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Chemical Structure| 220465-43-0
Chemical Structure| 220465-43-0
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Product Details of [ 220465-43-0 ]

CAS No. :220465-43-0 MDL No. :MFCD03095175
Formula : C8H8BNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :USJUQEVUEBCLLR-UHFFFAOYSA-N
M.W : 160.97 Pubchem ID :2763173
Synonyms :

Safety of [ 220465-43-0 ]

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 [ 220465-43-0 ]

* 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.

  • Upstream synthesis route of [ 220465-43-0 ]
  • Downstream synthetic route of [ 220465-43-0 ]

[ 220465-43-0 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 220465-43-0 ]
  • [ 387-43-9 ]
Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 14, p. 3251 - 3256
  • 2
  • [ 52488-36-5 ]
  • [ 220465-43-0 ]
YieldReaction ConditionsOperation in experiment
70%
Stage #1: With potassium hydride In diethyl ether at -78℃; for 0.75 h;
Stage #2: With boric acid tributyl ester; tert.-butyl lithium In diethyl ether; pentane at -78 - 20℃; for 21 h;
Stage #3: With phosphoric acid In diethyl ether; pentane at 0℃; for 0.5 h;
To a round bottom flask at O0C containing a mixture of potassium hydride (35 wt. percent dispersion in mineral oil, 4.5 g, 39.3 mmol) and ether (105 mL) was added a <n="198"/>solution of 4-bromo-1 H-indole (7.0 g, 35.7 mmol) in ether (35 mL) dropwise. The reaction was transferred to a -780C bath and stirred for 45 min followed by addition of a -780C solution of f-BuLi (1.7 M in pentane, 46.2 mL, 78.5 mmol) via cannulation. To this slurry at -780C was added tributyl borate (29 mL, 107.1 mmol). The reaction warmed to r.t. over 21 h and then was placed in a O0C bath followed by addition of a solution of H3PO4 (350 mL, 1M). The mixture was stirred for 30 min., extracted with ether, dried over Na2SO4, and concentrated in vacuo to afford 74d (4.01 g, 70percent) as a beige solid. 1HNMR ((CD3)2CO/ 15percent D2O, 400 MHz) 5.37-5.33 (m, 2H), 5.13 (s, 1H), 4.90 (t, 1 H), 4.76 (s, 1 H), 1.27 (s, 3H); MS (M+1 )+ m/z calcd for C8H8BNO2+ = 161.0, found m/z = not found.
Reference: [1] Journal of Organic Chemistry, 1999, vol. 64, # 4, p. 1372 - 1374
[2] Organic Letters, 2004, vol. 6, # 1, p. 3 - 5
[3] Patent: WO2009/73777, 2009, A1, . Location in patent: Page/Page column 195-196
  • 3
  • [ 121-43-7 ]
  • [ 220465-43-0 ]
Reference: [1] Patent: US2005/245524, 2005, A1, . Location in patent: Page/Page column 74
  • 4
  • [ 52488-36-5 ]
  • [ 688-74-4 ]
  • [ 220465-43-0 ]
Reference: [1] Patent: US6307056, 2001, B1,
  • 5
  • [ 942-24-5 ]
  • [ 220465-43-0 ]
Reference: [1] Organic Letters, 2004, vol. 6, # 1, p. 3 - 5
  • 6
  • [ 101909-43-7 ]
  • [ 220465-43-0 ]
Reference: [1] Organic Letters, 2004, vol. 6, # 1, p. 3 - 5
  • 7
  • [ 1233339-68-8 ]
  • [ 220465-43-0 ]
  • [ 1233339-22-4 ]
YieldReaction ConditionsOperation in experiment
51% With sodium carbonate In 1,2-dimethoxyethane; water at 90℃; Example 3.014-{4-r(3R)-3-Methylmorpholin-4-yl1-6-ri-(methylsulfonyl)cvclopropyl1pyrimidin-2-yl}- lH-indoleBis(triphenylphosphine)palladium chloride (1.692 g, 2.41 mmol), (R)-4-(2-chloro-6-(l- (methylsulfonyl)cyclopropyl)pyrimidin-4-yl)-3-methylmorpholine (8.00 g, 24.11 mmol), IH- indol-4-ylboronic acid (4.27 g, 26.52 mmol) and 2M aqueous sodium carbonate (36.2 rnL, 72.33 mmol) were suspended in DME:water 4:1 (170 mL) and heated to 90 0C overnight. The DME was removed and the reaction mixture diluted with EtOAc (100 mL). The mixture was washed with water (2 x 100 mL), the organics separated, filtered through a pad of Celite and concentrated in vacuo on to silica. The residue was purified by chromatography on silica with an elution gradient of 0 to 10percent EtOAc in DCM. Fractions containing product were combined and evaporated. The residue was purified by chromatography on silica eluting with a gradient of 0-25percent EtOAc in DCM. Fractions containing product were combined and evaporated onto reverse phase Cl 8 silica. The crude product was purified by reverse phase using a 415g HP Cl 8 column using decreasingly polar mixtures of water (containing 1percent NH3) and MeCN as eluents. Fractions containing product were combined and evaporated. The residue was taken up in dry MeOH and dried over MgSO4. The mixture was filtered and the solvent evaporated, leaving a gum. The gum was dissolved in DCM (500 mL), filtered and the solvent removed under reduced pressure. The residue was dissolved in MeOH (50 mL) and allowed to stir at RT overnight. The resultant precipitate was collected by filtration to afford the title compound (5.1O g, 51percent); 1H NMR (400 MHz, DMSO-/): 1.29 (3H, d), 1.57 - 1.64 (2H, m), 1.68 - 1.78 (2H, m), 3.24-3.31 (IH, td), 3.29 (3H, s), 3.51 (IH, td), 3.67 (IH, dd), 3.80 (IH, d), 3.93 - 4.06 (IH, dd), 4.21 (IH, d), 4.61 (IH, bs), 6.85 (IH, s), 7.21 (IH, t), 7.32 (IH, t), 7.46 (IH, t), 7.56 (IH, d), 8.06 (IH, dd), 11.25 (IH, s); m/z: (ESI+) MH+, 413.12. Chiral HPLC: (HPI lOO System 4, 5μm Chiralpak AS-H (250mm x 4.6mm) column eluting with iso- Hexane/EtOH/TEA 60/40/0.1) Rf, 8.815 >99percent.
Reference: [1] Patent: WO2010/73034, 2010, A1, . Location in patent: Page/Page column 68-69
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 5, p. 2125 - 2138
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