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[ CAS No. 395652-44-5 ]

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2D
Chemical Structure| 395652-44-5
Chemical Structure| 395652-44-5
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Product Details of [ 395652-44-5 ]

CAS No. :395652-44-5MDL No. :MFCD18384524
Formula :C9H9NOBoiling Point :301.4±22.0°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :147.17Pubchem ID :11008063
Synonyms :

Computed Properties of [ 395652-44-5 ]

TPSA : 33.1 H-Bond Acceptor Count : 2
XLogP3 : 0.9 H-Bond Donor Count : 1
SP3 : 0.22 Rotatable Bond Count : 2

Safety of [ 395652-44-5 ]

Signal Word:WarningClassN/A
Precautionary Statements:P280-P305+P351+P338UN#:N/A
Hazard Statements:H302Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 395652-44-5 ]

  • Upstream synthesis route of [ 395652-44-5 ]
  • Downstream synthetic route of [ 395652-44-5 ]

[ 395652-44-5 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 5029-67-4 ]
  • [ 927-74-2 ]
  • [ 395652-44-5 ]
YieldReaction ConditionsOperation in experiment
67% With potassium phosphate In water; isopropyl alcohol at 80℃; for 20.00 h; Sealed tube General procedure: In a sealed tube, aryl iodide (1 mmol, 1 equiv.), K3PO4(2 mmol,2 equiv.), catalyst (2 molpercent Pd) were suspended in i-PrOH (3 mL)and H2O (3 mL). The acetylene derivative (1.2 mmol, 1.2 equiv.)was added and the resulting mixture was stirred at 80C for 20 h.After cooling to room temperature, EtOAc (20 mL) and H2O (20 mL)were added and the mixture was filtered over a pad of Celite®.The aqueous layer was extracted twice with EtOAc (2 × 20 mL). Thecollected organics extracts were washed by brine (60 mL), driedon MgSO4, filtered and concentrated under reduced pressure. Thecrude product was purified by flash chromatography.
Reference: [1] Applied Catalysis A: General, 2014, vol. 482, p. 157 - 162
  • 2
  • [ 109-04-6 ]
  • [ 927-74-2 ]
  • [ 395652-44-5 ]
YieldReaction ConditionsOperation in experiment
90% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In 1,4-dioxane at 20℃; Inert atmosphere Under nitrogen atmosphere, and at r.t., CuT (0.06 g, 0.31 mmol), dry Et3N (1.32 mL, 9.49 mmol) and bis-(triphenylphosphine)-palladium chloride (0.13 g, 0.18 mmol) were sequentially added to a solution of 2-bromopyridine (0.60 mL, 6.33 mmol) in 1,4-dioxane (10 mL). Then, but-3-yn-1-ol (0.57 mL, 7.59 mmol) was added dropwise at the same temperature.The resulting reaction mixture was left stirred overnight, then concentrated under reduced pressure, dissolved in EtOAc (80 mL) and washed with H20 (3 x 10 mL). The organic layer was dried over Na2504 and concentrated to dryness to give an oily crude (1.1 g). Purification by typical silica gel flash chromatography using a Teledyne ISCO apparatus (Cy/EtOAc from 90:10 to 30:70) afforded the pure title compound (0.84 g, 90percent), as a white solid. R= 1.25 mm. MS(ESI) m/z: 148 EM-H], 170 EM-Na], 186 EM-K]. ‘H NMR (DMSO-d6): ö 8.55—8.49 (m, 1H),7.76 (td, 1H, J= 7.8, 1.8 Hz), 7.44 (d, 1H, J= 7.8 Hz), 7.33 (ddd, 1H, J= 7.8, 4.9, 1.8 Hz), 4.92 (t, 1H, J= 5.2 Hz), 3.62-3.58 (m, 2H), 2.58 (t, 2H, J= 6.8 Hz).
77% at 0 - 70℃; Example 199 ;3 -Methoxy- N -methyl- N -( 4-(pyridin- 2-yl)but - 3 -ynyl)benzamide; 199(A) 4-(Pyridin-2-yl)but-3-yn-1-01; To a suspension of CuI (301 mg, 1.58 mmol) in TEA (40 mL) were added 2- bromopyridine (5 g, 31.6 mmol), followed by Pd2Cl2(PPh3)2 (1.11 g, 1.58 mmol) to give a yellow orange suspension. After cooling down to 0°C under N2, 3-butyn-l-ol (2.28 g, 31.6 mmol) was added. The resulting reaction mixture turned black and it was stirred overnight at 70°C. The reaction mixture was quenched at 0°C with water, TEA was removed under low pressure, and the organic layer was extracted 3x using DCM, washed with Ammonia, water, brine, dried over MgS04, filtered and concentrated. The crude residue was purified over silicagel chromatography (prepacked 250 g silicagel column, DCM/MeOH : from 99/1 to 95/5 as eluent) to afford 3.60 g of 4- (pyridin-2-yl)but-3-yn-1-ol as a brown oil (Yield : 77percent). LCMS (RT) : 1.58min; MS (ES+) gave m/z : 148 Rf (DCM/MeOH : 95/5) =0.23
