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CAS No. : | 321438-86-2 | MDL No. : | MFCD03788238 |
Formula : | C6H8BNO2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UXWKVPJOPVIIRU-UHFFFAOYSA-N |
M.W : | 169.01 | Pubchem ID : | 2762705 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.17 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 45.78 |
TPSA : | 78.65 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) : | -6.9 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 0.6 |
Log Po/w (WLOGP) : | -0.52 |
Log Po/w (MLOGP) : | -0.75 |
Log Po/w (SILICOS-IT) : | -0.66 |
Consensus Log Po/w : | -0.26 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.54 |
Solubility : | 4.9 mg/ml ; 0.029 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.83 |
Solubility : | 2.53 mg/ml ; 0.0149 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.41 |
Solubility : | 6.62 mg/ml ; 0.0392 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.15 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
81% | To a stirred solution of 50 (2.74 g, 13.43 mmol) and triisopropylborate (3.72 mL, 16.11 mmol) in a mixture of anhydrous toluene/THF (20 mL/5 mL) at-40 under nitrogen was added dropwise a solution of n-BuLi (6.98 mL, 17.45 mmol, 2.5M in hexanes). After stirring for 1 h at-40CC, the mixture was allowed to warm to room temperature and quenched with 2N HCI. The resultant suspension was filtered ; the precipitate was rinsed with H20 and AcOEt. The filtrate was neutralized with 1N NaOH (pH 7) and extracted with AcOEt. The organic layer and the precipitate were combined, solvent was evaporated and the solid residue was triturated with MeCN-MeOH to afford the title compound 51 (1.84 g, 10.88 mmol, 81% yield) as a pale yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | Stage #1: 6-(methylthio)pyridin-3-ylboronic acid; 4-[(4-chloro-pyrimidin-2-ylamino)-methyl]-benzoic acid methyl ester With sodium carbonate In water; acetonitrile at 90 - 100℃; for 24h; Stage #2: With sodium hydroxide; water In acetonitrile at 90 - 100℃; for 2h; Stage #3: With hydrogenchloride In water | 14; 45.3 To a degassed stirred suspension of a mixture of 51 (593 mg, 3.51 mmol), 45b (500 mg, 1.80 mmol) and solution of Na2CO3 (15 mL, 0.4M) in acetonitrile (15 mL) at room temperature Pd (PPh3) 4 (126 mg, 0.11 mmol) was added. The reaction mixture was heated at 90- 95 for 24 h under nitrogen. Then, 1M NaOH (amount) was added and the heating was continued for additional 2 h. After cooling to the room temperature the reaction mixture was filtered, filtrate was extracted with AcOEt, the aqueous layer was collected, filtered, concentrated and acidified with 2N HCI (pH at 5-6). A precipitate was formed which was collected by filtration and dried to afford the title compound 52 (396 mg, 1.12 mmol, 62% yield) as a beige solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.78 g | With palladium diacetate; triphenylphosphine In tetrahydrofuran; methanol at 100℃; for 1h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | With sodium carbonate In 1,4-dioxane; water at 100℃; for 1h; Microwave irradiation; | 59 To a mixture of 1-benzenesulfonyl-2-[2-cyclopentyl-1-(toluene-4-sulfonyloxy)-vinyl]-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid methyl ester (prepared as in Example 3, 0.90 g, 1.55 mmol), 2-(methylsulfanyl)pyridine-5-boronic acid hydrate (0.52 g, 3.1 mmol) and dichlorobis(triphenylphosphine)palladium (II) (108 mg, 0.15 mmol) in dioxane (6 mL) was added an aqueous sodium carbonate solution (2 M, 3.1 mL). The resulting mixture was subjected to microwave irradiation for 60 min at 100° C. The mixture was diluted with ethyl acetate (150 mL), washed with a saturated aqueous sodium bicarbonate solution (2×30 mL), brine, dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, 25% ethyl acetate/hexanes) afforded 1-benzenesulfonyl-2-[2-cyclopentyl-1-(6-methylsulfanyl-pyridin-3-yl)-vinyl]-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid methyl ester (300 mg, 36%) as a white solid: LC/MS m/e calcd for C28H27N3O4S2 [M+H]+ 534.67, observed 534.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88.7% | With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In tetrahydrofuran; water at 70℃; for 12h; Inert atmosphere; | 3.1.2. General Procedure for Synthesis of Compounds 5a-j General procedure: A mixture of compound 4 (100 mg, 0.29 mmol), aryl boronic acid (0.35 mmol), bis(triphenylphosphine)palladium(II) dichloride (9 mg, 0.013 mmol) and K2CO3 (71 mg, 0.52 mmol) was placed in a mixed solvent of THF and water (4:1, v/v, 10 mL). N2 gas was bubbled into this mixture for 10 min, and then the mixture was heated at 70 °C while stirring under N2 for 12 h. The reaction mixture was left to cool at room temperature, and extracted with ethyl acetate (100 mL × 3). The combined organic extracts were dried over anhydrous MgSO4 and evaporated under vacuum. The target compounds 5a-j were separated in pure form by column chromatography (silica gel) using the proper ratio of ethyl acetate and n-hexane. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With lumiflavin; ammonium formate In acetic acid methyl ester; water for 16h; Inert atmosphere; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With lumiflavin In aq. phosphate buffer for 6h; Irradiation; Inert atmosphere; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With [bis(triphenylphosphine)](o-tolyl)chloronickel; 2,2-Dimethyl-1,3-propanediol; N-ethyl-N,N-diisopropylamine; 1,4-di(diphenylphosphino)-butane In 2-methyltetrahydrofuran; lithium hydroxide monohydrate at 70℃; for 20h; Inert atmosphere; Glovebox; Sealed tube; |
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