Home Cart 0 Sign in  
X

[ CAS No. 24244-60-8 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 24244-60-8
Chemical Structure| 24244-60-8
Chemical Structure| 24244-60-8
Structure of 24244-60-8 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 24244-60-8 ]

Related Doc. of [ 24244-60-8 ]

Alternatived Products of [ 24244-60-8 ]

Product Details of [ 24244-60-8 ]

CAS No. :24244-60-8 MDL No. :MFCD09999263
Formula : C11H9NO2S Boiling Point : -
Linear Structure Formula :- InChI Key :MPTVNPMFAZVTJG-UHFFFAOYSA-N
M.W : 219.26 Pubchem ID :289829
Synonyms :

Calculated chemistry of [ 24244-60-8 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 56.18
TPSA : 55.41 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.23 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.48
Log Po/w (XLOGP3) : 1.98
Log Po/w (WLOGP) : 3.0
Log Po/w (MLOGP) : 1.51
Log Po/w (SILICOS-IT) : 1.78
Consensus Log Po/w : 1.95

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.91
Solubility : 0.272 mg/ml ; 0.00124 mol/l
Class : Soluble
Log S (Ali) : -2.77
Solubility : 0.373 mg/ml ; 0.0017 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.47
Solubility : 0.00736 mg/ml ; 0.0000336 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.07

Safety of [ 24244-60-8 ]

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:

Application In Synthesis of [ 24244-60-8 ]

* 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.

  • Downstream synthetic route of [ 24244-60-8 ]

