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CAS No. : | 1257431-63-2 | MDL No. : | MFCD15143417 |
Formula : | C14H22BNO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FIWGJYZBBBBXPY-UHFFFAOYSA-N |
M.W : | 263.14 g/mol | Pubchem ID : | 53398528 |
Synonyms : |
|
Num. heavy atoms : | 19 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.64 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 76.34 |
TPSA : | 51.58 Ų |
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) : | -6.81 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 1.54 |
Log Po/w (WLOGP) : | 1.5 |
Log Po/w (MLOGP) : | 0.55 |
Log Po/w (SILICOS-IT) : | 1.58 |
Consensus Log Po/w : | 1.03 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.54 |
Solubility : | 0.753 mg/ml ; 0.00286 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.23 |
Solubility : | 1.54 mg/ml ; 0.00586 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.88 |
Solubility : | 0.0351 mg/ml ; 0.000133 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 3.18 |
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: |
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* 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 |
---|---|---|
With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 90℃;Inert atmosphere; | Purge with a mixture of 2-(5-bromo-3-pyridyl)propan-2-ol (18.5 g, 85.7 mmol), bis(pinacolato)diboron (44 g, 171 mmol, 2 eq.) and potassium acetate (25.2 g, 257 mmol, 3 eq.) in 1,4-dioxane (428 mL) in nitrogen thoroughly. Add (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) chloride (3.5 g, 4.3 mmol) and evacuate and purge the reaction twice with nitrogen. Heat the mixture at 90 C. overnight. Cool and dilute with ethyl acetate (1 L) and sonicate for 30 minutes. Filter through a pad of Celite and dry the liquid filtrate over sodium sulfate. After filtration, concentrate the organic liquid and re-dissolve residue in ethyl acetate (1 L) and filter again through a pad of Celite. Concentrate the filtrate and suspend the residue in diethyl ether (100 mL) followed by hexane (700 mL). Sonicate briefly and filter to obtain solid residue to afford the titled compound as a crude solid (18.5 g). MS (ESI) m/z (M+H)+264.0. | |
With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80℃; for 4.0h; | To a 5000-mL 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen were added a solution of the title compound from Example 22 Step C (160 g, 395 mmol) in 1,4-dioxane (2000 mL), 4,4,5,5-tetramethyl-2-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)-l,3,2-dioxaborolane (240 g, 498 mmol), potassium acetate (240 g, 1.63 mol), and PdCl2(dppf) (30 g, 23 mmol). The resulting solution was stirred for 4 hours at 80 C. The reaction was then cooled to room temperature, filtered and concentrated under reduced pressure. The residual solution was diluted with hexanes and filtered. HCl gas was bubbled through the filtrate. The resulting mixture was filtered, and the solids diluted with dichloromethane, then concentrated under reduced pressure. The residue was diluted with H20, and washed sequentially with diethyl ether, dichloromethane, and hexanes. The aqueous layer was adjusted to pH 7-8 with saturated aqueous sodium carbonate solution, then extracted with dichlormethane. The organic extracts were combined, dried and concentrated under vacuum to afford the title compound: 1H NMR (400 MHz, CDC13): δ 8.83 (s, 1 H), 8.19 (s, 1 H), 1.62 (s, 6 H), | |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 100℃; for 15.0h;Inert atmosphere; | A reaction vessel containing a mixture of 2-(5-bromopyridin-3-yl)propan-2-ol (0.5 g, 2.31 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (2.4 g, 9.2 mmol), and potassium acetate (0.612 g, 6.9 mmol) in 1,4-dioxane (20 mL) was purged with argon for 10 min. Next, [l,l-bis(diphenylphosphino)-ferrocene]dichloropalladium (II) (0.190 g, 0.23 mmol) was added and the reaction mixture was heated at 100 C for 15 h. The reaction mixture was cooled to room temperature then filtered through a bed of CELITE and the bed was washed with ethyl acetate. The filtrate was concentrated under reduced pressure to afford the crude product 2-(5-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)pyridin-3-yl)propan-2-ol. MS (M+l): 265.1. |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80℃; for 4.0h;Inert atmosphere; | To a 5000-mL 