Reference: [1] Tetrahedron Letters, 2005, vol. 46, # 10, p. 1717 - 1720
[2] Journal of Organic Chemistry, 2003, vol. 68, # 3, p. 762 - 769
[3] Patent: WO2014/144836, 2014, A2. Location in patent: Paragraph 0526; 0527
[4] European Journal of Organic Chemistry, 2011, # 2, p. 271 - 279
[5] Patent: WO2005/123703, 2005, A2. Location in patent: Page/Page column 207
[6] Molecules, 2010, vol. 15, # 12, p. 9157 - 9173
[7] Journal of Organic Chemistry, 2003, vol. 68, # 8, p. 3327 - 3329
[8] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 8, p. 1077 - 1080
  • 3
  • [ 927-74-2 ]
  • [ 395652-44-5 ]
YieldReaction ConditionsOperation in experiment
74%
Stage #1: at 20℃;
Stage #2: at 20 - 80℃; for 20.50 h;
Example 32; 2-(4-(5-PhgpEl-2H-tetrazol-2-yl)but-1-3TY1)pyLidine; 32(A) 4-(Pyridin-2- )but-3-yn-1-ol; In a dry reaction tube containing in suspension iodide copper (38 mg, 0.2 mmol) and triethylamine (11 mL, 80 mmol), were added 2-bromopyridine (632 mg, 4 mmol) and Pd (PPh3)2Cl2 (140 mg, 0.2 mmol). A yellow suspension is obtained and after a few minutes of stirring at room temperature, was added a solution of but-3-yn-1-ol (280 mg, 4 mmol) in triethylamine (2.2 mL). Immediatly the color of the reaction turns to black. The mixture was stirred at room temperature for 30 min and then at 80°C for 20h. Triethylamine was concentrated under reduced pressure and the residue was dissolved in DCM. The organic layer was washed with saturated NH4CI, water and brine, dried (MgS04) and concentrated. The product was purified by flash chromatography (prepacked 15 g silicagel column, from DCM 100percent to DCM/MeOH : 98/2 as eluent) to afford 440 mg of 4-(pyridin-2-yl)but-3-yn-l-ol (Yield : 74percent) as brown oil. Rf:(DCM/MeOH : 95/5) = 0.5 LCMS (RT) : 0.60min; MS (ES+) gave m/z : 148.1
Reference: [1] Patent: WO2005/123703, 2005, A2. Location in patent: Page/Page column 103-104
  • 4
  • [ 4930-98-7 ]
  • [ 927-74-2 ]
  • [ 395652-44-5 ]
Reference: [1] Green Chemistry, 2018, vol. 20, # 21, p. 4859 - 4864
  • 5
  • [ 5029-67-4 ]
  • [ 927-74-2 ]
  • [ 395652-44-5 ]
YieldReaction ConditionsOperation in experiment
67% With potassium phosphate In water; isopropyl alcohol at 80℃; for 20.00 h; Sealed tube General procedure: In a sealed tube, aryl iodide (1 mmol, 1 equiv.), K3PO4(2 mmol,2 equiv.), catalyst (2 molpercent Pd) were suspended in i-PrOH (3 mL)and H2O (3 mL). The acetylene derivative (1.2 mmol, 1.2 equiv.)was added and the resulting mixture was stirred at 80C for 20 h.After cooling to room temperature, EtOAc (20 mL) and H2O (20 mL)were added and the mixture was filtered over a pad of Celite®.The aqueous layer was extracted twice with EtOAc (2 × 20 mL). Thecollected organics extracts were washed by brine (60 mL), driedon MgSO4, filtered and concentrated under reduced pressure. Thecrude product was purified by flash chromatography.
Reference: [1] Applied Catalysis A: General, 2014, vol. 482, p. 157 - 162
  • 6
  • [ 109-04-6 ]
  • [ 927-74-2 ]
  • [ 395652-44-5 ]
YieldReaction ConditionsOperation in experiment
90% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In 1,4-dioxane at 20℃; Inert atmosphere Under nitrogen atmosphere, and at r.t., CuT (0.06 g, 0.31 mmol), dry Et3N (1.32 mL, 9.49 mmol) and bis-(triphenylphosphine)-palladium chloride (0.13 g, 0.18 mmol) were sequentially added to a solution of 2-bromopyridine (0.60 mL, 6.33 mmol) in 1,4-dioxane (10 mL). Then, but-3-yn-1-ol (0.57 mL, 7.59 mmol) was added dropwise at the same temperature.The resulting reaction mixture was left stirred overnight, then concentrated under reduced pressure, dissolved in EtOAc (80 mL) and washed with H20 (3 x 10 mL). The organic layer was dried over Na2504 and concentrated to dryness to give an oily crude (1.1 g). Purification by typical silica gel flash chromatography using a Teledyne ISCO apparatus (Cy/EtOAc from 90:10 to 30:70) afforded the pure title compound (0.84 g, 90percent), as a white solid. R= 1.25 mm. MS(ESI) m/z: 148 EM-H], 170 EM-Na], 186 EM-K]. ‘H NMR (DMSO-d6): ö 8.55—8.49 (m, 1H),7.76 (td, 1H, J= 7.8, 1.8 Hz), 7.44 (d, 1H, J= 7.8 Hz), 7.33 (ddd, 1H, J= 7.8, 4.9, 1.8 Hz), 4.92 (t, 1H, J= 5.2 Hz), 3.62-3.58 (m, 2H), 2.58 (t, 2H, J= 6.8 Hz).
77% at 0 - 70℃; Example 199 ;3 -Methoxy- N -methyl- N -( 4-(pyridin- 2-yl)but - 3 -ynyl)benzamide; 199(A) 4-(Pyridin-2-yl)but-3-yn-1-01; To a suspension of CuI (301 mg, 1.58 mmol) in TEA (40 mL) were added 2- bromopyridine (5 g, 31.6 mmol), followed by Pd2Cl2(PPh3)2 (1.11 g, 1.58 mmol) to give a yellow orange suspension. After cooling down to 0°C under N2, 3-butyn-l-ol (2.28 g, 31.6 mmol) was added. The resulting reaction mixture turned black and it was stirred overnight at 70°C. The reaction mixture was quenched at 0°C with water, TEA was removed under low pressure, and the organic layer was extracted 3x using DCM, washed with Ammonia, water, brine, dried over MgS04, filtered and concentrated. The crude residue was purified over silicagel chromatography (prepacked 250 g silicagel column, DCM/MeOH : from 99/1 to 95/5 as eluent) to afford 3.60 g of 4- (pyridin-2-yl)but-3-yn-1-ol as a brown oil (Yield : 77percent). LCMS (RT) : 1.58min; MS (ES+) gave m/z : 148 Rf (DCM/MeOH : 95/5) =0.23
Reference: [1] Tetrahedron Letters, 2005, vol. 46, # 10, p. 1717 - 1720
[2] Journal of Organic Chemistry, 2003, vol. 68, # 3, p. 762 - 769
[3] Patent: WO2014/144836, 2014, A2. Location in patent: Paragraph 0526; 0527
[4] European Journal of Organic Chemistry, 2011, # 2, p. 271 - 279
[5] Patent: WO2005/123703, 2005, A2. Location in patent: Page/Page column 207
[6] Molecules, 2010, vol. 15, # 12, p. 9157 - 9173
[7] Journal of Organic Chemistry, 2003, vol. 68, # 8, p. 3327 - 3329
[8] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 8, p. 1077 - 1080
  • 7
  • [ 927-74-2 ]
  • [ 395652-44-5 ]
YieldReaction ConditionsOperation in experiment
74%
Stage #1: at 20℃;
Stage #2: at 20 - 80℃; for 20.50 h;
Example 32; 2-(4-(5-PhgpEl-2H-tetrazol-2-yl)but-1-3TY1)pyLidine; 32(A) 4-(Pyridin-2- )but-3-yn-1-ol; In a dry reaction tube containing in suspension iodide copper (38 mg, 0.2 mmol) and triethylamine (11 mL, 80 mmol), were added 2-bromopyridine (632 mg, 4 mmol) and Pd (PPh3)2Cl2 (140 mg, 0.2 mmol). A yellow suspension is obtained and after a few minutes of stirring at room temperature, was added a solution of but-3-yn-1-ol (280 mg, 4 mmol) in triethylamine (2.2 mL). Immediatly the color of the reaction turns to black. The mixture was stirred at room temperature for 30 min and then at 80°C for 20h. Triethylamine was concentrated under reduced pressure and the residue was dissolved in DCM. The organic layer was washed with saturated NH4CI, water and brine, dried (MgS04) and concentrated. The product was purified by flash chromatography (prepacked 15 g silicagel column, from DCM 100percent to DCM/MeOH : 98/2 as eluent) to afford 440 mg of 4-(pyridin-2-yl)but-3-yn-l-ol (Yield : 74percent) as brown oil. Rf:(DCM/MeOH : 95/5) = 0.5 LCMS (RT) : 0.60min; MS (ES+) gave m/z : 148.1
Reference: [1] Patent: WO2005/123703, 2005, A2. Location in patent: Page/Page column 103-104
  • 8
  • [ 4930-98-7 ]
  • [ 927-74-2 ]
  • [ 395652-44-5 ]
Reference: [1] Green Chemistry, 2018, vol. 20, # 21, p. 4859 - 4864
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