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[ CAS No. 286961-14-6 ]

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Chemical Structure| 286961-14-6
Chemical Structure| 286961-14-6
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Product Details of [ 286961-14-6 ]

CAS No. :286961-14-6 MDL No. :MFCD03840345
Formula : C16H28BNO4 Boiling Point : 348°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :309.21 g/mol Pubchem ID :4642098
Synonyms :

Safety of [ 286961-14-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
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Application In Synthesis of [ 286961-14-6 ]

  • Downstream synthetic route of [ 286961-14-6 ]

[ 286961-14-6 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 166281-37-4 ]
  • [ 286961-14-6 ]
  • [ 947614-68-8 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide at 85℃; for 24.5h; 22.22a 2-Bromo-4,5-difluorophenol (2857 µl), N-Boc-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester (7.73 g), potassium carbonate (10.36 g) and dichloro(1,1'-bis(diphenyl-phosphino)-ferrocene)palladium(II) DCM adduct (1.22 g) were dissolved in DMF (150 ml) in a dry apparatus under argon and the mixture was degassed by bubbling with argon for 30 min. The orange suspension was then heated under argon in an oil bath at 85 °C for 1 day to give a dark purple suspension. The reaction mixture was filtered through Celite and evaporated to dryness in vacuo. The crude product was purified by flash chromatography to yield pale green crystals.
Stage #1: 2-bromo-4,5-difluorophenol With triethylsilyl chloride; triethylamine In dichloromethane at 20℃; Stage #2: tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride In N,N-dimethyl-formamide at 110℃;
With potassium carbonate In N,N-dimethyl-formamide at 85℃; for 24h; 8.a 2-Bromo-4,5-difluorophenol (2857 µl), N-Boc-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester (7.73 g), potassium carbonate (10.36 g) and dichloro(1,1'-bis(diphenylphosphino)-ferrocene)palladium(II) DCM adduct (1.22 g) were dissolved in DMF (150 ml) in a dry apparatus under argon and the mixture was degassed by bubbling with argon for 30 min. The orange suspension was then heated under argon in an oil bath at 85°C for 1 d to give a dark purple suspension. The reaction mixture was filtered through Celite and evaporated to dryness in vacuo. The crude product was purified by flash chromatography to yield pale green crystals.
  • 2
  • [ 1211536-93-4 ]
  • [ 286961-14-6 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
23% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In 1,4-dioxane; water at 110℃; for 4h; Inert atmosphere; The synthesis of tert-butyl 4-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-6-yl)-5,6- dihydropyridine-1(2H)-carboxylate To a solution of aryl bromide (233 mg, 1.0 mmol) in 1,4- dioxane (8 mL) and H2O (2 mL) was added tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl)-5,6-dihyropyridine-1(2H)-carboxylate (Eunkyung, K. et al Bioorganic & Medicinal Chemistry Letters 2008, 18, 4993-4996) (245 mg, 0.8 mmol), Pd(dppf)Cl2.DCM (41 mg, 0.05 mmol) and K2CO3(276 mg, 2.0 mmol) under N2. The mixture was stirred at 110 °C for 4 h, cooled to rt, diluted with H2O (80 mL) and extracted with EtOAc (60 mL x 3 . The organic layers separated, dried (Na2SO4) concentrated in vacuo to afford a residue which was purified by column chromatography (petroleum ether/EtOAc = 5:1 to 2:1) to give the title compound (77 mg, yield 23%) as yellow solid ESI-MS (M+H)+: 335.2.1H NMR (400 MHz, CDCl3) : 10.82 (br, 1H), 8.71 (s, 1H), 6.73 (s, 1H), 6.68-6.56 (m, 1H), 4.16-4.13 (m, 2H), 3.70-3.65 (m, 2H), 2.62-2.60 (m, 2H), 1.46 (s, 9H).
  • 3
  • [ 1256584-75-4 ]
  • [ 286961-14-6 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
71% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 110℃; for 1.5h; Inert atmosphere; Microwave irradiation; 23 Synthesis of 2-(2-(3-(1-acetyl-1,2,3,6-tetrahydropyridin-4-yl)-4-ethylphenyl) propan-2-yl)-1H-indole-6-carbonitrile (25) A mixture of 23 (350 mg, 0.68 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (422 mg, 1.36 mmol), Pd(PPh3)4 (158 mg, 0.136 mmol), and Na2CO3 (2 M in water, 1.5 mL) in dioxane (4.5 mL) was degassed with nitrogen for 5 min and then heated at 110 °C under microwave for 1.5 h. After the completion of the reaction, the mixture was diluted with EtOAc (20 mL) and filtered. The filtrate was concentrated and purified by chromatograph (petroleum/acetoacetate) to afford a yellow solid (275 mg, 71% yield): 1H NMR (300 MHz, CDCl3) δ 9.12 (s, 1H), 8.11 (d, J = 8.4 Hz, 1H), 7.69 (s, 1H), 7.41 (dd, J = 8.4, 1.2 Hz, 1H), 7.16-7.07 (m, 2H), 6.98-6.91 (m, 1H), 5.52-5.45 (m, 1H), 4.04-3.94 (m, 2H), 3.59 (t, J = 5.5 Hz, 2H), 2.57 (q, J = 7.5 Hz, 2H), 2.36-2.24 (m, 2H), 1.91 (s, 6H), 1.48 (s, 9H), 1.37 (s, 9H), 1.16 (t, J = 7.5 Hz, 3H). The obtained solid was dissolved in toluene/TFA (5 mL/5 mL). The mixture was heated at 80 °C for 3 h under nitrogen atmosphere. After being cooled to room temperature, the reaction mixture was evaporated in vacuum, and basified with saturated sodium bicarbonate until pH > 7. After extraction with EtOAc, the combined mixture was washed with brine, dried over sodium sulfate, and evaporated. The residue was purified by chromatograph (CHCl3/MeOH) to give the corresponding intermediate as a pale yellow solid (80 mg, 45%): 1H NMR (300 MHz, CDCl3 + CD3OD) δ 7.60-7.48 (m, 2H), 7.21 (d, J = 8.3 Hz, 1H), 7.10-6.99 (m, 2H), 6.94 (s, 1H), 6.42 (s, 1H), 5.53-5.43 (m, 1H), 3.40-3.30 (m, 2H), 2.96 (t, J = 5.6 Hz, 2H), 2.53 (q, J = 7.5 Hz, 2H), 2.21-2.10 (m, 2H), 1.70 (s, 6H), 1.11 (t, J = 7.5 Hz, 3H). The intermediate (80 mg, 0.22 mmol) was dissolved in 2 mL of pyridine. Ac2O (0.24 mL, 2.6 mmol) and DMAP (3 mg, 0.025 mmol) were added. The solution was stirred at room temperature overnight until the completion of the reaction. After removal of the solventunder vacuum, DCM (80 mL) was added and the solution was washed with diluted hydrochloric acid (1 N) followed by brine, dried over sodium sulfate, and then ltered. After evaporation of the solvent, the residue was puried by chromatograph (CHCl3/ MeOH) to yield the title product 25 as a white solid (81 mg, 91%yield) (29% overall yield in three steps): 1H NMR (300 MHz, CDCl3)d 8.51 (s, 1H), 7.60 (d, J 8.1Hz, 1H), 7.55 (s, 1H), 7.33e7.27 (m, 1H),7.18e7.05 (m, 2H), 6.97 (s, 1H), 6.51 (s, 1H), 5.60e5.43 (m, 1H),4.20e4.12 (m, 1H), 4.11e4.00 (m, 1H), 3.82-3.72 (m, 1H), 3.66-3.58 (m, 1H), 2.56 (q, J 7.5 Hz, 2H), 2.41-2.26 (m, 2H), 2.17-2.07 (m,3H), 1.76 (s, 6H), 1.17 (t, J 7.5 Hz, 3H). 13C NMR (126 MHz, CDCl3)d 169.6 and 169.4 (1C), 152.0, 144.4, 141.9, 139.6 and 139.5 (1C),138.8, 136.7, 134.9, 131.7, 128.7, 126.0 and 125.9 (1C), 125.5, 123.0 and 122.8 (1C), 121.3, 120.8, 115.2, 103.4, 99.7, 45.5 and 43.5 (1C),41.8 and 38.4 (1C), 39.7, 31.2 and 30.5 (1C), 29.7, 25.6, 22.0 and 21.6 (1C), 15.7. MS (EI) 411 (M). HRMS: calcd for C27H29N3O (M),411.2311; found 411.2313.
  • 4
  • [ 1211520-71-6 ]
  • [ 286961-14-6 ]
  • [ 1621519-76-3 ]
YieldReaction ConditionsOperation in experiment
42% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 100℃; Inert atmosphere; Step 5:
tert-butyl 4-(5-bromo-4-methoxypyridin-2-yl)-5,6-dihydropyridin-1(2H)-carboxylate Step 5: tert-butyl 4-(5-bromo-4-methoxypyridin-2-yl)-5,6-dihydropyridin-1(2H)-carboxylate Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridin-1(2H)-carboxylate (3.09g, 10 mol), 2,5-dibromo-4-methoxypyridine (2.67 g, 10 mmol), Pd(PPh3)4 (578 mg, 0.5 mmol), and K2CO3 (3.34 g, 24 mmol) were added to 1,4-dioxane (50 mL) and water (10 mL) and purged with nitrogen. The resultant was stirred at 100°C overnight. After the resultant was cooled, it was purified by silica gel column chromatography to give tert-butyl 4-(5-bromo-4-methoxypyridin-2-yl)-5,6-dihydropyridin-1(2H)-carboxylate (1.55 g, 42% yield). MS m/z [ESI]: 369.1 [M+1]. 1H-NMR (400 MHz, CDCl3):δ= 8.49(s, 1H), 7.26 (s, 1H), 6.58 (s, 1H), 4.13 (t, 2H), 3.97 (s, 3H), 2.62 (d, 2H), 1.49 (s, 9H).
  • 5
  • [ 286961-14-6 ]
  • [ 1380575-45-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; potassium phosphate tribasic trihydrate; palladium diacetate / tetrahydrofuran / 85 °C / Inert atmosphere 2: 50% palladium on charcoal; hydrogen / methanol / 45 °C 3: hydrogenchloride / water / 2 h / 55 °C
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