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CAS No. : | 177734-82-6 | MDL No. : | MFCD05662391 |
Formula : | C4H4BClO2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JWVLMZZYJOJCTI-UHFFFAOYSA-N |
M.W : | 162.40 | Pubchem ID : | 22348286 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 39.15 |
TPSA : | 68.7 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.25 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 1.47 |
Log Po/w (WLOGP) : | 0.08 |
Log Po/w (MLOGP) : | -0.2 |
Log Po/w (SILICOS-IT) : | 0.76 |
Consensus Log Po/w : | 0.42 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.12 |
Solubility : | 1.24 mg/ml ; 0.00762 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.52 |
Solubility : | 0.491 mg/ml ; 0.00302 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.16 |
Solubility : | 11.2 mg/ml ; 0.0687 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.62 |
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: |
* 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 |
---|---|---|
14% | With caesium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; ethanol; water; at 160.0℃; for 0.08333330000000001h;Microwave irradiation; | [[00136]] Into a dry microwave vial under N2 was added 6-Bromo- [4- [1- (3-PHENYL-ALLYL)-PIPERIDINE-4-YLAMINO]-CHROMEN-2-ONE] (20 mg, 0.046mmol), Pd (PPh3) Cl2 (about 1 mol%), and [CS2CO3] (17.8 mg, 0.0547mmol) in [DME/H2O/ETOH] (7/3/2,. 5 mL). 2-chloro-3- thiophene boronic acid (6.3 mg, 0.046mmol) was added and the solution was heated in the microwave for 5 minutes at 160 [C,] filtered, and was purified by Prep HPLC to give 3.7 mg (14 %) of the desired compound as the TFA salt. MS (ESI (+) [Q1MS] m/z 475 (M-2H) [+] [; 1H] NMR (300 MHz, DMSO) 8 ppm 1.82-1. 89 (m, 2H), 2.25 (br d, 2H), 3.15-3. 22 (m, 2H), 3.61 (br d, 2H), 3.78-4. 01 (m, 3H), 5.45 (s, [1] H), 6.36-6. 42 (m, [1] H), 6.90 (d, [1] H), 7.21-7. 82 (m. 10H), 8.30 (d, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 1,4-dioxane; | Example 289 7-(2-Chlorothiophen-3-yl)-2-(2-quinolin-2-yl-ethyl)-2,3-dihydro-isoindol-1-one The title compound was prepared in analogy to the process described in Example 281 but using <strong>[177734-82-6]2-chlorothiophen-3-ylboronic acid</strong> (16.2 mg, 0.1 mmol) dissolved in dioxane (0.3 mL) instead of 5-cyanothiophen-2-ylboronic acid (15.3 mg, 0.1 mmol) dissolved in dioxane (0.3 mL). Yield: 5.6 mg, 17%. 1H NMR (400 MHz, DMSO/D2O) delta ppm 8.28 (d, J=8.54 Hz, 1H) 7.91 (dd, J=19.23, 7.93 Hz, 2H) 7.69-7.75 (m, 1H) 7.35-7.67 (m, 5H) 7.29-7.34 (m, 1H) 6.93 (d, J=5.80 Hz, 1H) 4.53 (s, 2H) 3.96 (t, J=7.17 Hz, 2H) 3.27 (t, J=7.17 Hz, 2H); MS (ESI) m/z 405 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In 1,2-dimethoxyethane; water; at 130.0℃; for 0.166667h;Microwave irradiation; | 4-Bromobenzene-1,2-diamine (600 mg), <strong>[177734-82-6](2-chlorothiophen-3-yl)boronic acid</strong> (1.04 g) andbis(triphenylphosphine)palladium(ll) dichloride (113 mg) were solubilised in 1,2- dimethoxyethane (20 ml) and an aqueous solution of K2C03 (4.8 ml, 2.0 M) was added. The reaction mixture was stirred for 10 mm under microwave irradiation at 130D. The mixture was filtered and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel to give 250 mg of the title compound.LC-MS (Method 2): Rt = 1.01 mm; MS (ESIpos): m/z = 225 [M+H]1H-NMR (400MHz, DMSO-d6): oe [ppm]= 4.54-4.68 (m, 4H), 6.55 (d, 1H), 6.62 -6.66 (m, IH),6.78 (d, 1H), 7.06 (d, IH), 7.43 (d, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10.41% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride; In 1,4-dioxane; water; at 70.0℃; for 12.0h; | Cesium fluoride (173.71 mg, 1.14 mmol, 2.00 eq) and Pd(dppf)Cl2 (8.37 mg, 11.44 mumol, 0.02 eq) were added to a mixed solution of (2S)-2-[(2-chloro-7,8-dihydro-5H-1,6-naphthyridin-6-yl)boxylphenethyl]-2-methyl-6-nitro-3H-imidazo[2,1-b]oxazole (200.00 mg, 571.80 mumol, 1.00 eq) and (2-chloro-3-thienyl) boronic acid (92.86 mg, 571.80 mumol, 1.00 eq) in dioxane (3.00 mL) and water (300.00 muL). The mixture was stirred at 70 C for 12 hours. Water (50 mL) was added to quench the reaction mixture and extracted with ethyl acetate (50 mL * 3). The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure to give a residue. The residue was separated and purified by preparative separation chromatography (GX-F;Phenomenex Synergi C18 150*25*10um; acetonitrile 30%-60%; ACN (0.225% fomic acid); 25mL/min) to deliver (2S)-2-((2-(2-chlorothiophen-3-yl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methyl)-2-methyl-6-nit ro-2,3-dihydroimidazo[2,1-b]oxazole compound 53 (26.30 mg, 59.55 mumol, 10.41% yield, 97.8% purity). 1H NMR (400 MHz, METHANOL-d4): delta 7.82 (s, 1H), 7.65 (d, J = 6.15 Hz, 2H), 7.39 (d, J = 5.90 Hz, 1H), 7.31 (d, J = 5.77 Hz, 1H), 4.42 (d, J = 10.54 Hz, 1H), 4.15 (d, J = 10.54 Hz, 1H), 3.95 (s, 2H), 3.25-2.81 (m, 6H), 1.69 (s, 3H). LCMS (ESI) m/z: 432.2 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride; In toluene; for 1.0h;Reflux; Inert atmosphere; | A mixture of methyl 5-bromo-2-cyclopropyl-pyrimidine-4-carboxylate (700 mg,), (2-chloro-3- thienyl)boronic acid (660 mg,), CsF (1 .24 g,) and PdCl2dppf (398 mg,) in toluene (30 mL) is heated under reflux under an atmosphere of argon for 1 h. Water and EtOAc are added, the phases are separated and organic phase is dried over Mg504. The solids are removed via filtration and resulting solution is concentrated under reduced pressure. Column chromatography ofthe crude product (ISCO-CombiFlash Rf, cyclohexane/EtOAc) yields the title compound (200 mg, yield 25%) as a yellow oil.1H NMR (400 MHz, CDCI3): 68.68 (s, 1H), 7.20 (d, J = 5.7Hz, 1H), 6.92 (d, J = 5.8 Hz, 1H),3.85 (s, 3H), 2.42-2.36 (m, 1H), 1.26-1.13 (m, 4H) ppm; MS (ESI) m/z295.1 [M + Hj. |
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