[ 24244-60-8 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 24244-60-8 ]
  • [ 3761-92-0 ]
  • [ 1129-69-7 ]
  • 3
  • [ 24244-60-8 ]
  • [ 30043-41-5 ]
  • [ 71532-23-5 ]
  • 4
  • [ 24244-60-8 ]
  • phenylmagnesium bromide [ No CAS ]
  • [ 1008-89-5 ]
  • 5
  • [ 24244-60-8 ]
  • [ 4294-57-9 ]
  • [ 4467-06-5 ]
  • 6
  • [ 24244-60-8 ]
  • [ 6921-34-2 ]
  • [ 101-82-6 ]
  • 9
  • [ 24244-60-8 ]
  • [ 670-98-4 ]
  • 10
  • [ 24244-60-8 ]
  • [ 581-47-5 ]
YieldReaction ConditionsOperation in experiment
81% Example 1 Synthesis of 2,4'-bipyridine Tetrahydrofuran (10 ml) was charged in a nitrogen-substituted flask having an inner volume of 50 ml, cooled to -78C, and a solution (1.6 M, 10.3 ml, 16.4 mmol) of n-butyllithium in hexane was added. To this solution was added dropwise over 10 min a solution obtained by dissolving 4-bromopyridine (2.59 g, 16.4 mmol) in tetrahydrofuran (3 ml). The reaction mixture was stirred for 1 hr and a solution obtained by dissolving <strong>[24244-60-8]2-benzenesulfonylpyridine</strong> (3.00 g, 13.7 mmol) in tetrahydrofuran (5 ml) was added dropwise over 10 min. The reaction mixture was stirred for 3 hr, and isopropanol (1 ml) was added at the same temperature to stop the reaction. The obtained reaction mixture was added to water, and the mixture was extracted with ethyl acetate (15 ml*2). The extract was concentrated and purified by silica gel chromatography to give the title compound having the following analytical data (1.75 g, yield 81% based on <strong>[24244-60-8]2-benzenesulfonylpyridine</strong>) as a white solid. 1H-NMR spectrum (CDCl3) delta: 7.33-7.37 (m, 1H), 7.80-7.91 (m, 4H), 8.72-8.76 (m, 3H)
  • 11
  • [ 24244-60-8 ]
  • [ 581-50-0 ]
YieldReaction ConditionsOperation in experiment
91% Example 3 Synthesis of 2,3'-bipyridine Tetrahydrofuran (10 ml) and isopropylmagnesium chloride (2.0 M, 8.2 ml, 16.4 mmol) were charged in a nitrogen-substituted flask having an inner volume of 50 ml and then a solution obtained by dissolving 3-bromopyridine (2.59 g, 16.4 mmol) in tetrahydrofuran (3 ml) was added dropwise over 10 min. The reaction mixture was stirred for 1 hr, and a solution obtained by dissolving 2-benzenesulfonylpyridine (3.00 g, 13.7 mmol) in tetrahydrofuran (5 ml) was added dropwise over 10 min. The reaction mixture was stirred at room temperature for 5 hr, and isopropanol (1 ml) was added to stop the reaction. The obtained reaction mixture was added to water, and the mixture was extracted with ethyl acetate (15 ml*2). The extract was concentrated and purified by silica gel chromatography to give the title compound (1.65 g, yield 91% based on 2-benzenesulfonylpyridine) having the following analytical data as a colorless oil. 1H-NMR spectrum (CDCl3) delta: 7.23-7.58 (m, 2H), 7.70-7.91 (m, 2H), 8.33-8.39 (m, 1H), 8.62-8.88 (m, 2H), 9.20 (d, 1H, J=3.0 Hz)
  • 12
  • [ 24244-60-8 ]
  • [ 2433-17-2 ]
YieldReaction ConditionsOperation in experiment
55% Example 9 Synthesis of 2-(2'-thiazolyl)pyridine Tetrahydrofuran (10 ml) was charged in a nitrogen-substituted flask having an inner volume of 50 ml, cooled to -78C, and a solution (1.6 M, 10.3 ml, 16.4 mmol) of n-butyllithium in hexane was added. To this solution was added dropwise over 10 min a solution obtained by dissolving thiazole (1.40 g, 16.4 mmol) in tetrahydrofuran (3 ml). The reaction mixture was stirred for 30 min, and a solution obtained by dissolving <strong>[24244-60-8]2-benzenesulfonylpyridine</strong> (3.00 g, 13.7 mmol) in tetrahydrofuran (5 ml) was added dropwise over 10 min. The reaction mixture was stirred for 3 hr, and isopropanol (1 ml) was added at the same temperature to stop the reaction. The obtained reaction mixture was added to water, and the mixture was extracted with ethyl acetate (15 ml*2). The extract was concentrated and purified by silica gel chromatography to give the title compound having the following analytical data (1.22 g, yield 55% based on <strong>[24244-60-8]2-benzenesulfonylpyridine</strong>) as a pale-yellow solid. 1H-NMR spectrum (CDCl3) delta: 7.28-7.32 (m, 1H), 7.43 (d, 1H, J=3.2 Hz), 7.75-7.80 (m, 1H), 7.91 (d, 1H, J=3.2 Hz), 8.16-8.22 (m, 1H), 8.58-8.62 (m, 1H)
  • 13
  • [ 24244-60-8 ]
  • [ 55484-03-2 ]
YieldReaction ConditionsOperation in experiment
73% Example 6 Synthesis of 2-(2'-furyl)pyridine Tetrahydrofuran (10 ml) was charged in a nitrogen-substituted flask having an inner volume of 50 ml, cooled to -78C, and a solution (1.6 M, 10.3 ml, 16.4 mmol) of n-butyllithium in hexane was added. To this solution was added dropwise over 10 min a solution obtained by dissolving 2-bromofuran (2.38 g, 16.4 mmol) in tetrahydrofuran (3 ml). The reaction mixture was stirred for 30 min, and a solution obtained by dissolving <strong>[24244-60-8]2-benzenesulfonylpyridine</strong> (3.00 g, 13.7 mmol) in tetrahydrofuran (5 ml) was added dropwise over 10 min. The reaction mixture was stirred for 3 hr, and isopropanol (1 ml) was added at the same temperature to stop the reaction. The obtained reaction mixture was added to water, and the mixture was extracted with ethyl acetate (15 ml*2). The extract was concentrated and purified by silica gel chromatography to give the title compound (1.45 g, yield 73% based on <strong>[24244-60-8]2-benzenesulfonylpyridine</strong>) having the following analytical data as a colorless oil. 1H-NMR spectrum (CDCl3) d: 6.50-6.63 (m, 1H), 6.84-7.23 (m, 2H), 7.50-7.83 (m, 3H), 8.58-8.73 (m, 1H)
  • 14
  • [ 24244-60-8 ]
  • [ 152191-21-4 ]
YieldReaction ConditionsOperation in experiment
71% Example 10 Synthesis of 1-benzenesulfonyl-2-(4-methyl-2-pyridyl)indole Tetrahydrofuran (10 ml) was charged in a nitrogen-substituted flask having an inner volume of 50 ml, cooled to -78C, and a solution (1.6 M, 10.3 ml, 16.4 mmol) of n-butyllithium in hexane was added. To this solution was added dropwise over 10 min a solution obtained by dissolving 1-benzenesulfonylindole (4.22 g, 16.4 mmol) in tetrahydrofuran (7 ml). The reaction mixture was stirred for 30 min, and a solution obtained by dissolving 4-methyl-<strong>[24244-60-8]2-benzenesulfonylpyridine</strong> (3.00 g, 12.9 mmol) in tetrahydrofuran (5 ml) was added dropwise over 10 min. The reaction mixture was stirred for 3 hr, and isopropanol (1 ml) was added at the same temperature to stop the reaction. The obtained reaction mixture was added to water, and the mixture was extracted with ethyl acetate (15 ml*2). The extract was concentrated and purified by silica gel chromatography to give the title compound having the following analytical data (3.25 g, yield 71% based on 4-methyl-<strong>[24244-60-8]2-benzenesulfonylpyridine</strong>) as a pale-yellow solid. 1H-NMR spectrum (CDCl3) delta: 2.47 (s, 3H), 6.85 (s, 1H), 7.17 (d, 1H, J=5.0 Hz), 7.19-7.33 (m, 5H), 7.47 (d, 1H, J=7.4 Hz), 7.56 (s, 1H), 7.64-7.68 (m, 2H), 8.18 (d, 1H, J=8.0 Hz), 8.60 (d, 1H, J=5.2 Hz)
  • 15
  • [ 24244-60-8 ]
  • [ 21298-55-5 ]
YieldReaction ConditionsOperation in experiment
83% Example 5 Synthesis of 2-(3'-thienyl)pyridine Tetrahydrofuran (10ml) was charged in a nitrogen-substituted flask having an inner volume of 50 ml, cooled to -78C, and a solution (1.6 M, 10.3 ml, 16.4 mmol) of n-butyllithium in hexane was added. To this solution was added dropwise over 10 min a solution obtained by dissolving 3-bromothiophene (2.67 g, 16.4 mmol) in tetrahydrofuran (3 ml). The reaction mixture was stirred for 30 min, and a solution obtained by dissolving <strong>[24244-60-8]2-benzenesulfonylpyridine</strong> (3.00 g, 13.7 mmol) in tetrahydrofuran (5 ml) was added dropwise over 10 min. The reaction mixture was stirred for 3 hr, and isopropanol (1 ml) was added at the same temperature to stop the reaction. The obtained reaction mixture was added to water, and the mixture was extracted with ethyl acetate (15 ml*2). The extract was concentrated and purified by silica gel chromatography to give the title compound (1.83 g, yield 83% based on <strong>[24244-60-8]2-benzenesulfonylpyridine</strong>) having the following analytical data as a colorless oil. 1H-NMR spectrum (CDCl3) delta: 7.14-7.19 (m, 1H), 7.39 (dd, 1H, J=3.2 Hz, 5.0 Hz), 7.60-7.73 (m, 3H), 7.90 (dd, 1H, J=0.8 Hz, 3.2 Hz), 8.60-8.63 (m, 1H)
