N-[4-[8-bromo-6-[1-(difluoromethyl)cyclopropyl]-5-methoxy-3-quinolyl]phenyl]methanesulfonamide

Base Information

Chemical Name:N-[4-[8-bromo-6-[1-(difluoromethyl)cyclopropyl]-5-methoxy-3-quinolyl]phenyl]methanesulfonamide
CAS No.:1485749-36-7
Molecular Formula:C₂₁H₁₉BrF₂N₂O₃S
Molecular Weight:497.36
Hs Code.:

Synonyms:N-[4-[8-bromo-6-[1-(difluoromethyl)cyclopropyl]-5-methoxy-3-quinolyl]phenyl]methanesulfonamide

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Chemical Property of N-[4-[8-bromo-6-[1-(difluoromethyl)cyclopropyl]-5-methoxy-3-quinolyl]phenyl]methanesulfonamide

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Technology Process of N-[4-[8-bromo-6-[1-(difluoromethyl)cyclopropyl]-5-methoxy-3-quinolyl]phenyl]methanesulfonamide

There total 8 articles about N-[4-[8-bromo-6-[1-(difluoromethyl)cyclopropyl]-5-methoxy-3-quinolyl]phenyl]methanesulfonamide 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: 91.0%

: 1257833-29-6
3,8-dibromo-6-[1-(difluoromethyl)cyclopropyl]-5-methoxyquinoline

: 380430-57-9
4-(methylsulfonylamino)phenyl boronic acid

: 1485749-36-7
N-[4-[8-bromo-6-[1-(difluoromethyl)cyclopropyl]-5-methoxy-3-quinolyl]phenyl]methanesulfonamide

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In methanol; toluene; at 120 ℃; for 1h; Inert atmosphere; Microwave irradiation;
DOI:10.1021/jm401329s

Reference yield:

: 111049-68-4
methyl 4-amino-5-bromo-2-methoxybenzenecarboxylate

: 1485749-36-7
N-[4-[8-bromo-6-[1-(difluoromethyl)cyclopropyl]-5-methoxy-3-quinolyl]phenyl]methanesulfonamide

Guidance literature:: Multi-step reaction with 8 steps

1.1: bromine; acetic acid / 0.25 h / 100 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / dichloromethane / 0 °C / Inert atmosphere

3.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 19 h / 20 °C / Inert atmosphere

4.1: dichloromethane; water / 0.25 h / Inert atmosphere; Reflux

5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C / Inert atmosphere

6.1: diisobutylaluminium hydride / dichloromethane / 1 h / -78 °C / Inert atmosphere

6.2: Inert atmosphere

7.1: diethylamino-sulfur trifluoride / dichloromethane / 72 h / 20 °C / Inert atmosphere

8.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / methanol; toluene / 1 h / 120 °C / Inert atmosphere; Microwave irradiation

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; carbon tetrabromide; diethylamino-sulfur trifluoride; bromine; sodium hydride; diisobutylaluminium hydride; sodium carbonate; acetic acid; triphenylphosphine; In methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; mineral oil;
DOI:10.1021/jm401329s

Reference yield:

: 1257833-20-7
3,8-dibromo-6-(bromomethyl)-5-methoxyquinoline

: 1485749-36-7
N-[4-[8-bromo-6-[1-(difluoromethyl)cyclopropyl]-5-methoxy-3-quinolyl]phenyl]methanesulfonamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: dichloromethane; water / 0.25 h / Inert atmosphere; Reflux

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / dichloromethane / 1 h / -78 °C / Inert atmosphere

3.2: Inert atmosphere

4.1: diethylamino-sulfur trifluoride / dichloromethane / 72 h / 20 °C / Inert atmosphere

5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / methanol; toluene / 1 h / 120 °C / Inert atmosphere; Microwave irradiation

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; diethylamino-sulfur trifluoride; sodium hydride; diisobutylaluminium hydride; sodium carbonate; In methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; mineral oil;
DOI:10.1021/jm401329s