84449-86-5

Upstream product

• 84449-71-8 6-methanesulfonyloxy-2-(4-methanesulfonyloxyphenyl)-3-[4-(2-dimethylaminoethoxy)benzoyl]benzo[b]-thiophene, hydrochloride 
• 15570-12-4 3-methoxybenzenethiol 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 63675-74-1 2-(4'-methoxyphenyl)-6-methoxybenzothiophene 
• 84449-65-0 6-<(methylsulfonyl)oxy>-2-<4-<(methylsulfonyl)oxy>phenyl>benzothiophene 
• 63675-73-0 α-(3-methoxyphenyl-thio)-4-methoxyacetophenone 
• 63676-22-2 6-hydroxy-2-(4-hydroxyphenyl)benzo[B]-thiophene 

Relevant academic research and scientific papers

Process for the synthesis of benzothiophenes

The instant invention provides improved processes for preparing benzothiophenes utilizing methanesulfonic acid.

Process for the synthesis of benzothiophenes

The instant invention provides improved processes for preparing benzothiophenes utilizing cation exchange resins.

Process for preparing benzo[b]thiophenes

The preparation of benzo[b]thiophenes by the acylation of alkoxy protected starting materials followed by demethylation using essentially odorless thiol compounds are provided herewith. Demethylation may be carried out in the same reaction vessel without isolation of the acylated, protected material.

Process for the synthesis of benzothiophenes

The instant invention provides improved processes for preparing benzothiophenes utilizing cation exchange resins.

Demethylation process for preparing benzo[b]thiophenes

The preparation of benzo[b]thiophenes by the acylation of alkoxy protected starting materials followed by demethylation using essentially odorless thiol compound (2-methyl-5-t-butyl benzenethiol) are provided herewith. Demethylation may be carried out in the same reaction vessel without isolation of the acylated, protected material.

Process for the synthesis of benzothiophenes

The instant invention provides improved processes for preparing benzothiophenes utilizing methanesulfonic acid.

Process for preparing 3-(4-aminoethoxy-benzoyl) benzo B!-thiophenes

The invention provides a process for preparing 6-alkoxy-3-(4-alkoxyphenyl)benzo B!thiophenes in good yield on a manufacturing scale without generating a thick, potentially yield-reducing, paste. The invention also provides methods for converting a-(-alkoxyphenylthio)-4-alkoxyacetophenones into 6-hydroxy-2-(4-hydroxyphenyl)-3- 4-(2-aminoethoxy)benzoyl!benzo B!thiophenes via acylation of a dialkoxy benzo B!thiophene. Each of these preparations relies on an intramolecular cyclization of a dialkoxy acetophenone derivative to yield a benzo B!thiophene without generating a thick paste that lowers overall yields on a manufacturing scale.

Antiestrogens. 2. Structure-Activity Studies in a Series of 3-Aroyl-2-arylbenzothiophene Derivatives Leading to thien-3-yl>phenyl>methanone Hydrochloride (LY156758), a Remarkably Effective Estrogen Antagonist with On...

In an effort to prepare nonsteroidal antiestrogens demonstrating greater antagonism and less intrinsic estrogenicity than those currently available, a series of 3-aroyl-2-arylbenzothiophene derivatives was synthesized.These compounds were prepared by Friedel-Crafts aroylation of appropriate O-protected 2-arylbenzothiophene nuclei with basic side-chain-bearing benzoyl chlorides followed by removal of the protective groups to provide the desired compounds containing both hydroxyl and basic side-chain functionality.A particularly useful method for the cleavage of aryl methoxy ethers without removal of (dialkylamino)ethoxy side chain functionality elsewhere in the molecule was found to be AlCl3/EtSH.The benzothiophene derivatives were tested for their ability to inhibit the growth-stimulating action of estradiol on the immature rat uterus.Seemingly minor changes in the side-chain amine moiety were found to have profound effects on the ability of the compounds to antagonize estradiol.Analogues having basic side chains containing cyclic (pyrrolidine, piperidine, and hexamethyleneamine) moieties were found to have less intrinsic estrogenicity and to antagonize estradiol action more completely than their noncyclic counterparts.The most effective antiestrogen in the series, compound 44, thien-3-yl>phenyl>methanone, elicited a modest uterotropic activity that did not increase with increasing dose.In antagonism of estradiol, 44 exhibited a degree of inhibition surpassing that of tamoxifen at any dose tested.The new benzothiophene antiestrogen was also shown to have high affinity for rat uterine cycloplasmic estrogen receptor and to be an inhibitor of the growth of DMBA-induced rat mammary tumors.

Synthesis of acylated benzothiophenes

A group of 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-aminoethoxy)benzoyl]benzo[b]thiophenes are prepared by acylation of a methyl-protected starting compound followed by demethylation in a single reaction mixture.

Process for preparing 3-(4-aminoethoxybenzoyl)benzo[b]thiophenes

The use of particularly advantageous protecting groups for the hydroxy groups of 6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophenes provides a high-yielding process for the preparation of such compounds having a 4-(2-aminoethoxy)benzoyl 3-group.