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[ CAS No. 903550-26-5 ] 1-(Tetrahydropyran-2-yl)-1H-pyrazole-5-boronic acid pinacol ester

Cat. No.: A103483
Chemical Structure| 903550-26-5
Chemical Structure| 903550-26-5
Structure of 903550-26-5 * Storage: Inert atmosphere,2-8°C
Purity Size Price USA Stock *0-1 Day Global Stock *5-7 Days Quantity
97% 1g $6.00 Inquiry Inquiry
97% 5g $8.00 Inquiry Inquiry
97% 10g $10.00 Inquiry Inquiry
97% 25g $24.00 Inquiry Inquiry
97% 100g $59.00 Inquiry Inquiry
97% 500g $294.00 Inquiry Inquiry

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Product Details of [ 903550-26-5 ]

CAS No. :903550-26-5 MDL No. :MFCD09037501
Formula : C14H23BN2O3 Boiling Point : No data available
Linear Structure Formula :- InChI Key :ZZRFDLHBMBHJTI-UHFFFAOYSA-N
M.W : 278.16 Pubchem ID :11587208
Synonyms :
Chemical Name :1-(Tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Calculated chemistry of [ 903550-26-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.79
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 78.16
TPSA : 45.51 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 : Yes
Log Kp (skin permeation) : -6.56 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.02
Log Po/w (WLOGP) : 1.56
Log Po/w (MLOGP) : 0.98
Log Po/w (SILICOS-IT) : 0.86
Consensus Log Po/w : 1.08

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.89
Solubility : 0.358 mg/ml ; 0.00129 mol/l
Class : Soluble
Log S (Ali) : -2.6
Solubility : 0.694 mg/ml ; 0.00249 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.9
Solubility : 0.346 mg/ml ; 0.00124 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 4.11

Safety of [ 903550-26-5 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 903550-26-5 ]

* 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.

  • Downstream synthetic route of [ 903550-26-5 ]

[ 903550-26-5 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 903550-26-5 ]
  • [ 175205-81-9 ]
  • [ 1381972-62-8 ]
YieldReaction ConditionsOperation in experiment
89% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; at 100℃; for 2h; <strong>[175205-81-9]2-bromo-4-(trifluoromethyl)pyridine</strong> (2.0 g, 8.85 mmol) was added to a mixture of 1-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (2.85 g,9.73 mmol,) tetrakis(triphenylphosphine)palladium(0) (511 mg, 0.44 mmol,) and potassium carbonate (3.67 g 26.55 mmol,) in ethanol (10 mL) and toluene (10 mL). The mixture was stirred at 100°C for 2h. The reaction was cooled down and water was added. The aqueous phase was extracted with 3X50 mL of dichloromethane. The organic phase was dried with MgSO4, filtered and concentrated. Purification by flash chromatography (100percent heptane to 100percent ethyl acetategradient, 40 g column) afforded 2.34 g (89percent) of 2-(2-tetrahydropyran-2-ylpyrazol-3-yl)-4-(trifluoromethyl)pyridine as a yellow oil. LCMS (Method Shimadzu): RT = 1.45 min, m+H = 298.1. 1H NMR (400 MHz, Chloroform-d) delta 8.87 (d, J = 5.0 Hz, I H), 7.86 (d, J = 1.5 Hz, 1H), 7.63 (dd, J = 14.6,2.2Hz, 1H), 7.48 (dd, J = 5.2, 1.6 Hz, 1H), 6.70 (d, J = 1.9 Hz, 1H), 6.14 (dd, J = 10.0,2.5Hz, 1H),4.04(ddt,J= 11.5,4.3,2.1 Hz, 1H),3.61 (td,J= 11.4,2.6Hz, 1H),2.63-2.48(m, 1H),2.17-1.99 (m, 2H), 1.83 - 1.62 (m, 2H), 1.58 (s, 1H).
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 90℃; for 2h; General procedure: Pd(PPh3)4 (9.23 g, 7.99 mmol) and a 2 mol/L aqueous Na2CO3solution (2.4 L) were added to an EtOH (1.6 L)/ toluene (1.6 L)mixed solution of 1 (500 g, 1.8 mol) and 2-bromo-5-fluoropyridine(281.2 g, 1.60 mol), and the mixture was heated to 90 C and stirredfor 2 h. After standing to cool at 0 C, water was added to thereaction mixture, followed by extraction with EtOAc. The extractedorganic layer was distilled off under reduced pressure. Theobtained residue was stirred in EtOAc (1.2 L), and NH silica gelwas added thereto. The mixture was stirred at room temperaturefor 1 h. Then, the silica gel was filtered off, and the solvent was distilledoff under reduced pressure to obtain 5-fluoro-2-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)pyridine as a brown oil.A 4 mol/L HCl?EtOAc solution (1.2 L) was added to a solution of5-fluoro-2-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)pyridinein MeOH (1.0 L), and the mixture was stirred at room temperaturefor 5 h. The deposited solid was then collected by filtration. Theobtained solid was stirred in water (2.0 L), and an 8 mol/L aqueousNaOH solution (0.3 L) was added thereto under ice cooling. Themixture was extracted with EtOAc, and the solvent was distilledoff under reduced pressure. The obtained residue was stirred for1 h in Et2O. Then, the deposited solid was collected by filtrationand dried by heating under reduced pressure to obtain the titlecompound 2a as a colorless powder (185 g, 71percent over 2 steps).
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