3-{4-[3-(tert-butyldimethylsilanyloxy)propyl]pyridin-3-yl}-3-oxo-2-o-tolylpropionic acid methyl ester

Base Information

• Chemical Name: 3-{4-[3-(tert-butyldimethylsilanyloxy)propyl]pyridin-3-yl}-3-oxo-2-o-tolylpropionic acid methyl ester
• CAS No.: 489466-56-0
• Molecular Formula: C₂₅H₃₅NO₄Si
• Molecular Weight: 441.643
• Mol file: 489466-56-0.mol

Synonyms:3-{4-[3-(tert-butyldimethylsilanyloxy)propyl]pyridin-3-yl}-3-oxo-2-o-tolylpropionic acid methyl ester

Chemical Property of 3-{4-[3-(tert-butyldimethylsilanyloxy)propyl]pyridin-3-yl}-3-oxo-2-o-tolylpropionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-{4-[3-(tert-butyldimethylsilanyloxy)propyl]pyridin-3-yl}-3-oxo-2-o-tolylpropionic acid methyl ester

There total 5 articles about 3-{4-[3-(tert-butyldimethylsilanyloxy)propyl]pyridin-3-yl}-3-oxo-2-o-tolylpropionic acid methyl ester 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:

3-bromo-4-[3-hydroxypropyl]pyridine (229184-01-4) → 3-{4-[3-(tert-butyldimethylsilanyloxy)propyl]pyridin-3-yl}-3-oxo-2-o-tolylpropionic acid methyl ester (489466-56-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / imidazole / CH₂Cl₂ / 17 h / 20 °C

2: 88 percent / N-ethyldiisopropylamine; 1,3-bis(diphenylphosphino)propane / palladium(II) acetate / dimethylformamide / 20 h / 20 - 95 °C

3: 89 percent / potassium trimethylsilanolate / diethyl ether / 48 h / 20 °C

4: dimethylformamide / 1.5 h / 50 °C

5: 1.69 g / 60percent sodium hydride / dimethylformamide / 3.25 h / -10 - 20 °C

With 1H-imidazole; 1,3-bis-(diphenylphosphino)propane; potassium trimethylsilonate; N-ethyl-N,N-diisopropylamine; palladium diacetate; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; 5: Claisen condensation;

DOI:10.1021/jo026411a

Reference yield:

3-Bromo-4-methylpyridin (3430-22-6) → 3-{4-[3-(tert-butyldimethylsilanyloxy)propyl]pyridin-3-yl}-3-oxo-2-o-tolylpropionic acid methyl ester (489466-56-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: diisopropylamine; butyllithium / tetrahydrofuran; hexane / 0.75 h / 5 - 50 °C

1.2: 78 percent / tetrahydrofuran; hexane / 0.5 h / -20 - 0 °C

2.1: 100 percent / imidazole / CH₂Cl₂ / 17 h / 20 °C

3.1: 88 percent / N-ethyldiisopropylamine; 1,3-bis(diphenylphosphino)propane / palladium(II) acetate / dimethylformamide / 20 h / 20 - 95 °C

4.1: 89 percent / potassium trimethylsilanolate / diethyl ether / 48 h / 20 °C

5.1: dimethylformamide / 1.5 h / 50 °C

6.1: 1.69 g / 60percent sodium hydride / dimethylformamide / 3.25 h / -10 - 20 °C

With 1H-imidazole; n-butyllithium; 1,3-bis-(diphenylphosphino)propane; potassium trimethylsilonate; diisopropylamine; N-ethyl-N,N-diisopropylamine; palladium diacetate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; 6.1: Claisen condensation;

DOI:10.1021/jo026411a

Reference yield:

3-bromo-4-[3-(tert-butyldimethylsilanyloxy)propyl]pyridine (380830-44-4) → 3-{4-[3-(tert-butyldimethylsilanyloxy)propyl]pyridin-3-yl}-3-oxo-2-o-tolylpropionic acid methyl ester (489466-56-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / N-ethyldiisopropylamine; 1,3-bis(diphenylphosphino)propane / palladium(II) acetate / dimethylformamide / 20 h / 20 - 95 °C

2: 89 percent / potassium trimethylsilanolate / diethyl ether / 48 h / 20 °C

3: dimethylformamide / 1.5 h / 50 °C

4: 1.69 g / 60percent sodium hydride / dimethylformamide / 3.25 h / -10 - 20 °C

With 1,3-bis-(diphenylphosphino)propane; potassium trimethylsilonate; N-ethyl-N,N-diisopropylamine; palladium diacetate; In diethyl ether; N,N-dimethyl-formamide; 4: Claisen condensation;

DOI:10.1021/jo026411a

upstream raw materials:

3-bromo-4-[3-hydroxypropyl]pyridine

3-Bromo-4-methylpyridin

3-bromo-4-[3-(tert-butyldimethylsilanyloxy)propyl]pyridine

4-[3-(tert-butyldimethylsilanyloxy)propyl]nicotinic acid methyl ester

Downstream raw materials:

4'-(3-hydroxypropyl)-5-(4-methylthiazol-2-yl)-3-o-tolyl-1H-[2,3']bipyridinyl-6-one

1-{4-[3-(tert-butyldimethylsilanyloxy)propyl]pyridin-3-yl}-3-(dimethylamino)-2-o-tolylpropenone

1-{4-[3-(tert-butyldimethylsilanyloxy)propyl]pyridin-3-yl}-2-o-tolylethanone