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[ CAS No. 847560-50-3 ] {[proInfo.proName]}

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Chemical Structure| 847560-50-3
Chemical Structure| 847560-50-3
Structure of 847560-50-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 847560-50-3 ]

CAS No. :847560-50-3 MDL No. :MFCD18731017
Formula : C14H19BO3 Boiling Point : -
Linear Structure Formula :- InChI Key :LUIMXIDOSHHWCZ-UHFFFAOYSA-N
M.W : 246.11 Pubchem ID :59519267
Synonyms :

Calculated chemistry of [ 847560-50-3 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.5
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 73.27
TPSA : 35.53 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.86 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.74
Log Po/w (WLOGP) : 2.11
Log Po/w (MLOGP) : 1.31
Log Po/w (SILICOS-IT) : 2.52
Consensus Log Po/w : 1.74

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.21
Solubility : 0.153 mg/ml ; 0.000621 mol/l
Class : Soluble
Log S (Ali) : -3.14
Solubility : 0.178 mg/ml ; 0.000723 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.34
Solubility : 0.0113 mg/ml ; 0.0000459 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.0

Safety of [ 847560-50-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 847560-50-3 ]

* 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 [ 847560-50-3 ]
  • Downstream synthetic route of [ 847560-50-3 ]

[ 847560-50-3 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 36276-24-1 ]
  • [ 73183-34-3 ]
  • [ 847560-50-3 ]
YieldReaction ConditionsOperation in experiment
91.39%
Stage #1: With potassium acetate In 1,4-dioxane for 0.333333 h; Inert atmosphere
Stage #2: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane at 90℃;
To a stirred solution of intermediate 4a (3.0 g, 15.1 mmol) in 1,4 dioxone (30 mL), bis(pinocolate)diboran (4.5 g, 17.7 mmol) and potassium acetate (2.98 g, 30.4 mmol) was added. The resultant was degasified with nitrogen for 20 mm. Then, Pd(dppf)C12 (0.62 g, 0.75 mmol) was added to it. It was heated at 90°C over night. The reaction mixture was diluted with water and extracted with ethyl acetate; the organic layer waswashed with water and brine solution and was then concentrated. The product was purified by combiflash to yield the title product (3.4 g, 91 .39percent) as a yellow semi solid.LCMS: (M+H) =247.2; 1H NMR: (ODd3, 300MHz) 69.99(s, 1H), 8.26 (5, 1H), 7.82- 7.85 (dd, 1H), 7.26-7.33 (m, 1H), 2.62 (5, 3H), 1.37 (5, 12H).
91.39%
Stage #1: With potassium acetate In 1,4-dioxane for 0.333333 h; Inert atmosphere
Stage #2: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane at 90℃;
To a stirred solution of intermediate 4a (3.0 g, 15.1 mmol) in 1,4 dioxone (30 mL), bis(pinocolate)diboran (4.5 g, 17.7 mmol) and potassium acetate (2.98 g, 30.4 mmol)was added. The solution was then degasified with nitrogen for 20 mm. Then, Pd(dppf)C12 (0.62 g, 0.75 mmol) was added. It was heated at 90°C over night. The reaction mixture was diluted with water and extracted with ethyl acetate; the organic layer was washed with water, brine solution and concentrated. The product was purified by combif lash to yield the title product (3.4 g, 91 .39percent) as a yellow semi solid.LCMS: (M+H) =247.2; 1H NMR: (ODd3, 300MHz) 6 9.99 (5, 1 H), 8.26 (5, 1 H), 7.82-7.85 (dd, 1H), 7.26-7.33 (m, 1H), 2.62 (5, 3H), 1.37 (5, 12H).
85% With potassium acetate In DMF (N,N-dimethyl-formamide) at 85℃; for 2.5 h; Step 2 4-METHYL-3- (4, 4, 5, 5-TETRAMETHYL- [1, 3,2] dioxaborolan-2-yl)-benzaldehyde A mixture of 3-Bromo-4-methyl-benzaldehyde (3.105 g; 15.6 MMOL), bis (pinacolato) diboron (4.29 g; 16.86 MMOL) and Potassium acetate (4.59g ; 46.8 MMOL) in DIMETHYLFORMAMIDE (60 mL) was degassed by evacuation-nitrogen purge (3 cycles), followed by bubbling nitrogen gas through the stirred reaction mixture for 5 minutes. Palladium acetate (0.120 g; 0.536 MMOL) was added and reaction mixture was heated to 85 degrees C (oil-bath temperature) for 2.5 hours. Reaction mixture was allowed to cool to room temperature and DMF removed in vacuo. The residue was partitioned between ethyl acetate (150 mL) and water (150 mL) and the mixture was filtered through a pad of celite to remove black Pd solids. Filter cake was washed with ethyl acetate (2 x 50 mL) and combined filtrate phases were separated and the organic phase was washed with water (2 x 150 mL) then saturated sodium chloride solution (150 mL). Organic phase was dried over NA2SO4 and filtered, filtrate solvents removed in vacuo to afford a yellow oil which was purified by flash chromatography on silica gel (50g IST Flash ; eluting 0 to 10percent ethyl acetate in hexane) to afford product as a colourless solid Yield : 4.58 g; 85percent LC-MS retention time = 2.799 min; [M+H] + 247 1H NMR (400 MHz, CDCI3) 8 1.36 (s, 12H), 2.62 (s, 3H), 7.31 (d, 1H, J = 7.88 Hz), 7. 83 (dd, 1H, J = 7.88 and 1.9 Hz), 8.25 (d, 1H, J = 1.9 Hz), 9.98 (s, 1 H)
Reference: [1] Patent: WO2014/202580, 2014, A1, . Location in patent: Page/Page column 79
[2] Patent: WO2014/202528, 2014, A1, . Location in patent: Page/Page column 65
[3] Patent: WO2005/21552, 2005, A1, . Location in patent: Page/Page column 62-63
[4] Journal of Medicinal Chemistry, 2010, vol. 53, # 10, p. 3973 - 4001
  • 2
  • [ 104-87-0 ]
  • [ 847560-50-3 ]
Reference: [1] Patent: WO2014/202580, 2014, A1,
[2] Patent: WO2014/202528, 2014, A1,
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