  • 16
  • [ 24244-60-8 ]
  • 2-(1'-benzyloxy-5'-pyrazolyl)pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% Example 7 Synthesis of 2-(1'-benzyloxy-5'-pyrazolyl)pyridine Tetrahydrofuran (10 ml) was charged in a nitrogen-substituted flask having an inner volume of 50 ml, cooled to -78C, and a solution (1.6 M, 10.3 ml, 16.4 mmol) of n-butyllithium in hexane was added. To this solution was added dropwise over 10 min a solution obtained by dissolving 1-benzyloxypyrazole (2.86 g, 16.4 mmol) in tetrahydrofuran (3 ml). The reaction mixture was stirred for 30 min, and a solution obtained by dissolving <strong>[24244-60-8]2-benzenesulfonylpyridine</strong> (3.00 g, 13.7 mmol) in tetrahydrofuran (5 ml) was added dropwise over 10 min. The reaction mixture was stirred for 3 hr, and isopropanol (1 ml) was added at the same temperature to stop the reaction. The obtained reaction mixture was added to water, and the mixture was extracted with ethyl acetate (15 ml*2). The extract was concentrated and purified by silica gel chromatography to give the title compound (2.90 g, yield 84% based on <strong>[24244-60-8]2-benzenesulfonylpyridine</strong>) having the following analytical data as a white solid. 1H-NMR spectrum (CDCl3) delta: 5.30 (s, 2H), 6.68 (d, 1H, J=2.4 Hz)), 7.19-7.18 (m, 6H), 7.37 (d, 1H, J=2.4 Hz), 7.64-7.77 (m, 2H), 8.62 (dd, 1H, J=1.8 Hz, 4.8 Hz)
  • 17
  • [ 24244-60-8 ]
  • [ 90417-11-1 ]
YieldReaction ConditionsOperation in experiment
69% Example 8 Synthesis of 2-(4'-methyl-2'-oxazolyl)pyridine Tetrahydrofuran (10 ml) was charged in a nitrogen-substituted flask having an inner volume of 50 ml, cooled to -78C, and a solution (1.6 M, 10.3 ml, 16.4 mmol) of n-butyllithium in hexane was added. To this solution was added dropwise over 10 min a solution obtained by dissolving 4-methyloxazole (1.36 g, 16.4 mmol) in tetrahydrofuran (3 ml). The reaction mixture was stirred for 30 min, and a solution obtained by dissolving <strong>[24244-60-8]2-benzenesulfonylpyridine</strong> (3.00 g, 13.7 mmol) in tetrahydrofuran (5 ml) was added dropwise over 10 min. The reaction mixture was stirred for 3 hr, and isopropanol (1 ml) was added at the same temperature to stop the reaction. The obtained reaction mixture was added to water, and the mixture was extracted with ethyl acetate (15 ml*2). The extract was concentrated and purified by silica gel chromatography to give the title compound having the following analytical data (1.51 g, yield 69% based on <strong>[24244-60-8]2-benzenesulfonylpyridine</strong>) as a white solid. 1H-NMR spectrum (CDCl3) delta: 2.29 (d, 3H, J=1.6 Hz), 7.39-7.45 (m, 1H), 7.62 (q, 1H, J=1.6 Hz), 7.86-7.92 (m, 1H), 8.17-8.23 (m, 1H), 8.82-8.86 (m, 1H)
  • 18
  • [ 24244-60-8 ]
  • [ 35299-70-8 ]
YieldReaction ConditionsOperation in experiment
78% Example 4 Synthesis of 6-chloro-2-(2'-thienyl)pyridine Tetrahydrofuran (15 ml) and magnesium (480 mg, 19.7 mmol) were charged in a nitrogen-substituted flask having an inner volume of 50 ml, and then a solution obtained by dissolving 2-bromothiophene (2.67 g, 16.4 mmol) in tetrahydrofuran (3 ml) was added dropwise over 10 min. The reaction mixture was stirred for 1 hr, and a solution obtained by dissolving 6-chloro-<strong>[24244-60-8]2-benzenesulfonylpyridine</strong> (3.00 g, 13.7 mmol) in tetrahydrofuran (5 ml) was added dropwise over 10 min. The reaction mixture was stirred at room temperature for 5 hr, and isopropanol (1 ml) was added to stop the reaction. The obtained reaction mixture was added to water, and the mixture was extracted with ethyl acetate (15 ml*2). The extract was concentrated and purified by silica gel chromatography to give the title compound (1.72 g, yield 78% based on 6-chloro-<strong>[24244-60-8]2-benzenesulfonylpyridine</strong>) having the following analytical data as a colorless oil. 1H-NMR spectrum (CDCl3) delta: 7.12-7.17 (m, 2H), 7.47-7.55 (m, 2H), 7.62-7.74 (m, 2H)
  • 19
  • [ 24244-60-8 ]
  • [ 381725-49-1 ]
YieldReaction ConditionsOperation in experiment
95% Tetrahydrofuran (230 kg) was charged in a reactor vessel (inner volume 1000 L) and cooled to -76C, after which a solution (15.2 wt%, 118 kg, 278 mol) of n-butyllithium in hexane was added therein. To this solution was added dropwise a solution obtained by dissolving 5-bromo-2-methoxypyridine (47.0 kg, 250 mol) in tetrahydrofuran (71 kg) over 3.5 hr at an inside temperature of -71C to -75C. After the completion of the dropwise addition, the mixture was stirred for 1 hr and a sample was taken to confirm the disappearance of 5-bromo-2-methoxypyridine. To the obtained reaction mixture was added dropwise a solution obtained by dissolving <strong>[24244-60-8]2-benzenesulfonylpyridine</strong> (45.7 kg, 209 mol) in tetrahydrofuran (133 kg) at a temperature range of -71C to -75C over 6.5 hr. After the completion of the dropwise addition, the mixture was stirred at -71C for 3 hr and isopropanol (32 kg) was added to stop the reaction. The obtained reaction mixture was warmed to 0C and the reaction mixture was transferred to an extraction vessel containing water (216 kg) while keeping the inside temperature of the extraction vessel from exceeding 20C. After the completion of the transfer, the mixture was stirred for 30 min, stood still and the organic layer was separated. The aqueous layer was extracted twice with ethyl acetate (82 kg + 86 kg) and the extracts and the above-mentioned organic layer were combined and concentrated under reduced pressure to give a crude product (gross: 52.8 kg).
  • 20
  • crotonaldehyde (2-butenal) [ No CAS ]
  • [ 24224-99-5 ]
  • [ 24244-60-8 ]
YieldReaction ConditionsOperation in experiment
99% With lithium perchlorate; In toluene; butan-1-ol; Example 1 First, 8.05 g (113 mmol) of crotonaldehyde (2-butenal) and 9.17 g (54.9 mmol) of benzenesulfonyl cyanide were introduced to a 3-necked flask (50 ml volume) equipped with a thermometer, a magnetic stirrer, a Dean-Stark water type distilling receiver, and a condenser tube. Toluene (15 ml) as a solvent and butanol (1.5 ml) were added, and then 589 mg (5.55 mmol) of lithium perchlorate was added. Next, the mixture was heated under reflux for 15 hours while agitating at an internal temperature of 110 C. in a nitrogen atmosphere, and separating and removing water that was produced. After this solution was cooled to room temperature, the low-boiling components, such as solvent, etc., were removed under reduced pressure and the resulting concentrate was cooled in an ice bath to precipitate crystals. The crystals were filtered with a glass filter and washed with 10 ml of toluene that had been cooled to 5 C. or lower. Then the crystal were dried for 2 hours in vacuo to give 10.8 g of 2-benzenesulfonylpyridine having the following properties as colorless crystals (purity of 99%, yield of 89% based on benzenesulfonyl cyanide).
  • 21
  • [ 123-73-9 ]
  • [ 24224-99-5 ]
  • [ 24244-60-8 ]
YieldReaction ConditionsOperation in experiment
