Analyzing the synthesis route of 20532-33-6

20532-33-6, 20532-33-6 5-Chlorobenzothiophene 11309754, abenzothiophene compound, is more and more widely used in various.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.20532-33-6,5-Chlorobenzothiophene,as a common compound, the synthetic route is as follows.

[000270] To a solution of 5-chlorobenzo[6]thiophene (2.00 g, 11.83 mmol) in THF (50 mL) was added dropwise n-BuLi in THF (5.20 mL, 13.01 mmol) at -78 C. Then it was stirred at -50 C for 1 h. Diethyl oxalate (4.32 g, 29.58 mmol) was added to the mixture quickly at -78 C. The mixture was stirred at -50 C for 1 h. It was quenched with acetic acid, diluted with ethyl acetate (200 mL), washed with water and brine, dried with anhydrous Na2S04, and evaporated to give a residue which was washed with petroleum ether to obtain Compound 3A (2.60 g, yield 82%) as a light yellow solid. LCMS: 269 [M+l] +; 1H-NMR (CDC13, 400 MHz) major characteristic peaks: delta (ppm) 1.46 (t, J= 7.6 Hz, 3H), 4.45-4.51 (m, 2H), 7.48 (d, J= 8.8 Hz, 1H), 7.82 (d, J= 8.8 Hz, 1H), 7.92 (s, 1H), 8.37 (s, 1H).

20532-33-6, 20532-33-6 5-Chlorobenzothiophene 11309754, abenzothiophene compound, is more and more widely used in various.

Reference£º
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHU, Daniel; BRIDGES, Alexander, James; WO2015/42397; (2015); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

Brief introduction of 20532-33-6

20532-33-6 5-Chlorobenzothiophene 11309754, abenzothiophene compound, is more and more widely used in various.

20532-33-6, 5-Chlorobenzothiophene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of Br2 (160 mg, 1.00 mmol) in methylene chloride (5 mL) was added dropwise to a 25 mL round bottom flask charged with 5-chlorobenzo[b]thiophene (169 mg, 1.00 mmol), and NaOAc (164 mg, 2.00 mmol) in methylene chloride (10 mL) at 0 C. over 5 min. The resulting mixture was added dropwise into boiling polyphosphoric acid (1 g) in chlorobenzene (5 mL) over 5 min. Work-up: the mixture was poured into 10% aqueous solution of NaHSO3 (20 mL), extracted three times with EtOAc (20 mL), and dried over MgSO4. The mixture was concentrated to give the title compound in 0.247 g (99% yield) as a pale yellow solid (mp 84 C.). 1H-NMR (300 MHz, DMSO-d6): delta:: 7.45-7.56 (m, 1H), 7.76-7.77 (d, 1H), 7.99-8.18 (m, 2H), 20532-33-6

20532-33-6 5-Chlorobenzothiophene 11309754, abenzothiophene compound, is more and more widely used in various.

Reference£º
Patent; Kahraman, Mehmet; Borchardt, Allen J.; Cook, Travis G.; Davis, Robert L.; Gardiner, Elizabeth M.M.; Malecha, James W.; Noble, Stewart A.; Prins, Thomas J.; US2008/21026; (2008); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

New learning discoveries about 20532-33-6

The synthetic route of 20532-33-6 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.20532-33-6,5-Chlorobenzothiophene,as a common compound, the synthetic route is as follows.

Unless otherwise specified, under an inert atmosphere C1 (31.9mg, 0.04 mmol, 10 mol %), aryl halide (0.4 mmol), boronic acid(1.2 mmol), and KOtBu (157.1 mg, 1.4 mmol), were added to anoven-dried 4 dram vial containing a magnetic stir bar. 1,4-Dioxane (4 mL) and EtOH (101.7 muL) were added. The vial wassealed with a screwcap featuring a PTFE/silicone septum andwas removed from the glovebox. The reaction mixture wasmagnetically stirred for 16 h in a temperature-controlled aluminumheating block set to 60 C. After 16 h, the reactionmixture was cooled to room temperature, taken up in EtOAc (ca.10 mL), and extracted with distilled water (3 ¡Á 10 mL). Theorganic layer was dried over anhydrous Na2SO4, filtered, andconcentrated with the aid of a rotary evaporator., 20532-33-6

The synthetic route of 20532-33-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Sawatzky, Ryan S.; Stradiotto, Mark; Synlett; vol. 29; 6; (2018); p. 799 – 804;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

Brief introduction of 20532-33-6

20532-33-6 5-Chlorobenzothiophene 11309754, abenzothiophene compound, is more and more widely used in various.

