63676-19-7

Basic information

• Product Name: Methanone, (4-hydroxyphenyl)[6-methoxy-2-(4-methoxyphenyl)benzo[b]thien-3-yl]-
• CAS NO: 63676-19-7
• Molecular Formula: C23H18O4S
• Molecular Weight: 390.46
• Mol File: 63676-19-7.mol

Chemical Properties

• CAS DataBase Reference: Methanone, (4-hydroxyphenyl)[6-methoxy-2-(4-methoxyphenyl)benzo[b]thien-3-yl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Methanone, (4-hydroxyphenyl)[6-methoxy-2-(4-methoxyphenyl)benzo[b]thien-3-yl]-(63676-19-7)
• EPA Substance Registry System: Methanone, (4-hydroxyphenyl)[6-methoxy-2-(4-methoxyphenyl)benzo[b]thien-3-yl]-(63676-19-7)

Safety Data

• Hazardous Substances Data: 63676-19-7(Hazardous Substances Data)

Upstream product

• 63675-87-6 [6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl](4-methoxy-phenyl)-methanone 
• 811-51-8 sodium thioethylate 
• 75-08-1 ethanethiol 
• 1163701-10-7 (5-methoxy-2-((4-methoxyphenyl)ethynyl)phenyl)(methyl)-sulfane 
• 15570-12-4 3-methoxybenzenethiol 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 63675-73-0 α-(3-methoxyphenyl-thio)-4-methoxyacetophenone 
• 2345-34-8 4-acetyloxy-benzoic acid 
• 27914-73-4 4-acetoxybenzoyl chloride 
• 7099-91-4 p-methoxybenzoylformic acid 
• 200625-51-0 [{4-(1,1-dimethylethyl)dimethylsiloxyphenyl}ethynyl]trimethylsilane 
• 133430-99-6 4-(tert-butyldimethylsilyloxy)iodobenzene 
• 540-38-5 p-Iodophenol 
• 4897-68-1 2-iodo-4-methoxybromobenzene 

Downstream Products

• 342898-48-0 diethyl 2-[5-[4-[(6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl)-carbonyl]-phenoxy]pentyl]-2-(4,4,5,5,5-pentafluoropentyl)malonate 
• 201994-03-8 [2-(4-Methoxyphenyl)-6-methoxybenzo[b]thien-3-yl][4-(8-bromo-octyloxy)phenyl]methanone 
• 222400-98-8 6-Methoxy-2-(4-methoxyphenyl)-3-(4-[1-benzylpiperidin-4-oxy]benzoyl)benzo[b]thiophene 
• 220655-20-9 [6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl][(4-t-butoxyethoxy)phenyl]methanone 
• 222401-06-1 6-Methoxy-2-(4-Methoxyphenyl)-3-(4-[(1-Methylpiperidin-3-yl) methoxy]benzoyl) benzo [b]thiophene 
• 222401-07-2 6-Methoxy-2-(4-methoxyphenyl)-3-(4-[1-methylpiperidin-3-oxy]benzoyl)benzo[b]thiophene 
• 222400-96-6 6-Methoxy-2-(4-methoxyphenyl)-3-(4-[1-methylpiperidin-4-oxy]benzoyl)benzo[b]thiophene 
• 222400-99-9 6-Methoxy-2-(4-methoxyphenyl)-3-(4-[1-hexylpiperidin-4-oxy]benzoyl)benzo[b]thiophene 
• 222401-05-0 6-Methoxy-2-(4-methoxyphenyl)-3-(4-[1-benzylpyrrolidin-3-oxy]benzoyl)benzo[b]thiophene 
• 222401-09-4 6-Methoxy-2-(4-methoxyphenyl)-3-(4-[2-piperidin-1-ylcyclohexoxy]benzoyl)benzo[b]thiophene 
• 222401-10-7 6-Methoxy-2-(4-methoxyphenyl)-3-(4-[2-pyrrolidin-1-ylcyclohexoxy]benzoyl)benzo[b]thiophene 
• 222401-08-3 6-Methoxy-2-(4-Methoxyphenyl)-3-(4-[1-Ethylpiperidin-3-oxy]benzoyl)benzo[b]thiophene 
• 222401-04-9 6-Methoxy-2-(4-methoxyphenyl)-3-(4-[(1-hexylpiperidin-3-yl)methoxy]benzoyl)benzo[b]thiophene 
• 222400-97-7 6-Methoxy-2-(4-methoxyphenyl)-3-(4-[1-ethylpiperidin-4-oxy]benzoyl)benzo[b]thiophene 

