Simple exploration of 3-(Bromomethyl)benzo[b]thiophene

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Disclosed are chemical entities which are compounds of formula (I) : or a pharmaceutically acceptable salt thereof, wherein R1, R2, and Ra have the values described herein. Chemical entities according to the disclosure can be useful as inhibitors of ATG7. Further provided are pharmaceutical compositions comprising a chemical entity of the disclosure and methods of using the compositions in the treatment of cancer.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Benzimidazole derivatives

A benzimidazole derivative or its medically acceptable salt, represented by the following formula (1), that is a human chymase activity inhibitor capable of being applied clinically: 1wherein, R1 and R2 represent a hydrogen atom, an alkyl group or an alkoxy group, etc., A represents an alkylene group or an alkenylene group, E represents ?COOR3, ?SO3R3, ?CONHR3 or ?SO2NHR3, etc., G represents an alkylene group, M represents a single bond or ?S(O)m. J represents a heterocyclic group, and X represents ?CH= or a nitrogen atom.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Pd(OH)2/C, a Practical and Efficient Catalyst for the Carboxylation of Benzylic Bromides with Carbon Monoxide

A simple, efficient, cheap, and broadly applicable system for the carboxylation of benzylic bromides with carbon monoxide and water is reported. Upon simple reaction with only 2.5 wt % of Pearlman’s catalyst and 10 mol % of tetrabutylammonium bromide in tetrahydrofuran at 110 C for 4 h, a range of benzylic bromides can be smoothly converted to the corresponding arylacetic acids in good to excellent yields after simple extraction and acid-base wash. The reaction was found to be broadly applicable, scalable, and could be successfully extended to the use of ex situ-generated carbon monoxide and applied to the synthesis of the nonsteroidal anti-inflammatory drug diclofenac.

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Benzothiophene – Wikipedia,
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Some scientific research about 3-(Bromomethyl)benzo[b]thiophene

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Synthesis and Structure-Activity Relationship of Benzothienylallylamine Antimycotics

Benzothiophene analogues of the allylamine antimycotic terbinafine (2) bearing the side chain at various positions and optionally substituted by halogen have been prepared and their antifungal activity studied.Derivatives bearing the side chain at positions 3, 4, or 7 are bioequivalents of 2.Compounds containing the allylamine side chain at position 7, with a further substituent at position 3, showed significantly enhanced activity against Candida albicans, an effect which appears to be specifically linked only to this particular substitution pattern. 3-Chloro-7-benzothienyl derivative 7m was found to be the most potent allylamine antimycotic identified so far.In general, substituted benzothiophenes can be used not only as potential equivalents of naphthalene in bioactive compoudns but also as a tool to selectively modify biological activities.

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Phase-transfer-catalyzed asymmetric synthesis of 1,1-disubstituted tetrahydroisoquinolines

A highly efficient catalytic asymmetric synthesis of 1,1-disubstituted tetrahydroisoquinolines has been achieved via asymmetric alkylation or Michael addition of 1-cyanotetrahydroisoquinolines using binaphthyl-modified N-spiro-type chiral phase-transfer catalysts. Copyright

