N-[(1S,2S)-2-hydroxycyclohexyl]1-methoxy-4-{[6-(1-methyl-1H-pyrazol-4-yl)pyridine-3-yl]methyl}-2-naphthamide

Base Information

Chemical Name:N-[(1S,2S)-2-hydroxycyclohexyl]1-methoxy-4-{[6-(1-methyl-1H-pyrazol-4-yl)pyridine-3-yl]methyl}-2-naphthamide
CAS No.:1350968-80-7
Molecular Formula:C₂₈H₃₀N₄O₃
Molecular Weight:470.571
Hs Code.:

Synonyms:N-[(1S,2S)-2-hydroxycyclohexyl]1-methoxy-4-{[6-(1-methyl-1H-pyrazol-4-yl)pyridine-3-yl]methyl}-2-naphthamide

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Chemical Property of N-[(1S,2S)-2-hydroxycyclohexyl]1-methoxy-4-{[6-(1-methyl-1H-pyrazol-4-yl)pyridine-3-yl]methyl}-2-naphthamide

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Technology Process of N-[(1S,2S)-2-hydroxycyclohexyl]1-methoxy-4-{[6-(1-methyl-1H-pyrazol-4-yl)pyridine-3-yl]methyl}-2-naphthamide

There total 10 articles about N-[(1S,2S)-2-hydroxycyclohexyl]1-methoxy-4-{[6-(1-methyl-1H-pyrazol-4-yl)pyridine-3-yl]methyl}-2-naphthamide 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:

: 1350968-78-3
4-[(6-chloropyridin-3-yl)methyl]-N-[(1S,2S)-2-hydroxycyclohexyl]-1-methoxy-2-naphthamide

: 761446-44-0
1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

: 1350968-80-7
N-[(1S,2S)-2-hydroxycyclohexyl]1-methoxy-4-{[6-(1-methyl-1H-pyrazol-4-yl)pyridine-3-yl]methyl}-2-naphthamide

Guidance literature:: With caesium carbonate; bis(tri-t-butylphosphine)palladium⁽⁰⁾; In tetrahydrofuran; at 100 ℃; for 16h; Inert atmosphere;

Reference yield:

: 5813-38-7
methyl 1-methoxy-4-bromo-2-naphthoate

: 1350968-80-7
N-[(1S,2S)-2-hydroxycyclohexyl]1-methoxy-4-{[6-(1-methyl-1H-pyrazol-4-yl)pyridine-3-yl]methyl}-2-naphthamide

Guidance literature:: Multi-step reaction with 5 steps

1: bis(tri-t-butylphosphine)palladium⁽⁰⁾ / tetrahydrofuran / 100 °C

2: hydrogen bromide / acetic acid

3: triethylamine / dichloromethane

4: potassium carbonate / N,N-dimethyl-formamide

5: bis(tri-t-butylphosphine)palladium⁽⁰⁾ / tetrahydrofuran / 100 °C

With bis(tri-t-butylphosphine)palladium⁽⁰⁾; hydrogen bromide; potassium carbonate; triethylamine; In tetrahydrofuran; dichloromethane; acetic acid; N,N-dimethyl-formamide; 1: |Negishi Coupling;
DOI:10.1016/j.bmcl.2014.01.012

Reference yield:

: 1350968-92-1
methyl 4-[(6-chloropyridin-3-yl)methyl]-1-methoxy-2-naphthoate

: 1350968-80-7
N-[(1S,2S)-2-hydroxycyclohexyl]1-methoxy-4-{[6-(1-methyl-1H-pyrazol-4-yl)pyridine-3-yl]methyl}-2-naphthamide

Guidance literature:: Multi-step reaction with 4 steps

1: hydrogen bromide / acetic acid

2: triethylamine / dichloromethane

3: potassium carbonate / N,N-dimethyl-formamide

4: bis(tri-t-butylphosphine)palladium⁽⁰⁾ / tetrahydrofuran / 100 °C

With bis(tri-t-butylphosphine)palladium⁽⁰⁾; hydrogen bromide; potassium carbonate; triethylamine; In tetrahydrofuran; dichloromethane; acetic acid; N,N-dimethyl-formamide;
DOI:10.1016/j.bmcl.2014.01.012