98% With sodium perchlorate; In toluene; butan-1-ol; Example 3 First, 8.22 g (115 mmol) of crotonaldehyde and 9.22 g (55.2 mmol) of benzenesulfonyl cyanide were introduced to the same reaction vessel as in Example 1. Toluene (15 ml) as the solvemnt and butanol (1.5 ml) were added, and 677 mg (5.55 mmol) of sodium perchlorate was added. Then the mixture was heated under reflux for 18 hours while agitating at an internal temperature of 110 C. in a nitrogen atmosphere, separating and removing water that was produced. After this solution was cooled to room temperature, the low-boiling components, such as solvent, etc., were removed under reduced pressure and the resulting concentrate was cooled in an ice bath to precipitate crystals. The crystals were filtered with a glass filter and washed with 10 ml of toluene that had been cooled to 5 C. or lower. Then the crystals were dried for 2 hours in vacuo to give 11.2 g of 2-benzenesulfonylpyridine as colorless crystals (purity of 98%, yield of 91% based on benzenesulfonyl cyanide).
90% In toluene; Example 4 First, 10.16 g (145 mmol) of crotonaldehyde and 10.09 g (60.4 mmol) of benzenesulfonyl cyanide were introduced to the same reaction vessel as in Example 1. Toluene (15 ml) were added as the solvent, and the mixture was heated under reflux for 15 hours while agitating at an internal temperature of 110 C. in a nitrogen atmosphere, separating and removing water that was produced. After this solution was cooled to room temperature, the low-boiling components, such as solvent, etc., were removed under reduced pressure and the resulting concentrate was cooled in an ice bath to precipitate crystals. The crystals were filtered with a glass filter and washed with 10 ml of toluene that had been cooled to 5 C. or lower. Then the crystals were dried in vacuo for 2 hours to give 9.11 g of 2-benzenesulfonyl-pyridine as colorless crystals (purity of 90%, yield of 62% based on benzenesulfonyl cyanide).
  • 22
  • [ 123-73-9 ]
  • [ 126-73-8 ]
  • [ 24224-99-5 ]
  • [ 24244-60-8 ]
YieldReaction ConditionsOperation in experiment
99% In toluene; butan-1-ol; Example 9 First, 8.07 g (113 mmol) of crotonaldehyde and 9.69 g (58.0 mmol) of benzenesulfonyl cyanide were introduced to the same reaction vessel as in Example 1. Toluene (15 ml) as the solvent and butanol (1.5 ml) were added, and 1.45 g (5.80 mmol) of tributyl phosphate was added. Then the mixture was heated under reflux for 4 hours while agitating at an internal temperature of 116 C. in a nitrogen atmosphere, separating and removing water that was produced. After this solution was cooled to room temperature, the low-boiling components, such as solvent, etc., were removed under reduced pressure and the resulting concentrate was cooled in an ice bath to precipitate crystals. The crystals were filtered with a glass filter and washed with 10 ml of toluene that had been cooled to 5 C. or lower. Then the crystals were dried for 2 hours in vacuo to give 11.3 g of 2-benzenesulfonylpyridine as colorless crystals (purity of 99%, yield of 88% based on benzenesulfonyl cyanide).
  • 23
  • [ 123-73-9 ]
  • [ 688-74-4 ]
  • [ 24224-99-5 ]
  • [ 24244-60-8 ]
YieldReaction ConditionsOperation in experiment
99% In di-isopropyl ether; butan-1-ol; Example 7 First, 8.20 g (115 mmol) of crotonaldehyde and 9.55 g (57.2 mmol) of benzenesulfonyl cyanide were introduced to the same reaction vessel as in Example 1. Diisopropyl ether (15 ml) as the solvent and butanol (1.5 ml) were added, and 1.33 g (5.78 mmol) of tributyl borate was added. Then the mixture was heated under reflux for 20 hours while agitating at an internal temperature of 83 C. in a nitrogen atmosphere, separating and removing water that was produced. After this solution was cooled to room temperature, the low-boiling components, such as solvent, etc., were removed under reduced pressure, and the resulting concentrate was cooled in an ice bath to precipitate crystals. The crystals were filtered with a glass filter and washed with 10 ml of isopropyl ether that had been cooled to 5 C. or lower. Then the crystals were dried for 2 hours in vacuo to give 11.9 g of 2-benzenesulfonylpyridine as colorless crystals (purity of 99%, yield of 94% based on benzenesulfonyl cyanide).
99% In toluene; butan-1-ol; Example 6 First, 8.20 g (115 mmol) of crotonaldehyde and 9.55 g (57.2 mmol) of benzenesulfonyl cyanide were introduced to the same reaction vessel as in Example 1. Toluene (15 ml) as the solvent and butanol (1.5 ml) were added, and 1.33 g (5.78 mmol) of tributyl borate was added. Then the mixture was heated under reflux for 3 hours while agitating at an internal temperature of 110 C. in a nitrogen atmosphere, separating and removing water that was produced. After this solution was cooled to room temperature, the low-boiling components, such as solvent, etc., were removed under reduced pressure and the resulting concentrate was cooled in an ice bath to precipitate crystals. The crystals were filtered with a glass filter and washed with 10 ml of toluene that had been cooled to 5 C. or lower. Then the crystals were dried for 2 hours in vacuo to give 11.3 g of 2-benzenesulfonylpyridine as colorless crystals (purity of 99%, yield of 89% based on benzenesulfonyl cyanide).
98% In toluene; Example 2 First, 8.20 g (115 mmol) of crotonaldehyde and 9.55 g (57.2 mmol) of benzenesulfonyl cyanide were introduced to the same reaction vessel as in Example 1. Toluene (15 ml) was added as the solvent, and 1.33 g (5.78 mmol) of tributyl borate was added. Then the mixture was heated under reflux for 3 hours while agitating at an internal temperature of 110 C. in a nitrogen atmosphere, separating and removing water that was produced. After this solution was cooled to room temperature, the low-boiling components, such as solvent, etc., were removed under reduced pressure and the resulting concentrate was cooled in an ice bath to precipitate crystals. The crystals were filtered with a glass filter and washed with 10 ml of toluene that had been cooled to 5 C. or lower. Then the crystals were dried for 2 hours in vacuo to give 10.9 g of 2-benzenesulfonylpyridine as colorless crystals (purity of 98%, yield of 85% based on benzenesulfonyl cyanide).
  • 24
  • [ 24244-60-8 ]
  • [ 89-98-5 ]
  • [ 1035920-14-9 ]
YieldReaction ConditionsOperation in experiment
Preparation 1-E (2-phenylsulfonyl-pyridin-3-yl)- (2-chlorophenyl) methanone; To n-butyllithium (2.5 N in hexanes; 28 mL), which has been cooled to-65 C, add diisopropylamine while keeping the temperature between-65 and-52 C. A precipitation occurs. Add THF (42 mL) to the lithium diisopropylamine (LDA) suspension. To the suspension, add a solution of 2-phenylsulfonyl pyridine (14 g) in THF (42 mL) while maintaining the temperature between-65 and-55 C. Stir for approximately 15 min. A yellow to orange precipitate forms. Add a solution of 2- chlorobenzaldehyde (8.96 g) in THF (11 mL) to the suspension while keeping the temperature of the reaction mixture between-75 and-60 C during the addition. A red solution is obtained. Stir the reaction mixture for 1 h at-70 C, then warm the reaction mixture to-30 C, followed by a careful addition of 3N HC1 (112 mL). The temperature is allowed to reach 0C at the end of the addition. Warm the reaction mixture to approximately 20 C and extract with toluene (2 x 140mL). Combine the organic layers, wash with water (100 mL) and concentrate to dryness under reduced pressure to yield a yellow solidifying oil. Dissolve the residue in CH2C12 (150 mL) and add a 10 % KBr solution in water (44 mL) and 2,2, 6,6- tetramethylpiperidin-l-oxyl (TEMPO) (728 mg). Cool the reaction mixture to 10 C with an ice bath. Add a solution of 4 % NaOCI (728 mL) and NaHC03 (6.5 g) under vigorous stirring and maintain the temperature around 10 C during the addition. At the end of the addition, warm the reaction mixture to 20C and stir for 1 hour. The organic layer is decanted, separated and concentrated under vacuum to yield 25g of crude oil. Dissolve the oily residue in DMF (100 mL) and slowly add water (160 mL) to precipitate the title compound. Stir the suspension for 1 hour at room temperature, then 15 minutes at 0 C. Filter the suspension, wash the precipitate with DMF/H20, and dry under vacuum at 50C to yield the title compound as a white to off-white solid.'H NMR (600 MHz, CHLOROFORM-d) 8 ppm 7.38 (td, J=7. 52,1. 28 Hz, 1 H) 7.47 (dd, J=7. 80,1. 30 Hz, 1 H) 7.51 (td, J=7. 79,1. 60 Hz, 1 H) 7.51 (t, J=7. 89 Hz, 2 H) 7.50-7. 54 (m, J=7. 75,4. 63 Hz, 1 H) 7.60 (t, J=7. 43 Hz, 1 H) 7.73 (dd, J=7. 75,1. 60 Hz, 1 H) 7.81 (dd, J=7. 79,1. 56 Hz, 1 H) 8.00 (dd, J=8. 44,1. 10 Hz, 2 H) 8.76 (dd, J=4. 63,1. 61 Hz, 1 H).
