2-(trimethylsilyl)ethyl 8-cyclopropyl-7-(naphthalen-1-ylmethyl)-5-oxo-2-(phenylethynyl)-5H-thiazolo[3,2-a]pyridine-3-carboxylate

Base Information

Chemical Name:2-(trimethylsilyl)ethyl 8-cyclopropyl-7-(naphthalen-1-ylmethyl)-5-oxo-2-(phenylethynyl)-5H-thiazolo[3,2-a]pyridine-3-carboxylate
CAS No.:1345974-53-9
Molecular Formula:C₃₅H₃₃NO₃SSi
Molecular Weight:575.803
Hs Code.:

Synonyms:2-(trimethylsilyl)ethyl 8-cyclopropyl-7-(naphthalen-1-ylmethyl)-5-oxo-2-(phenylethynyl)-5H-thiazolo[3,2-a]pyridine-3-carboxylate

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Chemical Property of 2-(trimethylsilyl)ethyl 8-cyclopropyl-7-(naphthalen-1-ylmethyl)-5-oxo-2-(phenylethynyl)-5H-thiazolo[3,2-a]pyridine-3-carboxylate

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Technology Process of 2-(trimethylsilyl)ethyl 8-cyclopropyl-7-(naphthalen-1-ylmethyl)-5-oxo-2-(phenylethynyl)-5H-thiazolo[3,2-a]pyridine-3-carboxylate

There total 5 articles about 2-(trimethylsilyl)ethyl 8-cyclopropyl-7-(naphthalen-1-ylmethyl)-5-oxo-2-(phenylethynyl)-5H-thiazolo[3,2-a]pyridine-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: 95.0%

: 1345974-39-1
2-(trimethylsilyl)ethyl 2-bromo-8-cyclopropyl-7-(naphthalen-1-ylmethyl)-5-oxo-5H-thiazolo[3,2-a]pyridine-3-carboxylate

: 536-74-3
phenylacetylene

: 1345974-53-9
2-(trimethylsilyl)ethyl 8-cyclopropyl-7-(naphthalen-1-ylmethyl)-5-oxo-2-(phenylethynyl)-5H-thiazolo[3,2-a]pyridine-3-carboxylate

Guidance literature:: With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 110 ℃; for 0.166667h; Microwave irradiation;
DOI:10.1021/jo201952p

Reference yield:

: 478297-75-5
methyl (3R)-8-cyclopropyl-7-(naphthalen-1-ylmethyl)-5-oxo-2,3-dihydro-5H-[1,3 ]thiazolo[3,2-a]pyridine-3-carboxylate

: 1345974-53-9
2-(trimethylsilyl)ethyl 8-cyclopropyl-7-(naphthalen-1-ylmethyl)-5-oxo-2-(phenylethynyl)-5H-thiazolo[3,2-a]pyridine-3-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: lithium hydroxide / tetrahydrofuran / 0.33 h / 20 °C

2: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.17 h / 20 °C

3: dichloromethane / 0.33 h / 20 °C

4: Bromotrichloromethane; sodium hydride / 2-(Trimethylsilyl)ethanol; acetonitrile / 8 h / 20 °C

5: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 0.17 h / 110 °C / Microwave irradiation

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; oxalyl dichloride; Bromotrichloromethane; sodium hydride; triethylamine; N,N-dimethyl-formamide; lithium hydroxide; In tetrahydrofuran; dichloromethane; 2-(Trimethylsilyl)ethanol; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo201952p

Reference yield:

: C₂₂H₁₈ClNO₂S

: 1345974-53-9
2-(trimethylsilyl)ethyl 8-cyclopropyl-7-(naphthalen-1-ylmethyl)-5-oxo-2-(phenylethynyl)-5H-thiazolo[3,2-a]pyridine-3-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: dichloromethane / 0.33 h / 20 °C

2: Bromotrichloromethane; sodium hydride / 2-(Trimethylsilyl)ethanol; acetonitrile / 8 h / 20 °C

3: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 0.17 h / 110 °C / Microwave irradiation

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; Bromotrichloromethane; sodium hydride; triethylamine; In dichloromethane; 2-(Trimethylsilyl)ethanol; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo201952p