5'-(3-Cyano-5-fluorophenyl)-spiro[cyclopentane-1,3'-[3H]indol]-2'(1'H)-one

Base Information

Chemical Name:5'-(3-Cyano-5-fluorophenyl)-spiro[cyclopentane-1,3'-[3H]indol]-2'(1'H)-one
CAS No.:304875-56-7
Molecular Formula:C₁₉H₁₅FN₂O
Molecular Weight:306.339
Hs Code.:

Synonyms:5'-(3-Cyano-5-fluorophenyl)-spiro[cyclopentane-1,3'-[3H]indol]-2'(1'H)-one

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Chemical Property of 5'-(3-Cyano-5-fluorophenyl)-spiro[cyclopentane-1,3'-[3H]indol]-2'(1'H)-one

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Technology Process of 5'-(3-Cyano-5-fluorophenyl)-spiro[cyclopentane-1,3'-[3H]indol]-2'(1'H)-one

There total 5 articles about 5'-(3-Cyano-5-fluorophenyl)-spiro[cyclopentane-1,3'-[3H]indol]-2'(1'H)-one 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: 44.0%

: 179898-34-1
3-bromo-5-fluorobenzonitrile

: 304876-35-5
2'-oxo-1-spiro[cyclopentane-1,3'-indol]-5'-ylboronic acid

: 304875-56-7
5'-(3-Cyano-5-fluorophenyl)-spiro[cyclopentane-1,3'-[3H]indol]-2'(1'H)-one

Guidance literature:: 3-bromo-5-fluorobenzonitrile; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,2-dimethoxyethane; for 0.333333h; Nitrogen atmosphere;

2'-oxo-1-spiro[cyclopentane-1,3'-indol]-5'-ylboronic acid; With sodium carbonate; In 1,2-dimethoxyethane; for 18h;

Reference yield: 44.0%

: (spiro[cyclopentane-1,3'-[3H]indol]-2'(1'H)-one-5-yl) boronic acid

: 179898-34-1
3-bromo-5-fluorobenzonitrile

: 304875-56-7
5'-(3-Cyano-5-fluorophenyl)-spiro[cyclopentane-1,3'-[3H]indol]-2'(1'H)-one

Guidance literature:: With sodium carbonate; tetrakis(triphenylphosphine)palladium ⁽⁰⁾; In 1,2-dimethoxyethane; water;

Reference yield:

: 59-48-3
2-oxoindole

: 304875-56-7
5'-(3-Cyano-5-fluorophenyl)-spiro[cyclopentane-1,3'-[3H]indol]-2'(1'H)-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-BuLi; TMEDA / tetrahydrofuran / -78 °C

1.2: tetrahydrofuran

2.1: Br₂; NaOAc; AcOH / 20 °C

3.1: NaH / tetrahydrofuran

3.2: n-BuLi; (iPrO)3B / tetrahydrofuran

4.1: Pd(PPh₃)4; Na₂CO₃ / 1,2-dimethoxy-ethane; H₂O / 90 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; bromine; sodium acetate; sodium hydride; sodium carbonate; acetic acid; In tetrahydrofuran; 1,2-dimethoxyethane; water; 4.1: Suzuki coupling;
DOI:10.1016/S0960-894X(02)00746-1