Preparation 1-C(2-phenylsulfonyl-pyridin-3-yl)-(2-chlorophenyl)methanoneA solution of 1.3 eq of diisopropylamine (based on <strong>[24244-60-8]2-benzenesulfonyl pyridine</strong>) in 5 volumes of THF in a mechanically stirred 3 -necked flask is cooled to -70 to -75 0C. To this solution is added 1.05 eq of w-butyllithium (1.6M in hexanes) at such a rate as to maintain the temperature below -6O0C. The light yellow solution is stirred at -60 to -70 0C for 30 minutes. Once the temperature has cooled back down to - 60 to -650C, 1.0 eq of <strong>[24244-60-8]2-benzene-sulfonyl pyridine</strong>, as a solution in 3 volumes of THF, is added at the fastest rate that will maintain the reaction temperature under -6O0C. A yellow suspension forms during the addition that becomes yellow-orange upon longer stirring. This mixture is stirred for 3 hours at -60 to - 750C, and then 1.06 eq of 2-chlorobenzaldehyde, as a solution in 1 volume of THF, is added dropwise at a <n="9"/>sufficient rate to keep the temperature under -55 0C. The suspension gradually turns orange-red, thins out, and then becomes a clear red solution. The reaction mixture is allowed to stir at -60 to -7O0C for 1 hour, 3N aqueous HCl (7 volumes) is added over 20-30 minutes, and the temperature is allowed to exotherm to 0-100C. The color largely disappears, leaving a biphasic yellow solution. The solution is warmed to at least 1O0C, the layers are separated, and the aqueous layer is back-extracted with 10 volumes of ethyl acetate. The combined organic layers are washed with 10 volumes of saturated sodium bicarbonate solution and concentrated to about 2 volumes. Ethyl acetate (10 volumes) is added, and the solution is once again concentrated to 2 volumes. The thick solution is allowed to stand overnight and is taken to the next step with no purification of the crude alcohol intermediate. The crude alcohol intermediate is transferred to a 3 -necked flask with enough ethyl acetate to make the total solution about 10 volumes. The yellow solution is treated with 3.2 volumes of 10% aqueous (w/w) potassium bromide, followed by 0.07 eq of 2,2,6,6-Tetramethylpiperidine-N-oxide (TEMPO). The orange mixture is cooled to 0-50C and treated with a solution of 1.25 eq of sodium bicarbonate in 12% w/w sodium hypochlorite (9 volumes) and 5 volumes of water over 30-60 minutes while allowing the temperature to exotherm to a maximum of 2O0C. The mixture turns dark brown during the addition, but becomes yellow, and a thick precipitate forms. The biphasic light yellow mixture is allowed to stir at ambient temperature for 1-3 hours, at which time the reaction is generally completed. The biphasic mixture is cooled to 0-50C and stirred for 3 hours at that temperature. The solid is filtered off, washed with 4 volumes of cold ethyl acetate, followed by 4 volumes of water, and dried in vacuo at 450C to constant weight. Typical yield is 80-83% with a purity of greater than 98%. 1H NMR (600 MHz, CDCl3-^) delta ppm 7.38 (td, ./=7.52, 1.28 Hz, 1 H) 7.47 (dd, ./=7.80, 1.30 Hz, 1 H) 7.51 (td, ./=7.79, 1.60 Hz, 1 H) 7.51 (t, ./=7.89 Hz, 2 H) 7.50 - 7.54 (m, J=7.75, 4.63 Hz, 1 H) 7.60 (t, J=7.43 Hz, 1 H) 7.73 (dd, J=7.75, 1.60 Hz, 1 H) 7.81 (dd, J=7.79, 1.56 Hz, 1 H) 8.00 (dd, ./=8.44, 1.10 Hz, 2 H) 8.76 (dd, ./=4.63, 1.61 Hz, 1 H).
  • 25
  • [ 3111-54-4 ]
  • [ 24244-60-8 ]
YieldReaction ConditionsOperation in experiment
Preparation 1-E 2-benzene-sulfonyl pyridine Charge 2-chloropyridine (75 mL, 790 mmol), thiophenol (90 mL, 852 mmol), and DMF (450 mL) to a 2L flask. Add K2CO3 (134.6 g, 962 mmol), then heat to HO0C and stir for 18 hours. Filter the mixture, then rinse the waste cake with DMF (195 mL). The combined crude sulfide solution and rinses are transferred to a 5-L flask, and the waste filtercake is discarded. Glacial acetic acid (57 mL, 995 mmol) is added to the filtrate, then the solution is heated to 4O0C, and 13 wt % NaOCl solution (850 mL, 1.7 mol) is added over 2 hours. After the reaction is complete, water (150 mL) is added, then the pH of the mixture adjusted to 9 with 20 % (w/v) NaOH solution (250 mL). The resulting slurry is cooled to <5 0C, stirred for 1.5 h, then filtered, and the cake washed with water (3 x 200 mL). The product wetcake is dried in a 550C vacuum oven to provide 2-benzene-sulfonyl pyridine (149 g, 676 mmol) in 86 % yield: 1H NMR (500 MHz, CDCl3) delta 8.66 (d, J = 5.5 Hz, IH), 8.19 (d, J = 1.1 Hz, IH), 8.05 (m, 2H), 7.92 (ddd, J= 9.3, 7.7, 1.6 Hz, IH), 7.60 (m, IH), 7.54 (m, 2H), 7.44 (m, IH); IR (KBr) 788, 984, 1124, 1166, 1306, 1424, 1446, 1575, 3085 cm"1; MS (TOF) mlz 220.0439 (220.0427 calcd for C11H10NO2S, MH); Anal, calcd for C11H9NO2S: C, 60.26; H, 4.14; N, 6.39; S, 14.62. Found: C, 60.40; H, 4.02; N, 6.40; S, 14.76.
  • 26
  • [ 24244-60-8 ]
  • [ 104-88-1 ]
  • C18H14ClNO3S [ No CAS ]
  • 27
  • [ 24244-60-8 ]
  • [ 89-98-5 ]
  • [ 1242296-07-6 ]
  • 28
  • [ 24244-60-8 ]
  • [ 89-98-5 ]
  • [ 1035920-14-9 ]
  • C25H19Cl2NO4S [ No CAS ]
  • 29
  • [ 24244-60-8 ]
  • [ 587-04-2 ]
  • [ 1242296-08-7 ]
  • 30
  • [ 24244-60-8 ]
  • [ 587-04-2 ]
  • C18H14ClNO3S [ No CAS ]
  • 31
  • [ 109-04-6 ]
  • [ 24244-60-8 ]
  • 32
  • [ 109-09-1 ]
  • [ 873-55-2 ]
  • [ 24244-60-8 ]
YieldReaction ConditionsOperation in experiment
90% With acetic acid; at 95℃; for 24h;Inert atmosphere; 2-Chloropyridine 2a (1.135 g, 10.0 mmol) is added to 5 mL of HOAc under an argon atmosphere. Phenyl sulfinic sodium salt (2.477 g, 15.0 mmol) is then added. The resulting reaction mixture is stirred at 95 C for 24 h. After the completion of the reaction, the mixture is cooled down, water is added (10 ml) and the mixture is extracted with MeTHF (50 ml). The organic layer is washed with NaHC03 solution (10 ml) once and concentrated. 3a is purified on silica gel and eluted with 50% hexanes/EtOAc to yield 2.0g (90% yield) of white solid after removing the solvent. 1H NMR (400 MHz, CDC13) delta 8.67 (d, / = 4.8 Hz, 1H), 8.21 (d, / = 7.9 Hz, 1H), 8.08 (m, 2H), 7.95 (dt, / = 7.8, 1.7 Hz, 1H), 7.60 (m, 1H), 7.55 (m, 2H), 7.48 (ddd, J = 7.6, 4.7, 1.0 Hz, 1H); 13C NMR (100 MHz, CDC13) delta 158.8, 150.5, 138.9, 138.1, 133.8, 129.1, 128.9, 126.9, 122.2.