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Benzothiophene – Wikipedia,
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Treatment of 2-isocyano-N-<(S)-1'-phenylethyl>propionamide (3a) with butyllithium or potassium tert-butoxide (-70 deg C, tetrahydrofuran) initially causes metalation and subsequent (at ca. -20 deg C) cyclization to give the anionized 4-methyl-1-<(S)-1'-phenylethyl>-2-imidazolin-5-one (8).This reacts with benzyl or heterobenzyl halides to yield (4S)-4-benzyl- or (4S)-4-heterobenzyl-4-methyl-1-<(S)-1'-phenylethyl>-2-imidazolin-5-ones 9 with an asymmetric induction (d.e. = diastereomeric excess) >>95percent.Hydrolysis of 9 gives alpha-methylphenylalanine or its analogues of type 11 (nearly optically pure) which have been characterized as their N-acetyl derivatives 12.More over, (S)-1-phenylethylamine (2a), the chiral auxiliary compound, is recovered. – With non-benzylic alkyl halides d.e. is much lower (i.e. with allyl bromide 17percent, with cyclohexylmethyl iodide 35percent). – A model concept for the asymmetric induction which also explains the extremely high asymmetric induction with benzyl halides is proposed. – Methods for the synthesis of 2- unsubstituted 4-alkyl-2-imidazolin-5-ones (type 9a, 15-17) and 2-substituted 4-alkyl-2-imidazolin-5-ones (type 18-20) are described. – The X-ray analysis of 4-benzyl-4-methyl-1-(1′-phenylethyl)-2-imidazolin-5-one (9b) shows a) the “phenyl inside conformation” (folded conformation) for the C-4-benzyl group and b) C-1′ fixed in such a way that the hydrogen atom of the phenylethyl group lies in the heterocyclic plane, pointing towards the carbonyl oxygen.

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Benzothiophene – Wikipedia,
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The important role of C9H7BrS

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Pyrrolo[1,4]diazepines, via thermolyse of carbonylazides, and [3,2,2]cyclazines, via Diels-Alder reaction of [f]indolizines, annelated to [1]benzothiophene

Easy access to fused tricyclic pyrrolo[1,2-a][1]benzothieno[2,3-e][1,4]diazepines from the corresponding carbonyl azides by thermolysis in acetic acid is described. Moreover, new [1]benzothieno[2,3(3,2)-f]indolizines were synthesized in one-pot from 2(3)-(2-formylpyrrol-1-ylmethyl)-[1]benzothiophene and with diethyl acetylenedicarboxylate (DEAD) they led regiospecifically to [3,2,2] cyclazines fused to a [1]benzothiophene ring by 1,3-dipolar cycloaddition reaction rather than Diels-Alder adducts.

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Benzothiophene – Wikipedia,
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[1]Benzothienoindolizidinones and [1]Benzothienoquinolizidinones: Synthesis and Schmidt rearrangement into [1,3]diazepines derivatives

[1]Benzothienoindolizidinones 5ac,ae,bc and [1]Benzothienoquinolizidinone 5ad were synthesized from 2(3)-bromethyl[1]benzothiophene and methyl prolinate, methyl oxoprolinate and ethyl pipecolinate. The Schmidt rearrangement of ketones 5 led exclusively to the [1,3]diazepines derivatives 6.

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Extended knowledge of C9H7BrS

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One-pot transformation of methylarenes into aromatic aldehydes under metal-free conditions

On the basis of studies of the transformation of benzylic bromides into the corresponding aromatic aldehydes by treatment with N-methylmorpholine N-oxide, various methylarenes were treated either with DBDMH in the presence of AIBN in acetonitrile at reflux (Method A) or with NBS in CCl4 under irradiation with a tungsten lamp at 30 C (Method B), followed by treatment with N-methylmorpholine N-oxide to provide aromatic aldehydes in good yields. These methods could be adopted in one-pot transformations of methylarenes into aromatic aldehydes under conditions free of less toxic reagents and transition metals. Copyright

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Archives for Chemistry Experiments of 1196-19-6

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Synthetic Utility of Arylmethylsulfones: Annulative pi-Extension of Aromatics and Hetero-aromatics Involving Pd(0)-Catalyzed Heck Coupling Reactions

A straightforward and general method for the synthesis of annulated thiophene, dibenzothiophene, and carbazoles analogues has been achieved involving alkylation of 2-bromo-1-(phenylsulfonylmethyl)arene/heteroarene with arylmethyl bromides/heteroarylmethyl bromides using t-BuOK as a base in DMF, followed by Pd(0)-mediated intramolecular Heck coupling in the presence of K2CO3 in DMF at 80-140 C. The attractive feature of this protocol is that a wide variety of pi-conjugated heterocycles could be readily accessed by an appropriate choice of arylmethylsulfones and benzylic bromides.

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