reaction vessel was charged sodium carbonate (8 g; 75.5 mmol), 30 ml of water and stirred until dissolved. To this solution were added 3-fluorophenylboronic acid (6 g; 42.9 mmol) and 5% Pd/ C 50% wet (0.5 g). The toluene solution of Compound 38 from above was then added and the mixture was heated to 75 0C for at least 5 h at which time an HPLC assay indicated complete reaction. Upon completion, the reaction mixture was cooled to 25 C and filtered to remove the Pd/ C catalyst. The layers were separated and the organic layer was washed and concentrated under reduced pressure to about 20ml. Heptane (20 EPO <DP n="50"/>ml) was slowly added, seed ciystals were added, and the mixture was cooled to -10 0C over 2 h. The crystalline solid was filtered, washed with heptane and dried overnight under vacuum at 30 0C to provide 8 g (75%). Mp 61 - 63 C. 5 1.3 (t, J = 7.08 Hz, 3H), 3.42 (s, IH), 3.49 (s, IH), 4.1 (q, J = 7.08 Hz, 2H), 7.04 - 7.11 (m, IH), 7.23 - 7.3 (m, IH), 7.32 - 7.3 (m, IH), 7.32 -7.36 (m, IH), 7.39 -7.48 (m, IH), 7.81 (ddd, J = 8.08, 2.3, 0.41 Hz, IH), 8.74 (d, J = 2.36, IH).
 

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