73% In water; acetic acid; at 90℃;Large scale; Benzensulfinic sodium salt (21.6 Kg, 131.6 mol) is charged to a reactor and treated with 60 L of a solution of acetic acid and water (3: 1 vol:vol). The contents of the reactor are mixed and treated with 2-chloropyridine (30.0Kg, 264.2 mol). The contents of the reactor are heated to 90C and mixed for 2hrs. An additional solution of benzensulfinic sodium salt (26 Kg, 158.4 mol) in 60 L of acetic acid/water (3: 1 vol:vol) is added to the reactor slowly over 5 hours while maintaining the contents of the reactor at 90C. The contents of the reactor are mixed at 90C for about 8 hours, cooled to 20C, and treated with water (150 L). The contents of the reactor are stirred for 30 minutes and filtered through a centrifuge filter. The filter cake is collected, treated with isopropanol (41.4 Kg, 52.4 L), and stirred at 60C. After 30 minutes the mixture is cooled to 10C over 2 hours, and further mixed for 1 hour at 10C. The mixture is filtered and the filter cake is washed with isopropanol (23.70 Kg, 30 L). The filter cake is collected and dried overnight at 50C to provide 2- (phenylsulfonyl)pyridine. Yield: 42.5Kg, 194 mol; 73%.
  • 33
  • [ 24244-60-8 ]
  • [ 42872-79-7 ]
  • [ 100-39-0 ]
  • [ 1423122-99-9 ]
YieldReaction ConditionsOperation in experiment
75% A reactor containing 3-iodo-4-methylbenzonitrile (3.49 Kg; 14.4 mol) and <strong>[24244-60-8]2-(phenylsulfonyl)pyridine</strong> (3.0 Kg, 13.7 mol) is purged with nitrogen. The reactor is then charged with dimethylformamide (17.38 L), stirred at room temperature for 30 minutes, then cooled to 10C. The contents of the reactor are treated drop- wise with 1 M solution of NaHMDS (sodium hexamethyldisilazane) in tetrahydrofuran (27.4 liters) over 2 hours while keeping the internal temperature below 20C. The reaction mixture is then treated with acetic acid (783 mL) while keeping the internal temperature below 20C. The reaction mixture is heated to 80C and the THF is removed by distillation. The contents of the reactor are then cooled to 25C, treated with water (13.69 L) over 30 minutes, treated with methyl-tetrahydrofuran (MeTHF) (27.3 L), and stirred for 15 minute. The resulting organic phase is collected, washed with water (2 x 6.85 L), and concentrated to a minimum stirrable volume. The concentrated mixture is then treated with acetonitrile (27.4 L) and concentrated under reduced pressure to minimum stirrable volume. The acetonitrile treatment and concentration is repeated twice. The resulting concentrated mixture is then treated with dry acetonitrile (8.75 L) and benzylbromide (2.57Kg, 15.5 mol), heated to 80C, mixed for about 18 hours, and cooled to 25C. The mixture is treated with MeTHF (8.75L), stirred for about 1 hour, and filtered. The resulting filter cake is rinsed with MeTHF and dried for about 18 hours at ~ 50C to provide 1-benzyl-2-(3-iodo-4-cyano- phenyl)methyl)pyridinium bromide. Yield: 5.05 Kg, 10.28 mol; 75%.
  • 34
  • [ 24244-60-8 ]
  • [ 1423123-02-7 ]
  • 35
  • [ 24244-60-8 ]
  • [ 1423123-03-8 ]
  • 36
  • [ 24244-60-8 ]
  • (4aR,9aS)-2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridine-6-carbonitrile hemi-(D)-O,O'-dibenzoyltartaric acid salt [ No CAS ]
  • 37
  • [ 24244-60-8 ]
  • [ 1303515-32-3 ]
  • 38
  • [ 24244-60-8 ]
  • [ 1303515-33-4 ]
  • 41
  • [ 66003-76-7 ]
  • [ 24367-66-6 ]
  • [ 24244-60-8 ]
  • 42
  • [ 109-09-1 ]
  • [ 108-98-5 ]
  • [ 24244-60-8 ]
  • 43
  • [ 24244-60-8 ]
  • [ 1542796-07-5 ]
  • 44
  • [ 24244-60-8 ]
  • [ 1542796-11-1 ]
  • 45
  • [ 24244-60-8 ]
  • [ 1542796-14-4 ]
  • 46
  • [ 24244-60-8 ]
  • [ 1215081-21-2 ]
  • [ 1542795-81-2 ]
YieldReaction ConditionsOperation in experiment
91% With lithium diisopropyl amide; In tetrahydrofuran; ethylbenzene; at -78 - 20℃;Inert atmosphere; Intermediate la (1.0 g, 4.163 mmol) and pyridine sulfone 3a (0.913 g, 4.163 mmol) are dissolved in 10 ml of anhydrous THF under argon. The mixture is cooled to - 78 C with a dry ice/acetone bath. The stirred solution is treated with drop-wise with 2.64 mL (12.5 mmol) of LDA (2.0 M in THF/ethylbenzene). The internal temperature is maintained under -70 C for an additional hour. Upon completion, the reaction is quenched with MeOH at -78 C. The mixture is warmed to room temperature and stirred for an additional 2 h. The reaction mixture should be basic at PH > 12. Aqueous NaOH (30 wt%) is added if necessary. The mixture is then concentrated down to a minimal volume. Water and CH2C12 is added to dilute the mixture. The organic layer is further extracted with CH2C12 and dried with anhydrous Na2S04. The CH2C12 solution is concentrated and compound 5a is purified on silica gel with 5% MeOH in CH2C12 to yield 1.2 g of white solid after dryness, 91% yield; mp 186.1-188.5 C. 1H NMR (400 MHz, CDC13) delta 8.58 (d, J = 4.1 Hz, 1H), 7.68 (dt, / = 7.7, 1.7 Hz, 1H), 7.45 (t, / = 8.3 Hz, 1H), 7.40 (dd, 7 = 8.0, 0.5 Hz, 1H), 7.21 (t, J = 6.2 Hz, 1H), 6.68 (dd, / = 8.3, 3.0 Hz, IH), 6.53 (dd, 7 = 8.3, 4.2 Hz, IH), 5.67 (d, 7H-p = 2.9 Hz, IH), 3.88 (s, 3H), 1.39 (d, 7H-p = 16.6 Hz, 9H); 13C NMR (100 MHz, CDC13) delta 165.6 (d, 7C-p = 15.0 Hz), 161.5 (d, 7C-p = 1.9 Hz), 154.4 (d, 7C_P = 3.4 Hz), 149.2, 136.7, 136.6, 123.0 (d, 7C_P = 1.8 Hz), 122.3 (d, Jc-p = 2.2 Hz), 106.1 (d, 7C_P = 5.1 Hz), 103.6 (d, 7C_P = 5.5 Hz), 103.2 (d, 7C_P = 89.2 Hz), 79.1 (d, Jc-p = 53.9 Hz), 55.6, 34.3 (d, 7C-P = 73.9 Hz), 25.0; 31P NMR (160 MHz, CDC13) delta 61.65; HRMS (ESI) m/z 318.1237 (M + H+), calc. for C17H2iN03P 318.1254.
  • 47
  • [ 24244-60-8 ]
  • [ 1338454-12-8 ]
  • [ 1542795-95-8 ]
  • 48
  • [ 24244-60-8 ]
  • [ 1338453-99-8 ]
  • [ 1542795-98-1 ]
  • 49
  • [ 24244-60-8 ]
  • [ 1477517-24-0 ]
  • [ 1542796-01-9 ]
  • 50
  • [ 694-59-7 ]
  • [ 98-09-9 ]
  • [ 24244-60-8 ]
  • 51
  • [ 694-59-7 ]
  • [ 80-17-1 ]
  • [ 24244-60-8 ]
  • 52
  • [ 24244-60-8 ]
  • [ 1215081-23-4 ]
  • (2R,3S)-3-(tert-butyl)-2-(pyridin-2-yl)-2H-benzo[d][1,3]oxaphosphole 3-oxide [ No CAS ]
  • 53
  • [ 24244-60-8 ]
  • [ 1215081-23-4 ]
  • 2-((2R,3R)-3-(tert-butyl)-2,3-dihydrobenzo[d][1,3]oxaphosphol-2-yl)pyridine [ No CAS ]
  • 54
  • [ 24244-60-8 ]
  • [ 1423122-99-9 ]
  • 55
  • [ 24244-60-8 ]
  • (E)-4-((1-benzylpyridin-2(1H)-ylidene)methyl)-3-bromobenzonitrile [ No CAS ]
  • 56
  • [ 24244-60-8 ]
  • 1-benzyl-2-(4-cyano-2-bromobenzyl)pyridin-1-ium bromide [ No CAS ]
  • 57
  • [ 24244-60-8 ]
  • 2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridine-6-carboxamide [ No CAS ]
  • 2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridine-6-carboxamide [ No CAS ]
  • 58
  • [ 24244-60-8 ]
  • 1-benzyl-6-cyano-9H-indeno[2,1-b]pyridin-1-ium bromide [ No CAS ]
  • 59
  • [ 24244-60-8 ]
  • (4aR,9aS)-1-benzyl-2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridine-6-carbonitrile [ No CAS ]
  • (4aS,9aR)-1-benzyl-2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridine-6-carbonitrile [ No CAS ]
  • 61
  • [ 24244-60-8 ]
  • [ 42872-79-7 ]
  • 3-iodo-4-(pyridin-2-ylmethyl)benzonitrile [ No CAS ]
  • 62
  • [ 24244-60-8 ]
  • [ 42872-74-2 ]
  • 3-bromo-4-(pyridin-2-ylmethyl)benzonitrile [ No CAS ]
  • 63
  • [ 420-04-2 ]
  • [ 89818-46-2 ]
  • [ 24244-60-8 ]
  • N-[oxo(phenyl)(pyridin-2-yl)-λ6-sulfanylidene]cyanamide [ No CAS ]
  • 64
  • [ 3111-54-4 ]
  • [ 24244-60-8 ]
  • N-[oxo(phenyl)(pyridin-2-yl)-λ6-sulfanylidene]cyanamide [ No CAS ]
  • 65
  • [ 108-98-5 ]
  • [ 24244-60-8 ]
  • N-[oxo(phenyl)(pyridin-2-yl)-λ6-sulfanylidene]cyanamide [ No CAS ]
  • 66
  • [ 109-04-6 ]
  • [ 24244-60-8 ]
  • N-[oxo(phenyl)(pyridin-2-yl)-λ6-sulfanylidene]cyanamide [ No CAS ]
  • 67
  • [ 109-04-6 ]
  • [ 98-80-6 ]
  • [ 24244-60-8 ]
  • 68
  • [ 24244-60-8 ]
  • 2-(2-bromobenzenesulfonyl)-pyridine [ No CAS ]
  • 69
  • [ 24244-60-8 ]
  • 2-(2-bromo-6-chlorophenylsulfonyl)pyridine [ No CAS ]
  • 70
  • [ 24244-60-8 ]
  • 2-(2-iodophenylsulfonyl)pyridine [ No CAS ]