Relevant articles and documents

ESTROGEN RECEPTOR TARGETING ANTAGONISTS

The present disclosure relates to compounds that act as antagonists via binding to the ER ligand binding domain non-covalently or covalently, or act as both antagonists and ER protein degraders, and the synthesis of the same. Further, the present disclosure teaches the utilization of such compounds in a treatment for proliferative diseases, including cancer, particularly breast cancer, and especially ER+ breast cancer.

ESTROGEN RECEPTOR PROTEIN DEGRADERS

The present disclosure provides compounds represented by Formula (I): A-L-B and the salts or solvates thereof, wherein A, L, and B are as defined in the specification. Compounds having Formula I are estrogen receptor degraders useful for the treatment of

Method for synthesizing D-Diphenyl formyl-tartaric acid and co-producing methyl benzoate

The invention provides a method for synthesizing D-dibenzoyl tartaric acid and co-producing methyl benzoate. The method comprises the following steps that S1 an organic solvent, D-tartaric acid and lewis acid are added into a reaction bottle, stirred and heated, benzoyl chloride is added dropwise, heat preservation is conducted for 30-90 minutes, a product is cooled to be at 0-5 DEG C, suction filtration is conducted, and a filter cake A and filtrate A are obtained; S2 methyl alcohol is added into the filter cake A and stirred for 30 minutes, suction filtration is conducted, and a filter cakeB and filtrate B are obtained; S3 the filter cake B is added into pure water, heating and back flowing are conducted for 1.5-2.5 hours, a product is cooled to be at 25-30 DEG C, suction filtration isconducted, the filter cake is dried, and D-dibenzoyl tartaric acid is obtained; and S4 an esterification reaction catalyst is added into the filtrate B, back flowing is conducted, alkali is added to adjust the pH value, atmospheric distillation is conducted, water is added to wash the product, vacuum rectification is conducted, and the methyl benzoate is obtained. The method has the advantages that the technology is simple, the operation is convenient, the condition is moderate, the product chromaticity is good, the method is environmentally friendly, the cost is low, the product yield is high, and the product purity is high.

A pizotifen derivative and its preparation method (by machine translation)

The invention discloses a pizotifen derivatives, its molecular formula is The preparation of the pizotifen derivatives raw materials used is simple, its reaction condition is easy to reach, and has a higher yield, in the reaction process also will not produce harmful substances, is a raw material and the reaction conditions are simple pizotifen derivatives. (by machine translation)

Discovery of ERD-308 as a Highly Potent Proteolysis Targeting Chimera (PROTAC) Degrader of Estrogen Receptor (ER)

The estrogen receptor (ER) is a validated target for the treatment of estrogen receptor-positive (ER+) breast cancer. Here, we describe the design, synthesis, and extensive structure-activity relationship (SAR) studies of small-molecule ERα degraders base

Direct synthesis of 3-acylbenzothiophenes: Via the radical cyclization of 2-alkynylthioanisoles with α-oxocarboxylic acids

A radical cascade cyclization of 2-alkynylthioanisoles with α-oxocarboxylic acids with AgNO3 has been described. This reaction provides a novel route to directly access 3-acylbenzothiophenes from simple chemical feedstocks. In particular, the utility of the approach was demonstrated by its application to the synthesis of a polymerization inhibitor and a raloxifene precursor.

Efficient synthesis of 3-benzoyl Benzo[b]thiophenes and raloxifene via Mercury(II)-Catalyzed cyclization of 2-alkynylphenyl alkyl sulfoxides

The unique selective estrogen receptor modulator, Raloxifene (1), and antitubulin agent 2 were synthesized through the key intermediate, 4-methoxybenzyl 2-bromo-4-methoxyphenyl sulfoxide (6), respectively. It was found that compared with the o-sulfanyl aryl bromides, the sulfinyl group at ortho position accelerated the Sonogashira coupling reaction of aryl bromides. Thus, compound 6 was coupled with 3,4,5-trimethoxyphenyl acetylene, followed by mercury-catalyzed cyclization reaction afford compound 2 in 79% overall yield. Raloxifene (1) was prepared from compound 6 in four steps and 33% overall yield via coupling reaction with 1-trimethylsily-2-(4-tert-butyldimethylsiloxy)phenylethyne, mercury-catalyzed cyclization reaction, alkylation and demethylation.

Sulfoxide compound and method of producing benzothiophene derivatives using the same

A sulfoxide compound and method of producing benzothiophene derivatives using the same are provided. The sulfoxide compound is represented by formula (I), wherein R1 and R2 are individually and independently benzoyl group; alkyl, acyl or silyl group of C1-C6 straight chain or branched chain; or alkenyl group of C3-C6 straight chain or branched chain; and X is halogen atom. The sulfoxide compound reacts with alkynyl compound, and then the synthesis efficiency of benzothiophene derivatives can be effectively increased.

Diversity-Oriented Synthesis of Substituted Benzo[b]thiophenes and Their Hetero-Fused Analogues through Palladium-Catalyzed Oxidative C-H Functionalization/Intramolecular Arylthiolation

An efficient, high yielding route to multisubstituted benzo[b]thiophenes has been developed through palladium-catalyzed intramolecular oxidative C-H functionalization-arylthiolation of enethiolate salts of α-aryl-β-(het)aryl/alkyl-β-mercaptoacrylonitriles/acrylates or acrylophenones. The overall strategy involves a one-pot, two-step process in which enethiolate salts [generated in situ through base-mediated condensation of substituted arylacetonitriles, deoxybenzoins, or arylacetates with (het)aryl (or alkyl) dithioates] are subjected to intramolecular C-H functionalization-arylthiolation under the influence of a palladium acetate (or palladium chloride)/cupric acetate catalytic system and tetrabutylammonium bromide as additive in N,N-dimethylformamide (DMF) as solvent. In a few cases, the yields of benzo[b]thiophenes were better in a two-step process by employing the corresponding enethiols as substrates. In a few examples, Pd(OAc)2 (or PdCl2) catalyst in the presence of oxygen was found to be more efficient than cupric acetate as reoxidant, furnishing benzothiophenes in improved yields by avoiding formation of side products. The method is compatible with a diverse range of substituents on the aryl ring as well as on the 2- and 3-positions of the benzothiophene scaffold. The protocol could also be extended to the synthesis of a raloxifene precursor and a tubulin polymerization inhibitor in good yields. The versatility of this newly developed method was further demonstrated by elaborating it for the synthesis of substituted thieno-fused heterocycles such as thieno[2,3-b]thiophenes, thieno[2,3-b]indoles, thieno[3,2-c]pyrazole, and thieno[2,3-b]pyridines in high yields. A probable mechanism involving intramolecular electrophilic arylthiolation via either a Pd-S adduct or palladacycle intermediate has been proposed on the basis of experimental studies.

A process for preparing benzo[b]thiophene derivatives

The present invention relates in general to the field of organic chemistry, and in particular to the preparation of benzo[b]thiophene derivatives. These benzo[b]thiophene derivatives are useful as intermediates in the synthesis of pharmaceutically active agents such as raloxifene or derivatives thereof.