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CAS No. : | 866545-91-7 | MDL No. : | MFCD11616456 |
Formula : | C20H23BN2O4S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NXAUWIGLTZPZKD-UHFFFAOYSA-N |
M.W : | 398.28 | Pubchem ID : | 49758959 |
Synonyms : |
|
Num. heavy atoms : | 28 |
Num. arom. heavy atoms : | 15 |
Fraction Csp3 : | 0.35 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 110.25 |
TPSA : | 78.8 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.0 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 3.84 |
Log Po/w (WLOGP) : | 3.96 |
Log Po/w (MLOGP) : | 2.89 |
Log Po/w (SILICOS-IT) : | 1.72 |
Consensus Log Po/w : | 2.48 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.93 |
Solubility : | 0.00471 mg/ml ; 0.0000118 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -5.19 |
Solubility : | 0.00257 mg/ml ; 0.00000645 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -6.44 |
Solubility : | 0.000146 mg/ml ; 0.000000366 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 3.79 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
99% | With potassium acetate In 1,2-dimethoxyethane at 90℃; for 18 h; Heating / reflux | 3 (850 mg, 0.0024 mol) was dissolved in 20 mL of DME and pinnacol borane (921 mg, 0.0036 mol), Pd2Cl2(dppf)2 (197 mg, 0.24 mmol) and KOAc (713 mg, 0.00726 mol) were added and the mixture was stirred and refluxed at 90°C for 18h. Diluted with ethyl acetate and the organic phase washed with water and brine then dried (Na2SO4) and concentrated in vacuo. The residue was subjected to flash chromatography (20percent EtOAc/80percent hexanes) to give 900 mg (99percent) of the desired product 4. |
79% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In toluene for 24 h; Reflux; Inert atmosphere | (14.01 g, 142.76 mmol) and Pd (dppf) Cl2 (0.87 g, 1.07 mmmol) were added to a solution of intermediate product B (25.0 g, 71.38 mmol), bisphenolacorodiuboron (23.56 g, 92.80 mmol) Was suspended in toluene (300 mL), and the mixture was stirred under reflux for 24 hours under a stream of nitrogen.Extraction is carried out with dichloromethane and distilled water, and the organic layer is subjected to silica gel filtration. The organic solution was removed and hexane:The residue was subjected to silica gel column chromatography with dichloromethane = 6: 4 (v / v) to obtain 22.5 g (yield: 79percent) of the intermediate product (C)Respectively. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81.5% | at 20 - 30℃; Large scale | 3-(4 ,5,5-tetramethyl-l ,2-dioxaborolan-2-yl)-l-tosyl-lH-pyrrolo[2,3-b]pyridine: [00394] Dichloromethane (165.6 kg) and pinacolate alcohol (3.54 kg) was added to a 200L glass-lined reactor. The mixture was stirred until the solid dissolved completely. Then, l-tosyl-lH-pyrrolo[2,3-b]pyridin-3-ylboronic acid (8.65 kg) was added in portions (2 kg every 5 minutes) while maintaining the temperature of about 20-30 °C. After the addition, the temperature was maintained at about 20-30 °C while stirring. The completeness of the reaction was measured by HPLC (method B) with sample aliquots every 60 minutes. The reaction was considered complete when the peak area of 31-tosyl-lH-pyrrolo[2,3-b]pyridin- 3-ylboronic acid was less than 1percent. Typical retention time for 3-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)-l-tosyl-lH-pyrrolo [2,3 -b]pyri dine) was 6.4 minutes. [00395] The mixture was filtered through silica gel (3 kg). The cake was rinsed twice with dichloromethane (15 kg each rinse). The filtrate was combined with the washing liquids, and then concentrated below 30 °C under vacuum at a pressure less than -0.08 MPa until no fraction distilled out. Solvent was continued to be removed by vacuum for 2 hours. Isopropanol (17.2 kg) was added to the residue. The mixture was heated to reflux at about 80-85 °C. The mixture refluxed for 30 minutes until the solid dissolved completely. The mixture was cooled below 35 °C, and then to about 0-10 °C. The mixture crystallized at 0-10 °C for 2 hours and then filtered. After filtration, the resultant cake was dried at about 35-45 °C until the water content detected by KF (Karl Fisher reaction) was less than 0.5percent and the LOD (loss on drying) was less than 0.5percent. An off-white solid resulted (8.8 kg and 99.7percent purity as measured by HPLC analysis (method B), 81.5percent yield of 3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-l-tosyl-lH-pyrrolo[2,3-b]pyridine). |
