methyl 6-chloro-5-[4-(1-hydroxycyclobutyl)phenyl]-1H-indole-3-carboxylate

Base Information

Chemical Name:methyl 6-chloro-5-[4-(1-hydroxycyclobutyl)phenyl]-1H-indole-3-carboxylate
CAS No.:1467059-92-2
Molecular Formula:C₂₀H₁₈ClNO₃
Molecular Weight:355.821
Hs Code.:

Synonyms:methyl 6-chloro-5-[4-(1-hydroxycyclobutyl)phenyl]-1H-indole-3-carboxylate

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Chemical Property of methyl 6-chloro-5-[4-(1-hydroxycyclobutyl)phenyl]-1H-indole-3-carboxylate

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Technology Process of methyl 6-chloro-5-[4-(1-hydroxycyclobutyl)phenyl]-1H-indole-3-carboxylate

There total 8 articles about methyl 6-chloro-5-[4-(1-hydroxycyclobutyl)phenyl]-1H-indole-3-carboxylate 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: 77.0%

: 1467059-91-1
methyl 5-bromo-6-chloro-1H-indole-3-carboxylate

: 1467062-11-8
[4-(1-hydroxycyclobutyl)phenyl]boronic acid

: 1467059-92-2
methyl 6-chloro-5-[4-(1-hydroxycyclobutyl)phenyl]-1H-indole-3-carboxylate

Guidance literature:: With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In 2-methyltetrahydrofuran; water; at 74 ℃; for 2h; Inert atmosphere; Large scale;
DOI:10.1021/acs.oprd.8b00059

Reference yield:

: 19936-14-2
1-(4-bromophenyl)cyclobutan-1-ol

: 1467059-92-2
methyl 6-chloro-5-[4-(1-hydroxycyclobutyl)phenyl]-1H-indole-3-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); XPhos; sodium t-butanolate; tetrahydroxydiboron; potassium acetate / ethanol / 3 h / 80 °C / Inert atmosphere

2: water; bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / 2-methyltetrahydrofuran / 18.5 h / 20 - 75 °C / Inert atmosphere; Sealed tube

With bis-triphenylphosphine-palladium(II) chloride; tetrahydroxydiboron; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); water; potassium acetate; potassium carbonate; sodium t-butanolate; XPhos; In 2-methyltetrahydrofuran; ethanol; 2: |Suzuki Coupling;
DOI:10.1021/acs.jmedchem.6b00866

Reference yield:

: 122531-09-3
5-bromo-6-chloro-1H-indole

: 1467059-92-2
methyl 6-chloro-5-[4-(1-hydroxycyclobutyl)phenyl]-1H-indole-3-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: dmap; pyridine / tetrahydrofuran / 64 h / 0 - 20 °C

1.2: 0.17 h / 10 °C

1.3: 2 h

2.1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / water; 2-methyltetrahydrofuran / 18.5 h / 75 °C / Inert atmosphere

With pyridine; dmap; bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In tetrahydrofuran; 2-methyltetrahydrofuran; water;