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[ CAS No. 214360-73-3 ]

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Chemical Structure| 214360-73-3
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CAS No. :214360-73-3 MDL No. :MFCD02093721
Formula : C12H18BNO2 Boiling Point : 340°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :219.09 g/mol Pubchem ID :2734620
Synonyms :

Safety of [ 214360-73-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 214360-73-3 ]

  • Upstream synthesis route of [ 214360-73-3 ]
  • Downstream synthetic route of [ 214360-73-3 ]

[ 214360-73-3 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 109-04-6 ]
  • [ 214360-73-3 ]
  • [ 18471-73-3 ]
YieldReaction ConditionsOperation in experiment
79% With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 2 h; Step 4 [Show Image] 2-bromopyridine 5 (14.53 g, 92.0 mmol) and 4-aminophenylboronic acid pinacol ester (30.20 g, 138.0 mmol) were dissolved in dimethylformamide (200 ml). To the solution were added tetrakis triphenyl phosphine palladium (7.44 g, 6.4 mmol) and 2 M potassium carbonate solution (230 ml, 460 mmol) and the mixture was stirred for 2 hours at 100°C. The reactant was poured into water and filtered and the filtrate was extracted with ethyl acetate. The organic layer was washed with water and then saturated saline, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography. To the obtained solid were added ethyl acetate and hexane and the deposited solid was collected with filtration to give the desired substituted aniline 6 (12.35 g, yield 79 percent). 1H-NMR (DMSO-d6) δppm: 5.42 (s, 2H), 6.63 (m, 2H), 7.14 (m, 1H), 7,69-7.75 (m, 2H), 7.79 (m, 2H), 8.51 (m, 1H).
79% With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 2 h; 2-bromopyridine 5 (14.53 g, 92.0 mmol) and 4-aminophenylboronic acid pinacol ester (30.20 g, 138.0 mmol) were dissolved in dimethylformamide (200 ml). To the solution were added tetrakis triphenyl phosphine palladium (7.44 g, 6.4 mmol) and 2 M potassium carbonate solution (230 ml, 460 mmol) and the mixture was stirred for 2 hours at 100° C. The reactant was poured into water and filtered and the filtrate was extracted with ethyl acetate. The organic layer was washed with water and then saturated saline, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography. To the obtained solid were added ethyl acetate and hexane and the deposited solid was collected with filtration to give the desired substituted aniline 6 (12.35 g, yield 79percent).1H-NMR (DMSO-d6) δ ppm: 5.42 (s, 2H), 6.63 (m, 2H), 7.14 (m, 1H), 7.69-7.75 (m, 2H), 7.79 (m, 2H), 8.51 (m, 1H).
Reference: [1] Patent: EP2280000, 2011, A1, . Location in patent: Page/Page column 32
[2] Patent: US2011/28468, 2011, A1, . Location in patent: Page/Page column 20
[3] MedChemComm, 2017, vol. 8, # 1, p. 176 - 183
[4] Patent: WO2006/55951, 2006, A2, . Location in patent: Page/Page column 33
  • 2
  • [ 19524-06-2 ]
  • [ 214360-73-3 ]
  • [ 13296-04-3 ]
Reference: [1] Chemical Communications, 2007, # 45, p. 4752 - 4754
[2] Patent: WO2006/63113, 2006, A2, . Location in patent: Page/Page column 75
  • 3
  • [ 214360-73-3 ]
  • [ 23449-08-3 ]
Reference: [1] Patent: EP2808323, 2014, A1,
[2] Patent: CN108440430, 2018, A,
  • 4
  • [ 4530-20-5 ]
  • [ 200731-31-3 ]
  • [ 214360-73-3 ]
  • [ 39968-33-7 ]
  • [ 880545-43-7 ]
Reference: [1] Patent: WO2008/32086, 2008, A1, . Location in patent: Page/Page column 120-121
[2] Patent: WO2008/32086, 2008, A1, . Location in patent: Page/Page column 120-121
  • 5
  • [ 619-58-9 ]
  • [ 214360-73-3 ]
  • [ 5730-78-9 ]
Reference: [1] Patent: US2003/153556, 2003, A1,
  • 6
  • [ 106-37-6 ]
  • [ 214360-73-3 ]
  • [ 3365-85-3 ]
YieldReaction ConditionsOperation in experiment
52% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 24 h; Schlenk technique; Inert atmosphere; Heating 1,4-dibromobenzene (0.980 g, 4.15 rnmol), SI (2.0 g, 9.13 mmol), Pd(PPh3)4 (0.3 g, 0.415 mmol), K2C03 (8.6 g, 62.3 mmol), water (10 mL), toluene (10 mL) were loaded in a 50 mL Schlenk flask loaded with a magnetic stirrer. The mixture was flash frozen in liquid N2, evacuated to an internal pressure of 50 mtorr, and allowed to thaw under static vacuum. The freeze/pump/thaw procedure was repeated three more times, after which the flask was backfilled with N2(g) and under N2 flow a water cooled condenser was attached with a red septum, bubbler and a positive N2(g) flow at the top. The reaction mixture was heated to 120 °C for 24 h under N2(g), tracked by TLC. The reaction mixture was cooled to room temperature, quenched with water (5 mL), extracted with EtOAc (3 x 10 mL) and the combined organic extracts were rinsed with water (3 x 10 mL), brine (3 x 10 mL), dried over anhydrous Na2S04(i) and filtered through celite. Removal of the solvent at 40 °C under reduced pressure in a rotary evaporator followed by column chromatography (S1O2, 45percent EtOAc in hexanes) afforded a white solid. Yield: 0.560 g (52percent). NMR (400 MHz, DMSO-ifc) δ 7.53 (s, 1H), 7.39 - 7.35 (d, 1H), 6.66 - 6.62 (d, 1H), 5.20 (s, 1H). 13C NMR (100 MHz, DMSO) δ 148.18, 137.93, 127.11, 126.82, 125.55, 114.22, 99.51, 39.52. HRMS (ESI-TOF) m/z calculated for Ci8Hi6N2 [M+H]+: 261.1393, found 261.1355.
Reference: [1] Patent: WO2018/13682, 2018, A1, . Location in patent: Page/Page column 27
[2] Chemical Communications, 2018, vol. 54, # 50, p. 6947 - 6950
  • 7
  • [ 128143-89-5 ]
  • [ 214360-73-3 ]
  • [ 178265-65-1 ]
Reference: [1] Dalton Transactions, 2017, vol. 46, # 22, p. 7309 - 7316
[2] Organic and Biomolecular Chemistry, 2014, vol. 12, # 44, p. 8836 - 8839
  • 8
  • [ 626-39-1 ]
  • [ 214360-73-3 ]
  • [ 118727-34-7 ]
Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 35, p. 11310 - 11315[2] Angew. Chem., 2018, vol. 130, p. 11480 - 11485,6
  • 9
  • [ 75-36-5 ]
  • [ 214360-73-3 ]
  • [ 214360-60-8 ]
Reference: [1] Patent: WO2006/51851, 2006, A1, . Location in patent: Page/Page column 73
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 10, p. 4790 - 4799
[3] Angewandte Chemie - International Edition, 2017, vol. 56, # 43, p. 13351 - 13355[4] Angew. Chem., 2017, vol. 129, p. 13536 - 13540,5
  • 10
  • [ 108-24-7 ]
  • [ 214360-73-3 ]
  • [ 214360-60-8 ]
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 33, p. 4780 - 4783
[2] Journal of the American Chemical Society, 2005, vol. 127, # 38, p. 13094 - 13095
  • 11
  • [ 24424-99-5 ]
  • [ 214360-73-3 ]
  • [ 330793-01-6 ]
Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 11, p. 3069 - 3076
  • 12
  • [ 214360-73-3 ]
  • [ 796967-16-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 7, p. 1584 - 1597
  • 13
  • [ 214360-73-3 ]
  • [ 796967-16-3 ]
Reference: [1] Chemical Communications, 2015, vol. 51, # 29, p. 6384 - 6387
  • 14
  • [ 214360-73-3 ]
  • [ 170011-57-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 22, p. 7860 - 7883
  • 15
  • [ 214360-73-3 ]
  • [ 929203-04-3 ]
Reference: [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 44, p. 11581 - 11584[2] Angew. Chem., 2013, vol. 125, # 44, p. 11795 - 11798
[3] Journal of Organic Chemistry, 2014, vol. 79, # 5, p. 1979 - 1988
  • 16
  • [ 7597-22-0 ]
  • [ 214360-73-3 ]
  • [ 1197159-91-3 ]
YieldReaction ConditionsOperation in experiment
88% With sodium carbonate In 1,2-dimethoxyethane; water for 5 h; Reflux The mixture of 2-chloro-4,6-dimorpholin-4-yl-[1,3,5]triazine (2, 30 g, 0.105 mol) 4-aminophenylboronic acid pinacol ester (3, 25.7 g, 0.117 mol, Boron Molecular), sodium carbonate (23 g , 0.21 mol) and tetrakistriphenylphosphine palladium (1 g, O.δwt percent Aldrich) in water (150 ml) and dimethoxyethane (DME, 450 ml) was heated at reflux for 5 hours. The reaction mix was cooled to the room temperature and filtered through paper filter. The layers of the filtrate were separated, the organic layer was washed with brine and concentrated. The residue was dissolved in methylene chloride, washed with brine, dried over sodium sulfate and concentrated. The solids were triturated with diethyl ether, filtered, and air dried to give the beige solids (31.5 g, 0.092 mol). Yield 88percent; Mass: 343.1 (M+H)+.