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen were added a solution of the title compound from Example 2 Step C (160 g, 395 mmol) in 1,4-dioxane (2000 n L), 4,4,5,5-tetramethyl-2-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)-l,3,2-dioxaborolane (240 g, 498 mmol), potassium acetate (240 g, 1.63 mol), and PdCl2(dppf) (30 g, 23 mmol). The resulting solution was stirred for 4 hours at 80 C. The reaction was then cooled to room temperature, filtered and concentrated under reduced pressure. The residual solution was diluted with hexanes and filtered. HCl gas was bubbled through the filtrate. The resulting mixture was filtered, and the solids diluted with dichloromethane, then concentrated under reduced pressure. The residue was diluted with H20, and washed sequentially with diethyl ether, dichloromethane, and hexanes. The aqueous layer was adjusted to pH 7-8 with saturated aqueous sodium carbonate solution, then extracted with dichlormethane. The organic extracts were combined, dried and concentrated under vacuum to afford the title compound: 1H NMR (400 MHz, CDC13): δ 8.83 (s, 1 H), 8.19 (s, 1 H), 1.62 (s, 6 H), 1.36 (s, 12 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With potassium fluoride;tris-(dibenzylideneacetone)dipalladium(0); tri tert-butylphosphoniumtetrafluoroborate; In tetrahydrofuran; water; at 65 - 70℃;Inert atmosphere; Sealed tube; | Dissolve 8-bromo-1-[(2S)-2-methoxypropyl]-3-methyl-imidazo[4,5-c]quinolin-2-one (0.600 g, 1.7 mmol) and 2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridyl]propan-2-ol (0.9 g, 3.43 mmole) in tetrahydrofuran (75 mL) and water (7.5 mL) in a sealed tube. Purge the mixture with nitrogen. Add potassium fluoride (400 mg, 6.89 mmole), tris(dibenzylideneacetone)dipalladium (0) (200 mg, 0.22 mmole) and tri-tert-butylphosphonium tetrafluoroborate (200 mg, 0.68 mmole). Seal the reaction in nitrogen and heat at 65-70 C. overnight. Cool the mixture to room temperature, filter to remove inorganic residue. Concentrate the filtrate and dilute it with dichloromethane (120 mL) and water (30 mL). Separate the organic layer and dry it over magnesium sulfate powder. Concentrate it in vacuo to brown oil. Purify the residue by silica gel column chromatography with eluting solvent of 30-65% ethyl acetate in hexane, then with 0-7% methanol in dichloromethane. Concentrate fractions containing the product and co-evaporate with diethyl ether (2×10 mL), acetone (10 mL), acetone and diethyl ether (10 mL each) subsequently. Dry the solid residue to afford the titled compound as an orange powder (0.30 g, 44%). MS (ESI) m/z (M+H)+407.0 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate;bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); In water; tert-butyl alcohol; at 100℃;Inert atmosphere; Sealed tube; | To a sealable tube containing the title compound from Example 22 Step B (0.075 g, 0.300 mmol), the title compound from Example 22 Step D (0.103 g, 0.390 mmol) and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine) dichloropalladium(II) (10.6 mg, 0.015 mmol) was added tert-butanol (3.3 mL). The tube was flushed with nitrogen before the addition of potassium carbonate (0.12 g, 0.90 mmol) and water (0.42 mL). It was flushed again with nitrogen, sealed and heated to 100 C overnight. The reaction was then cooled to room temperature, poured into saturated aqueous sodium chloride solution and extracted with ethyl acetate. The organic extracts were combined, washed with water, dried over sodium sulfate, filtered and concentrated. The resulting residue was diluted with dimethylsulfoxide, passed through a syringe filter and purified by HPLC (CI 8 column, 10 to 100% acetonitrile/water, both 0.1% v/v trifluoroacetic acid) to provide the title compound: LCMS m/z 307.03 [M + H]+; 1H NMR (500 MHz, DMSO) 8 9.38 (s, 1 H), 8.98 (s, 1 H), 8.80 (s, 1 H), 8.51 (s, 1 H), 7.95 - 7.87 (m, 3 H), 3.15 (s, 4 H), 1.55 (s, 6 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In tetrahydrofuran; at 100℃; for 18.0h; | To a solution of 2-chloro-pyrazolo[l,5-a]pyridine (0.200 g, 1.31 mmol) and the title compound from Example 1 Step D (0.414 g, 1.573 mmol) in tetrahydrofuran ( 6.55 mL) were added palladium acetate (0.029 g, 0.131 mmol), 2-dicyclohexylphosphino- 2',6'-dimethoxy-l,l '-biphenyl (0.108 g, 0.262 mmol), and potassium phosphate tribasic (0.835 g, 3.93 mmol). The resulting mixture was heated at 100 C for 18 hours, then diluted with ethyl acetate, filtered, and concentrated under reduced pressure. Purification by flash chromatography on silica gel (0 - 15% ethyl acetate in hexanes) provided the title compound: LCMS m/z 254.02 [M+H]+; 1H NMR (500MHz, CDC13) δ 9.05 (s, 1 H), 8.74 (s, 1 H), 8.49 (d, J= 6.9 Hz, 2 H), 8.40 (s, 1 H), 7.55 (d, J= 6.9 Hz, 2 H), 7.15 (dd, J= 7.6, 7.9 Hz, 1 H), 6.86(s, 1 H), 6.79 (dd, J= 7.1, 6.6Hz, 1 H), 1.68 (s, 6 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In tetrahydrofuran; at 100℃; for 18.0h; | To a solution of the title compound from Example 1 Step D (0.114 g, 0.434 mmol) and the title compound from Example 1 Step B (0.084 g, 0.434 mmol) in tetrahydrofuran (4.34 mL) were added palladium acetate (0.010 g, 0.043 mmol), 2- dicyclohexylphosphino-2',6'-dimethoxy-l,r-biphenyl (0.036 g, 0.087 mmol), and potassium phosphate tribasic (0.277 g, 1.30 mmol). The resulting mixture was heated at 100 C for 18 hours, then filtered and concentrated under reduced pressure. Purification by column chromatography on silica gel (0 - 25 % ethyl acetate in hexanes) provided the title compound: LCMS m/z 293.86 [M + H]+; 1H NMR (500MHz, CDC13) δ 9.16 (s, 1 H), 8.76 (s, 1 H), 8.45 (dd, J= 2.0, 2.0 Hz, 1 H), 7.66 (d, J= 8.8 Hz, 1 H), 7.11 (d, J= 6.9 Hz, 1 H), 6.75 (dd, J = 6.7, 6.7 Hz, 1 H), 2.45 (br s, 1 H), 2.01 - 1.98 (m, 1 H), 1.68 (s, 6 H), 1.01 (d, J= 8.0 Hz, 2 H), 0.50 (d, J= 5.0 Hz, 2 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In tetrahydrofuran; at 100℃; for 18.0h; | To a solution of the title compound from Example 2 Step D (0.1855 g, 0.704 mmol) and the title compound from Example 2 Step B (0.10 g, 0.586 mmol) in tetrahydrofuran (5.86 mL) were added palladium acetate (0.013 g, 0.059 mmol), 2- dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl (0.048 g, 0.117 mmol), and potassium phosphate tribasic (0.373 g, 1.759mmol). The resulting mixture was heated at 100 C for 18 hours. The mixture was then cooled to room temperature, filtered with the aid of ethyl acetate, and concentrated under reduced pressure. Purification by flash chromatography on silica gel (30 - 50% acetone in dichloromethane) provided the title compound.: LCMS m/z 273.99 [M + H]+; Ή NMR (500MHz, CDC13) δ 8.99 (d, J= 1.6 Hz, 1 H), 8.72(d, J= 2.2 Hz, 1 H), 8.39 (t, J= 2.0 Hz, 1 H), 8.10 (t, J= 2.6 Hz, 1 H), 7.96 (s, 1 H), 7.63 (dd, J= 9.9, 4.8 Hz, 1 H), 7.17 - 7.13 (m, 1 H), 2.00 (br s, 1 H), 1.68 (s, 6 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In tetrahydrofuran; at 100℃; for 18.0h; | To a solution of the title compound from Example 2 Step D (0.135 g, 0.514 mmol) and the title compound from Example 3 Step B (0.079 g, 0.428 mmol) in tetrahydrofuran (4.28 mL) were added palladium acetate (9.61 mg, 0.043 mmol), 2- dicyclohexylphosphino-2',6'-dimethoxy-l,l'-biphenyl (0.035 g 0.086 mmol), and potassium phosphate tribasic (0.273 g, 1.284 mmol). The resulting mixture was heated at 100 C for 18 hours, then filtered with the aid of ethyl acetate and concentrated under reduced pressure. Purification by flash chromatography on silica gel (50% acetone in dichloromethane) provided the title compound: LCMS m/z 286.17 [M + H]+; 1H NMR (500MHz, CDC13) δ 8.83 (s, 1 H), 8.75(s, 1 H), 8.26 (d, J= 2.0 Hz, 1 H), 7.85 (s, 1 H), 7.63 (dd, J= 9.8, 5.1 Hz, 1 H), 7.16 - 7.12 (m, 1 H), 2.64 (s, 3 H), 2.28 (br s, 1 H), 1.67 (s, 6 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In tetrahydrofuran; at 100℃; for 18.0h; | To a solution of the title compound from Example 2 Step D (0.053 g, 0.202 mmol) and the title compound from Example 4 Step A (0.033 g, 0.169 mmol) in tetrahydrofuran (0.84 mL) were added palladium acetate (0.0038 g, 0.017 mmol), 2- dicyclohexylphosphino-2',6'-dimethoxy-l,l'-biphenyl (0.014 g, 0.034 mmol), and potassium phosphate tribasic (0.107 g, 0.506 mmol). The resulting mixture was heated at100 C for 18 hours, then filtered with the aid of ethyl acetate and concentrated under reduced pressure. Purification by flash chromatography on silica gel (80% acetone in hexanes) provided the title compound: LCMS m/z 296.96 [M + H]+; 1H NMR (500MHz, CDC13) 6 9.28 (d, J= 1.9Hz, 1 H), 8.87 (d, J=2.0 Hz, 1 H), 8.55 (t, J= 2.1 Hz, 1 H), 8.35 (s, 1 H), 7.79 (dd, J= 9.8, 4.7 Hz, 1 H), 7.45 - 7.41 (m, 1 H), 1.98 (br s, 1 H), 1.69 (s, 6H). |
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