20532-33-6, 5-Chlorobenzothiophene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Reference Example 32 Preparation of 5-chlorobenzo[b]thiophene-2-carboxaldehyde To a solution of 5-chlorobenzo[b]thiophene (6.14 g) in THF (120 ml) was added n-BuLi (1.6 M solution in hexane, 27.3 ml) at -78 C., and the mixture was stirred for 2 hours. To this mixture was added DMF (8.5 ml), and the mixture was stirred for 1 hour at -78 C. to -30 C. The reaction was quenched by the addition of water and allowed to warm to room temperature. The organic layer was separated, diluted with ethyl acetate, washed with 10% citric acid solution, brine, dried over MgSO4, and concentrated. The residue was titurated with diisopropylether to give the titled compound as colorless crystals (5.92 g). 1H-NMR (CDCl3) delta: 7.48 (1dd, J=8.8, 2.0 Hz), 7.84 (1H, d, J=8.8 Hz), 7.94 (1H, d, J=2.0 Hz), 7.97 (1H, s), 10.12 (1H, s). IR (KBr): 1678, 1516, 1140 cm-1.

20532-33-6 5-Chlorobenzothiophene 11309754, abenzothiophene compound, is more and more widely used in various.

Reference£º
Patent; Takeda Chemical Industries, Ltd.; US6420375; (2002); B1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

Brief introduction of 20532-33-6

20532-33-6 5-Chlorobenzothiophene 11309754, abenzothiophene compound, is more and more widely used in various.

20532-33-6, 5-Chlorobenzothiophene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

a) Aluminium chloride (2.0g) was added in portions to a solution of 5-chlorobenzo[b]thiophene (1.7g) in benzene (50ml). After stirring for a further 1/2 hour, the reaction mixture was poured onto ice/dilute hydrochloric acid mixture and the organic layer separated. The aqueous was further extracted with diethyl ether. The combined extracts were dried and the solvent removed. The residue was stirred with hexane and the insoluble 5-chlorobenzo[b]thiophene dimer removed. Evaporation of the hexane gave a 50:50 mixture (as established by N.m.r.) of 5-chloro-2,3-dihydro-3-phenylbenzo[b]thiophene and 5-chloro-2,3-dihydro-2-phenylbenzo[b]thiophene as a colourless oil (1.3g).

20532-33-6 5-Chlorobenzothiophene 11309754, abenzothiophene compound, is more and more widely used in various.

Reference£º
Patent; SHELL INTERNATIONALE RESEARCH, MAATSCHAPPIJ B.V.; EP526951; (1993); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

Some tips on 20532-33-6

As the paragraph descriping shows that 20532-33-6 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.20532-33-6,5-Chlorobenzothiophene,as a common compound, the synthetic route is as follows.

EXAMPLE 67 5-chloro-2-(4-hydroxy-1-methylpiperidin-4-yl)benzothiophene A solution of 0.300 gm (1.78 mMol) 5-chlorobenzothiophene in 20 mL tetrahydrofuran was cooled to -78 C. To the cooled solution was then added 1.27 mL (1.78 mMol) n-butyllithium (1.2M in tetrahydrofuran) and the reaction mixture stirred for 1 hour after the addition was complete. To this solution was added 0.218 mL (1.78 mMol) 1-methyl-4-piperidone and the reaction mixture was allowed to warm to 0 C. The reaction mixture was quenched with saturated aqueous sodium bicarbonate and partitioned by the addition of hexane/diethyl ether. The organic phase was washed with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated under reduced pressure to provide 0.34 gm of a tan solid. This residue was subjected to silica gel chromatography, eluding with chloroform containing 5% methanol. Fractions containing product were combined and concentrated under reduced pressure to provide 0.34 gm (68%) of the title compound as an off-white solid. MS(FD): m/e=281 (M+)

As the paragraph descriping shows that 20532-33-6 is playing an increasingly important role.

Reference£º
Patent; Eli Lilly and Company; US5846982; (1998); A;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

New learning discoveries about 20532-33-6

The synthetic route of 20532-33-6 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.20532-33-6,5-Chlorobenzothiophene,as a common compound, the synthetic route is as follows.

Preparation 22 Preparation of 3-bromo-5-chlorobenzo[b]thiophene A solution of bromine (0.31 g, 1.95 mmol) in 1.0 ml glacial acetic acid was added to a stirred solution of 5-chlorobenzo[b]thiophene (0.300 g, 1.77 mmol) in glacial acetic acid (1.0 ml) under nitrogen atmosphere. The reaction was heated to 50 C. for 4 hours, the volatiles removed under reduced pressure, the residue diluted in methylene chloride, washed with aq. sodium bicarbonate and with brine and dried over sodium sulfate. Evaporation gave 0.335 g (76%) of a tan solid. mp 85-86 C., FDMS m/e=249 (M+2).

The synthetic route of 20532-33-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Eli Lilly and Company; US5627196; (1997); A;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem