3-bromo-4-[(1-pyrrolidinyl)methyl]phenyl 6-methoxy-2-[4-[2-(1-pyrrolidinyl)-ethoxy]phenyl]benzo[b]thiophen-3-yl ketone

Base Information

Chemical Name:3-bromo-4-[(1-pyrrolidinyl)methyl]phenyl 6-methoxy-2-[4-[2-(1-pyrrolidinyl)-ethoxy]phenyl]benzo[b]thiophen-3-yl ketone
CAS No.:193966-62-0
Molecular Formula:C₃₃H₃₅BrN₂O₃S
Molecular Weight:619.623
Hs Code.:

Synonyms:3-bromo-4-[(1-pyrrolidinyl)methyl]phenyl 6-methoxy-2-[4-[2-(1-pyrrolidinyl)-ethoxy]phenyl]benzo[b]thiophen-3-yl ketone

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Chemical Property of 3-bromo-4-[(1-pyrrolidinyl)methyl]phenyl 6-methoxy-2-[4-[2-(1-pyrrolidinyl)-ethoxy]phenyl]benzo[b]thiophen-3-yl ketone

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Technology Process of 3-bromo-4-[(1-pyrrolidinyl)methyl]phenyl 6-methoxy-2-[4-[2-(1-pyrrolidinyl)-ethoxy]phenyl]benzo[b]thiophen-3-yl ketone

There total 8 articles about 3-bromo-4-[(1-pyrrolidinyl)methyl]phenyl 6-methoxy-2-[4-[2-(1-pyrrolidinyl)-ethoxy]phenyl]benzo[b]thiophen-3-yl ketone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 55.0%

: 193964-66-8
methyl 3-bromo-4-[(pyrrolidinyl)methyl]benzoate

: 7732-18-5
water

: 193964-15-7
6-methoxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene

: 193966-62-0
3-bromo-4-[(1-pyrrolidinyl)methyl]phenyl 6-methoxy-2-[4-[2-(1-pyrrolidinyl)-ethoxy]phenyl]benzo[b]thiophen-3-yl ketone

Guidance literature:: With thionyl chloride; LiOH; AlCl₃; In tetrahydrofuran; methanol; 1,1-dichloroethane; N,N-dimethyl-formamide; benzene;

Reference yield: 55.0%

: 193964-15-7
6-methoxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene

: 3-bromo-4-[(1-pyrrolidinyl)methyl]benzoyl chloride

: 193966-62-0
3-bromo-4-[(1-pyrrolidinyl)methyl]phenyl 6-methoxy-2-[4-[2-(1-pyrrolidinyl)-ethoxy]phenyl]benzo[b]thiophen-3-yl ketone

Guidance literature:: With aluminium trichloride; In 1,2-dichloro-ethane; at 0 ℃; for 5h;
DOI:10.1021/jm9903388

Reference yield:

: 90560-10-4
6-methoxy-benzo[b]thiophene

: 193966-62-0
3-bromo-4-[(1-pyrrolidinyl)methyl]phenyl 6-methoxy-2-[4-[2-(1-pyrrolidinyl)-ethoxy]phenyl]benzo[b]thiophen-3-yl ketone

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / -60 °C

1.2: hexane; tetrahydrofuran / -60 - 0 °C

2.1: 71 percent / 1.0 N aq. HCl / ethyl acetate

3.1: 55 percent / tetrakis(triphenylphosphine)palladium⁽⁰⁾; 2 N aq. Na₂CO₃ / benzene; ethanol / 3 h / 50 °C

4.1: 55 percent / AlCl₃ / 1,2-dichloro-ethane / 5 h / 0 °C

With hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; aluminium trichloride; sodium carbonate; In tetrahydrofuran; ethanol; hexane; ethyl acetate; 1,2-dichloro-ethane; benzene; 1.1: Metallation / 1.2: Condensation / 2.1: Hydrolysis / 3.1: Suzuki coupling / 4.1: Friedel-Crafts acylation;
DOI:10.1021/jm9903388