81.5% | at 20 - 30℃; Large scale | [0278] 3-(4, 4, 5, 5-tetramethyl-l, 3, 2-dioxaborolan-2-yl)-l-tosyl-lH-pyrrolo[2, 3-b Jpyridine: [0279] Dichloromethane (165.6 kg) and pinacolate alcohol (3.54 kg) was added to a 200L glass-lined reactor. The mixture was stirred until the solid dissolved completely. Then, l-tosyl-lH-pyrrolo[2,3-b]pyridin-3-ylboronic acid (8.65 kg) was added in portions (2 kg every 5 minutes) while maintaining the temperature of about 20-30 °C. After the addition, t -rature was maintained at about 20-30 °C while stirring. The completeness of the reaction was measured by HPLC (method B) with sample aliquots every 60 minutes. The reaction was considered complete when the peak area of 3 l-tosyl-lH-pyrrolo[2,3-b]pyridin- 3-ylboronic acid was less than 1percent. Typical retention time for 3-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)-l-tosyl-lH-pyrrolo[2,3-b]pyridine) was 6.4 minutes. [0280] The mixture was filtered through silica gel (3 kg). The cake was rinsed twice with dichloromethane (15 kg each rinse). The filtrate was combined with the washing liquids, and then concentrated below 30 °C under vacuum at a pressure less than -0.08 MPa until no fraction distilled out. Solvent was continued to be removed by vacuum for 2 hours. Isopropanol (17.2 kg) was added to the residue. The mixture was heated to reflux at about 80-85 °C. The mixture refluxed for 30 minutes until the solid dissolved completely. The mixture was cooled below 35 °C, and then to about 0-10 °C. The mixture crystallized at 0-10 °C for 2 hours and then filtered. After filtration, the resultant cake was dried at about 35-45 °C until the water content detected by KF (Karl Fisher reaction) was less than 0.5percent and the LOD (loss on drying) was less than 0.5percent. An off-white solid resulted (8.8 kg and 99.7percent purity as measured by HPLC analysis (method B), 81.5percent yield of |
81.5% | at 20 - 30℃; Large scale | [0400] 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine: [0401] Dichloromethane (165.6 kg) and pinacolate alcohol (3.54 kg) was added to a 200 L glass-lined reactor. The mixture was stirred until the solid dissolved completely. Then, l-tosyl-lH-pyrrolo[2,3-b]pyridin-3-ylboronic acid (8.65 kg) was added in portions (2 kg every 5 minutes) while maintaining the temperature of about 20-30 °C. After the addition, the temperature was maintained at about 20-30 °C while stirring. The completeness of the reaction was measured by HPLC (method B) with sample aliquots every 60 minutes. The reaction was considered complete when the peak area of 31-tosyl-lH-pyrrolo[2,3-b]pyridin- 3-ylboronic acid was less than 1percent. Typical retention time for 3-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)-l-tosyl-lH-pyrrolo[2,3-b]pyridine) was 6.4 minutes. [0402] The mixture was filtered through silica gel (3 kg). The cake was rinsed twice with dichloromethane (15 kg each rinse). The filtrate was combined with the washing liquids, and then concentrated below 30 °C under vacuum at a pressure less than -0.08 MPa until no fraction distilled out. Solvent was continued to be removed by vacuum for 2 hours. Isopropanol (17.2 kg) was added to the residue. The mixture was heated to reflux at about 80-85 °C. The mixture refluxed for 30 minutes until the solid dissolved completely. The mixture was cooled below 35 °C, and then to about 0-10 °C. The mixture crystallized at 0-10 °C for 2 hours and then filtered. After filtration, the resultant cake was dried at about 35-45 °C until the water content detected by KF (Karl Fisher reaction) was less than 0.5percent and the LOD (loss on drying) was less than 0.5percent. An off-white solid resulted (8.8 kg and 99.7percent purity as measured by HPLC analysis (method B), 81.5percent yield of 3-(4,4,5,5-tetramemyl-l,3,2-dioxaborolan-2-yl)-l-tosyl-lH-pyrrolo[2,3-b]pyridine). |
8.8kg | at 20 - 30℃; for 1.08333 h; Large scale | [0390] Example Id: 3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-l-tosyl-lH- pyrrolo[2,3-b]pyridine (la) [0391] Dichloromethane (165.6 kg) and pinacolate alcohol (3.54 kg) were added to a 200 L glass-lined reactor. The mixture was stirred until the solid dissolved completely. Then, l-tosyl-lH-pyrrolo[2,3-b]pyridin-3-ylboronic acid (8a) (8.65 kg) was added in portions (2 kg every 5 minutes) while maintaining the temperature of about 20-30 °C. After the addition, the temperature was maintained at about 20-30 °C while stirring. The completeness of the reaction was measured by HPLC (method B) with sample aliquots every 60 minutes. The reaction was considered complete when the peak area of l-tosyl-lH-pyrrolo[2,3-b]pyridin-3- ylboronic acid (8a) was less than 1percent. [0392] The mixture was filtered through silica gel (3 kg). The cake was rinsed twice with dichloromethane (15 kg each rinse). The filtrate was combined with the washing liquids, and then concentrated below 30 °C under vacuum at a pressure less than -0.08 MPa until no fraction distilled out. Solvent was continued to be removed by vacuum for 2 hours. Isopropanol (17.2 kg) was added to the residue. The mixture was heated to reflux at about 80-85 °C. The mixture refluxed for 30 minutes until the solid dissolved completely. The mixture was cooled below 35 °C, and then to about 0-10 °C. The mixture crystallized at 0-10 °C for 2 hours and was then filtered. After filtration, the resultant cake was dried at about 35- 45 °C until the water content detected by KF (Karl Fisher reaction) was less than 0.5percent and the LOD (loss on drying) was less than 0.5percent. An off-white solid resulted (8.8 kg and 99.7percent purity as measured by HPLC analysis (method B) of 3-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)-l-tosyl-lH-pyrrolo[2,3-b]pyridine (la)). |
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