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CAS No. : | 886547-94-0 | MDL No. : | MFCD09999194 |
Formula : | C19H21BN2O4S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KZANVIJXSQABKR-UHFFFAOYSA-N |
M.W : | 384.26 | Pubchem ID : | 45588137 |
Synonyms : |
|
Num. heavy atoms : | 27 |
Num. arom. heavy atoms : | 15 |
Fraction Csp3 : | 0.32 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 105.28 |
TPSA : | 78.8 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.17 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 3.48 |
Log Po/w (WLOGP) : | 3.65 |
Log Po/w (MLOGP) : | 2.66 |
Log Po/w (SILICOS-IT) : | 1.2 |
Consensus Log Po/w : | 2.2 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.63 |
Solubility : | 0.00905 mg/ml ; 0.0000236 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.82 |
Solubility : | 0.00585 mg/ml ; 0.0000152 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -6.06 |
Solubility : | 0.000333 mg/ml ; 0.000000867 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.71 |
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: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With potassium acetate In N,N-dimethyl-formamide at 90℃; for 2 h; | A solution of 3-iodo-1-(phenylsulfonyl)-1 H-pyrrolo[2,3-b]pyridine (4.2 g , 10.9 mmol), bis-pinacolatodiboron (5.6 g, 21.8 mmol), potassium acetate (3.2 g, 32.7 mmol) and Pd(dppf)CI2-complex with dichloromethane (788 mg, 0.982 mmol) inDMF (40 mL) was stirred at 90 0C for 2h in a sealed tube. The solution was cooled by the addition of ice and made basic to pH 12-14 with 6N NaOH. The aqueous phase was extracted with DCM then made acidic to pH ~1 with 6N HCI. The aqeous phase was extracted several times with DCM and the combined fractions were dried (Na2SO4) and concentrated affording the title compound (4.2g, quant.) as a brown solid which was used without further purification; LCMS (m/e) 386 (boronic ester M+H)+, 303 (boronic acid M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With potassium acetate In tetrahydrofuran for 24 h; Heating / reflux | A mixture of compound Id (50.78 g), bis(pinacolato)diboron (42.22 g), [l,r-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1:1 complex with dichloromethane, 12.32 g) and potassium acetate (44.46 g) in THF (3OO mL) was refluxed for 24 hrs. The. reaction was quenched with water and extracted, with ethyl acetate. The combined organic phase was concentrated and the residue was purified on silica gel column (eluted with 100percent dichloromethane and 2percent methanol in dichloromethane) to provide l-benzenesulfonyl-3-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-lH-pyrrolo[2,3-b]pyridine (Ie) (22.10 g, 38percent) as a white solid. 1H NMR (400MHz, CDCl3) δ 8.42 (d, J = 4.8 Hz, IH), 8.21 (m, 3H), 8.15 (s, IH), 7.57 (t, J = 7.6 Hz, IH), 7.48 (t, J = 7.6 HZ, 2H), 7.35 (dd, J = 8.0 Hz, 4.8 Hz, IH). MS (ESI) m/z: 385 (M+H)+. |
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