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[ CAS No. 888721-86-6 ]

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Chemical Structure| 888721-86-6
Chemical Structure| 888721-86-6
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Product Details of [ 888721-86-6 ]

CAS No. :888721-86-6 MDL No. :MFCD11054039
Formula : C15H23BN2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :290.17 g/mol Pubchem ID :-
Synonyms :

Safety of [ 888721-86-6 ]

Signal Word:Warning Class:
Precautionary Statements:P280-P305+P351+P338 UN#:
Hazard Statements:H302 Packing Group:
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Application In Synthesis of [ 888721-86-6 ]

  • Downstream synthetic route of [ 888721-86-6 ]

[ 888721-86-6 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 186593-43-1 ]
  • [ 888721-86-6 ]
  • 2-methyl-2'-morpholino-[3,4'-bipyridin]-5-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,2-dimethoxyethane; at 110℃; for 0.25h;Microwave irradiation; Synthesis of 2-methyl-2'-morpholino-[3,4'-bipyridin]-5-amine To a solution of <strong>[186593-43-1]5-bromo-6-methylpyridin-3-amine</strong> (1.0 equiv.) and 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)morpholine (1.7 equiv.) in DME and 2M sodium carbonate (4:1, 0.14 M) was added PdCl2(dppf)-DCM adduct (0.1 equiv.) in a microwave vial equipped with a stir bar. The reaction was heated to 110 C. for 15 min in the microwave. The cooled reaction mixture was partitioned between water and ethyl acetate. The organic phase was dried with sodium sulfate, filtered and concentrated. The crude material was purified by flash chromatography over silica gel (DCM with a 0-20% methanol gradient). The pure fractions were concentrated in vacuo to afford 2-methyl-2'-morpholino-[3,4'-bipyridin]-5-amine in quantitative yield. LCMS (m/z) (M+H)=271.1, Rt=0.26 min.
  • 2
  • [ 1040377-12-5 ]
  • [ 73183-34-3 ]
  • [ 888721-86-6 ]
YieldReaction ConditionsOperation in experiment
56% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In N,N-dimethyl-formamide at 80℃; Inert atmosphere; 62 Synthesis of 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)morpholine Synthesis of 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)morpholine 4-(4-bromopyridin-2-yl)morpholine (1.10 equiv), bis(pinacolato)diboron (1.0 equiv.), potassium acetate (4.0 equiv), and PdCl2(dppf)CH2Cl2 (0.05 equiv.) were added to a rb flask which was purged with nitrogen. DMF (0.20 M) was added and the mixture was heated to 80° C. overnight. The reaction was cooled to rt, quenched with water, and the product was extracted into EtOAc (3*). The combined organics were dried over Na2SO4, filtered, and concentrated. The crude was loaded onto silica gel and purified via ISCO to yield 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)morpholine as a light brown foam (56%). 1H NMR (400 MHz, ) δ ppm 1.33 (s, 12H) 3.49-3.55 (m, 4H) 3.79-3.83 (m, 4H) 6.98 (d, J=4.70 Hz, 1H) 7.03 (s, 1H) 8.21 (d, J=4.70 Hz, 1H).
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃; for 12h; Inert atmosphere; 7.2 Step 2. 4-(4-(4, 4, 5, 5-Tetramethyl-J 3, 2-dioxaborolan-2-yl)pyridin-2-yl )morpholine A mixture of 4-(4-bromo-2-pyridinyl)-morpholine (1.5 g, 6.17 mmol), (0516) bis(pinacolato)diboron (1.88 g, 7.40 mmol), KOAc (1.51 g, 15.43 mmol), and Pd(dppf)Cl2 (451 mg, 617.03 pmol) in dioxane (15 mL) was degassed and purged with N2 (3x); then the mixture was stirred at 80 °C for 12 h under N2 atmosphere. LC-MS showed 4-(4-bromo-2- pyridinyl)-morpholine was completely consumed and the desired mass was detected. The mixture was filtered and concentrated under reduced pressure to give the title compound (1.28 g, crude) as a black oil.
  • 3
  • [ 67400-25-3 ]
  • [ 888721-86-6 ]
  • 4-(4-(5-nitro-1H-indazol-3-yl)pyridin-2-yl)morpholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); potassium acetate; In ethanol; water; at 100℃; for 12h;Inert atmosphere; A mixture of 4-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridin-2- yl)morpholine (1.28 g, 6.15 mmol), 3-bromo-5-nitro-lH-indazole (1.79 g, 7.38 mmol), AcOK (1.81 g, 18.46 mmol), Pd(Amphos)Cl2 (436 mg, 615.32 pmol) in EtOH (20 mL) and H20 (5 mL) was degassed and purged with N2 (3x); then the mixture was stirred at 100 C for 12 h under N2 atmosphere. LC-MS showed desired mass was detected. The reaction mixture was concentrated under reduced pressure to remove solvent. To the reaction mixture was added HC1 (2N, 10 mL) to adjust to pH=4. EtOAc (40 mL) was added and the solid precipitated. The mixture was filtered and the cake was dried to give the title compound (l.2g, crude) as a gray solid.
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