  • C11H7I2NO2S [ No CAS ]
  • 71
  • [ 24244-60-8 ]
  • 2-(2-bromobenzenesulfonyl)-pyridine [ No CAS ]
  • C11H7Br2NO2S [ No CAS ]
  • 72
  • [ 24244-60-8 ]
  • 2-(2-chlorophenylsulfonyl)pyridine [ No CAS ]
  • 73
  • [ 24244-60-8 ]
  • 2-(2-chlorophenylsulfonyl)pyridine [ No CAS ]
  • C11H7Cl2NO2S [ No CAS ]
  • 74
  • [ 24244-60-8 ]
  • 2-(2-fluorophenylsulfonyl)pyridine [ No CAS ]
  • 75
  • [ 24244-60-8 ]
  • C11H7Br2NO2S [ No CAS ]
  • 76
  • [ 24244-60-8 ]
  • [ 3375-31-3 ]
  • 2-(2-fluorophenylsulfonyl)pyridine [ No CAS ]
  • C13H11NO4S [ No CAS ]
  • 77
  • [ 24244-60-8 ]
  • [ 64-19-7 ]
  • C13H11NO4S [ No CAS ]
  • 78
  • [ 3111-54-4 ]
  • [ 24244-60-8 ]
  • [ 89818-46-2 ]
  • 79
  • [ 108-98-5 ]
  • [ 24244-60-8 ]
  • 80
  • [ 109-09-1 ]
  • [ 24244-60-8 ]
  • 81
  • [ 109-04-6 ]
  • [ 873-55-2 ]
  • [ 24244-60-8 ]
YieldReaction ConditionsOperation in experiment
71% With iron(III) chloride; tetrabutyl-ammonium chloride; In water; dimethyl sulfoxide; at 140℃; for 20h;Inert atmosphere; General procedure: The sulfinate salt 1 (2 mmol, 1.0 equiv) and halopyridine 2 (1.2 equiv)in DMSO-H2O (3:1, 2 M) were added to a round-bottom flask containing nBu4NCl (0.3 equiv) and FeCl3 (0.01 equiv). The mixture was degassed for 30 min in a sonicator under argon atmosphere, and then heated to 140 C and stirred for 20 h. The resulting mixture was cooled to r.t. and neutralized with 2 M aq NaOH solution, and then extracted with EtOAc (3×). The combined organic phase was washed with distilled H2O, followed by a brine solution, and then was dried over Na2SO4 and filtered. The solvent was then removed under reduced pressure. The residue was purified by column chromatography(silica gel, EtOAc-hexanes-CH2Cl2, 5:45:55) to give the desired sulfonylated pyridine product 3.
  • 82
  • [ 5029-67-4 ]
  • [ 873-55-2 ]
  • [ 24244-60-8 ]
YieldReaction ConditionsOperation in experiment
82% With iron(III) chloride; tetrabutyl-ammonium chloride; In water; dimethyl sulfoxide; at 140℃; for 20h;Inert atmosphere; General procedure: The sulfinate salt 1 (2 mmol, 1.0 equiv) and halopyridine 2 (1.2 equiv)in DMSO-H2O (3:1, 2 M) were added to a round-bottom flask containing nBu4NCl (0.3 equiv) and FeCl3 (0.01 equiv). The mixture was degassed for 30 min in a sonicator under argon atmosphere, and then heated to 140 C and stirred for 20 h. The resulting mixture was cooled to r.t. and neutralized with 2 M aq NaOH solution, and then extracted with EtOAc (3×). The combined organic phase was washed with distilled H2O, followed by a brine solution, and then was dried over Na2SO4 and filtered. The solvent was then removed under reduced pressure. The residue was purified by column chromatography(silica gel, EtOAc-hexanes-CH2Cl2, 5:45:55) to give the desired sulfonylated pyridine product 3.
  • 83
  • [ 24244-60-8 ]
  • [ 996-35-0 ]
  • isopropyl(methyl)[(2-pyridyl)methyl]amine [ No CAS ]
  • 84
  • [ 24244-60-8 ]
  • dichloro(4-methylphenyl)bismuthane [ No CAS ]
  • (4-methylphenyl)bis(2-phenylsulfonylpyridim-3-yl)bismuthane [ No CAS ]
  • 4-aza-10-(4-methylphenyl)phenothiabismine 5,5-dioxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
10%; 68% A mixture of bismuth(III) chloride (211 mg, 0.67 mmol) andtris(4-methylphenyl)bismuthane (162 mg, 0.33 mmol) was stirred in Et2O (8 mL) at room temperature for1 h. To a stirred solution of 2,2,6,6-tetramethylpiperidine (0.37 mL, 2.2 mmol) in THF (10 mL) wasadded dropwise at -78 C butyllithium (2.2 mmol). After 50 min a solution of 10 (219 mg, 1 mmol) inTHF (3 mL) was added at -40 C and the mixture was stirred for 20 min at this temperature. To thissolution was added at -70 C the suspension of dichloro(4-methylphenyl)bismuthane (ca. 1 mmol) thusformed, and the resulting mixture was stirred for 2 h, during which time the temperature was raised toambient. The reaction mixture was poured into brine (50 mL) and extracted with EtOAc (50 mL × 3). Thecombined extracts were concentrated to leave an oily residue, which was purified by chromatography(silica gel) using hexane-EtOAc (3:1) as the eluent to afford 4 and 13 in 68% yield (352 mg, 0.68 mmol)and 10% yield (35 mg, 0.048 mmol), respectively.4-Aza-10-(4-methylphenyl)phenothiabismine 5,5-dioxide (4): colorless solid; mp 232-234 C; 1HNMR (400 MHz, CDCl3): delta 2.35 (3H, s), 7.19 (1H, dd, J = 4.8, 7.4 Hz), 7.26 (2H, d, J = 7.6 Hz), 7.41(1H, dt, J = 1.2, 7.2 Hz), 7.45 (1H, dt, J = 1.2, 7.2 Hz), 7.63 (2H, d, J = 7.6 Hz), 7.87 (1H, dd, J = 1.2, 7.6Hz), 8.21 (1H, dd, J = 1.6, 7.2 Hz), 8.43 (1H, dd, J = 1.2, 7.6 Hz), 8.63 (1H, dd, J = 1.6, 4.4 Hz); 13CNMR (100 MHz, CDCl3): delta 21.6, 127.3, 128.3, 129.0, 132.0, 133.8, 137.5, 138.6, 138.9, 141.9, 146.1,149.0, 151.3 (br), 157.6, 159.2 (br), 163.1 (br). IR (KBr): nu = 1310, 1290, 1160, 1130, 1100, 1080, 1050,1010, 790, 760, 590 and 570 cm-1. Anal. Calcd for C18H14BiNO2S: C, 41.79; H, 2.73; N, 2.71. Found: C,41.97; H, 3.03; N, 2.66.(4-Methylphenyl)bis(2-phenylsulfonylpyridin-3-yl)bismuthane (13): colorless solid; mp 229-231 C;1H NMR (400 MHz, CDCl3): delta 2.36 (3H, s), 7.26 (2H, d, J = 7.6 Hz), 7.28 (2H, dd, J = 4.8, 7.4 Hz), 7.43(4H, t, J = 7.6 Hz), 7.56 (2H, t, J = 7.2 Hz), 7.60 (2H, d, J = 7.6 Hz), 7.86 (4H, d, J = 7.2 Hz), 8.20 (2H,dd, J = 1.6, 7.6 Hz), 8.74 (2H, dd, J = 1.6, 4.4 Hz); 13C NMR (100 MHz, CDCl3): delta 21.6, 128.9, 129.0(×2), 132.3, 133.6, 138.0, 138.1, 139.2, 149.3, 149.7, 157.2 (br), 162.6, 168.5 (br). IR (KBr): nu = 1450,1300, 1160, 1120, 1080, 770, 750, 740, 710, 690, 590 and 570 cm-1. Anal. Calcd for C29H23BiN2O4S2: C,47.29; H, 3.15; N, 3.80. Found: C, 46.90; H, 3.47; N, 3.79.
  • 85
  • [ 5029-67-4 ]
  • diphenyliodonium tetrafluoroborate [ No CAS ]
  • [ 24244-60-8 ]
YieldReaction ConditionsOperation in experiment
65% Add in the reaction tube2-iodopyridine (0.5 mmol, 1.0 equivalent)And sodium dithionite (0.55mmol, 1.1 equivalent),Replace the air in the test tube with high purity nitrogen.Add 3 mL of N,N-dimethylformamide as solvent.The reaction was stirred for 16 hours while heating to 90 C.After the reaction is cooled, it is added to the reaction liquid.Tetrafluoroborate diphenyl iodide(0.75mmol, 1.5 equivalents),Replace the air in the test tube with high purity nitrogen.Stir at 90 C for 10 hours.The reaction was quenched with saturated brine.Extracted with ethyl acetate,Combine the organic phase,dry,Concentrate and separate by column chromatography.The target product IIa (purity: 98%) was obtained in a yield of 65%.
63% (1) Add 0.5 mmol of 2-iodopyridine to the test tube,1.0 mmol of thiourea dioxide,2.0mmol sodium hydroxide,0.05mmol of fluorescein, the air in the test tube was replaced with high-purity nitrogen, and 3mL of dimethyl sulfoxide was added.The reaction was stirred for 16 hours under irradiation of a 25 W fluorescent lamp;(2) After cooling the mixed solution obtained in the step (1), 0.75 mmol of diphenyliodanium tetrafluoroborate is added to the reaction solution.Then replace the air in the test tube with high purity nitrogen.Stir at room temperature for 10 hours;(3) quenching the reaction of the step (2) with saturated brine,The obtained reaction liquid is extracted with ethyl acetate, and the organic phase extracted is sequentially dried, concentrated,Column chromatography separation and solvent removal to obtain a heterocyclic sulfone;The developing solvent for the column chromatography separation was a mixture obtained by mixing ethyl acetate and petroleum ether in a volume ratio of 1:4.The yield of this example was calculated to be 63%.The product was found to have a purity of 98% by HPLC.
Same Skeleton Products
Historical Records