83% With sodium carbonate In 1,2-dimethoxyethane; water for 24 h; Reflux A mixture of 2-chloro-4,6-di-morpholin-4-yl-[1,3,5]triazine (1.4 g, 4.9 mmoles), a catalytic amount of tetrakis(triphenylphosphine)palladium(0) (70 mg, 0.061 mmoles), sodium carbonate solution 2 M (3 mL), 4-aminophenylboronic acid pinacol ester (1.6 g, 7.3 mmoles) and DME (100 mL) was refluxed for 24 hours.
The solvent was evaporated, and the residue was dissolved in methylene chloride and filtered through Celite.(TM)..
The filtrate was washed with water (200 mL) and the organic layer was dried with magnesium sulfate.
This was filtered and the solvent was evaporated.
The residue was purified by Silica gel column chromatography and eluted with Ethyl acetate/hexanes (1:1) to give 1.40 g, (83percent yield) of 4-(4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl)aniline as an amorphous solid. (M+H) 343.
83% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane for 24 h; Reflux A mixture of 2-chloro-4,6-di-morpholin-4-yl-[1,3,5]triazine (1.4 g, 4.9 mmoles), a catalytic amount of tetrakis(triphenylphosphine)palladium(0) (70 mg, 0.061 mmoles), sodium carbonate solution 2 M (3 mL), 4-aminophenylboronic acid pinacol ester (1.6 g, 7.3 mmoles) and DME (100 mL) was refluxed for 24 hours. The solvent was evaporated, and the residue was dissolved in methylene chloride and filtered through Celite™. The filtrate was washed with water (200 mL) and the organic layer was dried with magnesium sulfate. This was filtered and the solvent was evaporated. The residue was purified by Silica gel column chromatography and eluted with Ethyl acetate/hexanes (1:1) to give 1.40 g, (83percent yield) of 4-(4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl)aniline as an amorphous solid. (M+H) 343.
73.5% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane for 24 h; Reflux; Inert atmosphere Synthetic method: 4,4'-(6-chloro-1,3,5-triazine-2,4-diyl)bismorpholine (3.0 g, 10.52 mmol) was dissolved in DME (30 mL) and added sequentially. Pd(PPh3)4 (0.12g, 0.10mmol), 2.0M Na2CO3 solution (6.40mL) and 4-aminoPhenylboronic acid pinacol ester (3.46 g, 15.78 mmol) was refluxed for 24 h under N2. Evaporate the solvent under reduced pressure and dissolve the residueIn CH 2 Cl 2 (50 mL), it was washed twice with water (50 mL×2), once with saturated NaCl (30 mL), and dried over anhydrous Na 2 SO 4 . Steaming under reduced pressureThe solvent and the residue were separated by column chromatography, eluent: EA/PE = 1/1 to give the desired product 2.65 g, yield: 73.50percent.
52% With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 110℃; for 24 h; Inert atmosphere General procedure: A mixture of compound 7a (5 mmol), 4-aminophenylboronic acid pinacol ester (10 mmol), Pd(Ph3P)4 (0.1 mmol), Na2CO3 (10 mmol) in 1,4-dioxane/H2O (20 mL) was stirred at 110 °C for 24 h under Ar.
The reaction mixture was filtered through celite. The filtrate was concentrated in vacuo and then extracted with EtOAc.
The organic layer was evaporated to give a residue, which was purified by chromatography (petroleum ether/EtOAc, 5:1) to give pure product as a yellow solid, yield 59percent.

Reference: [1] Patent: WO2010/96619, 2010, A1, . Location in patent: Page/Page column 27-28
[2] Patent: US2009/291079, 2009, A1, . Location in patent: Page/Page column 37
[3] Journal of Medicinal Chemistry, 2010, vol. 53, # 6, p. 2636 - 2645
[4] Patent: US2017/119778, 2017, A1, . Location in patent: Paragraph 0929
[5] Patent: CN108191837, 2018, A, . Location in patent: Paragraph 0179; 0180
[6] European Journal of Medicinal Chemistry, 2017, vol. 141, p. 721 - 733
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