methyl 5-(2-methoxyphenyl)pyridine-3-carboxylate

Base Information

• Chemical Name: methyl 5-(2-methoxyphenyl)pyridine-3-carboxylate
• CAS No.: 93349-96-3
• Molecular Formula: C14H13NO3
• Molecular Weight: 243.262
• Hs Code.: 2933399090
• Mol file: 93349-96-3.mol

Synonyms:Methyl 5-(2-methoxyphenyl)nicotinate;

Chemical Property of methyl 5-(2-methoxyphenyl)pyridine-3-carboxylate

Chemical Property:

• Boiling Point: 357.8±32.0 °C(Predicted)
• PKA: 2.77±0.22(Predicted)
• PSA: 48.42000
• Density: 1.159±0.06 g/cm3(Predicted)
• LogP: 2.54380
• Storage Temp.: 2-8°C

Purity/Quality:

95+% ^*data from raw suppliers

Methyl5-(2-methoxyphenyl)nicotinate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of methyl 5-(2-methoxyphenyl)pyridine-3-carboxylate

There total 4 articles about methyl 5-(2-methoxyphenyl)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: 70.0%

5-bromo-3-pyridine carboxylic acid methyl ester (29681-44-5) + 2-Methoxyphenylboronic acid (5720-06-9) → Methyl 5-(2-Methoxyphenyl)nicotinate (93349-96-3)

Guidance literature:

With triethylamine; palladium diacetate; 2*NEt3; In N,N-dimethyl-formamide; at 100 ℃; for 3h;

DOI:10.1021/jo00200a045

Reference yield:

nicotinic acid (59-67-6) → Methyl 5-(2-Methoxyphenyl)nicotinate (93349-96-3)

Guidance literature:

Multi-step reaction with 4 steps

1: SOCl₂ / neat (no solvent) / 24 h / Heating

2: bromine / 1 h / 150 °C

3: CH₂Cl₂ / 1. ice bath 2. 30 min reflux

4: 70 percent / NEt₃ / Pd(OAc)2, 2*NEt₃ / dimethylformamide / 3 h / 100 °C

With thionyl chloride; bromine; triethylamine; palladium diacetate; 2*NEt3; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00200a045

Reference yield:

3-pyridinecarbonyl chloride (10400-19-8) → Methyl 5-(2-Methoxyphenyl)nicotinate (93349-96-3)

Guidance literature:

Multi-step reaction with 3 steps

1: bromine / 1 h / 150 °C

2: CH₂Cl₂ / 1. ice bath 2. 30 min reflux

3: 70 percent / NEt₃ / Pd(OAc)2, 2*NEt₃ / dimethylformamide / 3 h / 100 °C

With bromine; triethylamine; palladium diacetate; 2*NEt3; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00200a045

upstream raw materials:

5-bromo-3-pyridine carboxylic acid methyl ester

2-Methoxyphenylboronic acid

nicotinic acid

3-pyridinecarbonyl chloride

Refernces