Pharmaceutical Intermediates of
[ 24244-60-8 ]

Perampanel Intermediates

Chemical Structure| 624-28-2

[ 624-28-2 ]

2,5-Dibromopyridine

Chemical Structure| 381248-06-2

[ 381248-06-2 ]

3-Bromo-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one

Chemical Structure| 381233-96-1

[ 381233-96-1 ]

5-Bromo-3-iodopyridin-2-amine

Chemical Structure| 16179-97-8

[ 16179-97-8 ]

2-(Pyridin-2-yl)acetic acid hydrochloride

Chemical Structure| 381233-78-9

[ 381233-78-9 ]

[2,3'-Bipyridin]-6'(1'H)-one

Tradipitant Related Intermediates

Chemical Structure| 1122-54-9

[ 1122-54-9 ]

4-Acetylpyridine

Related Functional Groups of
[ 24244-60-8 ]

Aryls

Chemical Structure| 31596-87-9

[ 31596-87-9 ]

2-(Ethylsulfonyl)aniline

Similarity: 0.60

Chemical Structure| 221615-75-4

[ 221615-75-4 ]

1-(6-Methylpyridin-3-yl)-2-(4-(methylsulfonyl)phenyl)ethanone

Similarity: 0.59

Chemical Structure| 76697-50-2

[ 76697-50-2 ]

1-Amino-2-(isopropylsulphonyl)benzene

Similarity: 0.59

Chemical Structure| 5470-49-5

[ 5470-49-5 ]

4-(Methylsulfonyl)aniline

Similarity: 0.58

Chemical Structure| 35216-39-8

[ 35216-39-8 ]

3-(Methylsulfonyl)aniline

Similarity: 0.58

Sulfones

Chemical Structure| 31596-87-9

[ 31596-87-9 ]

2-(Ethylsulfonyl)aniline

Similarity: 0.60

Chemical Structure| 221615-75-4

[ 221615-75-4 ]

1-(6-Methylpyridin-3-yl)-2-(4-(methylsulfonyl)phenyl)ethanone

Similarity: 0.59

Chemical Structure| 76697-50-2

[ 76697-50-2 ]

1-Amino-2-(isopropylsulphonyl)benzene

Similarity: 0.59

Chemical Structure| 5470-49-5

[ 5470-49-5 ]

4-(Methylsulfonyl)aniline

Similarity: 0.58

Chemical Structure| 35216-39-8

[ 35216-39-8 ]

3-(Methylsulfonyl)aniline

Similarity: 0.58

Related Parent Nucleus of
[ 24244-60-8 ]

Pyridines

Chemical Structure| 21948-75-4

[ 21948-75-4 ]

2-(Methylsulfinyl)pyridine

Similarity: 0.72

Chemical Structure| 221615-75-4

[ 221615-75-4 ]

1-(6-Methylpyridin-3-yl)-2-(4-(methylsulfonyl)phenyl)ethanone

Similarity: 0.59

Chemical Structure| 848141-14-0

[ 848141-14-0 ]

(5-(Methylsulfonyl)pyridin-2-yl)methanamine hydrochloride

Similarity: 0.57

Chemical Structure| 878376-35-3

[ 878376-35-3 ]

Pyridine-2-sulfonyl fluoride

Similarity: 0.57

Chemical Structure| 77555-27-2

[ 77555-27-2 ]

2-(Pyridin-2-ylthio)ethanol

Similarity: 0.57