Furo[3,4-c]pyridine-1-carboxylic acid, 4,6-dichloro-3-(diethylamino)-, methyl ester

Base Information

• Chemical Name: Furo[3,4-c]pyridine-1-carboxylic acid, 4,6-dichloro-3-(diethylamino)-, methyl ester
• CAS No.: 220559-34-2
• Molecular Formula: C13H14 Cl2 N2 O3
• Molecular Weight: 0
• Mol file: 220559-34-2.mol

Synonyms:Furo[3,4-c]pyridine-1-carboxylic acid, 4,6-dichloro-3-(diethylamino)-, methyl ester

Chemical Property of Furo[3,4-c]pyridine-1-carboxylic acid, 4,6-dichloro-3-(diethylamino)-, methyl ester

Chemical Property:

• PSA: 55.57000
• LogP: 3.76740

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Furo[3,4-c]pyridine-1-carboxylic acid, 4,6-dichloro-3-(diethylamino)-, methyl ester

There total 8 articles about Furo[3,4-c]pyridine-1-carboxylic acid, 4,6-dichloro-3-(diethylamino)-, 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: 50.0%

diazo-(2,6-dichloro-3-diethylcarbamoyl-pyridin-4-yl)-acetic acid methyl ester (220559-33-1) → methyl 4.6-dichloro-3-(diethylamino)furo[3,4-c]pyridine-1-carboxylate (220559-34-2)

Guidance literature:

With dirhodium tetraacetate; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1016/S0040-4039(98)02414-9

Reference yield:

2,6-dichloro-4-methylnicotinonitrile (875-35-4) → methyl 4.6-dichloro-3-(diethylamino)furo[3,4-c]pyridine-1-carboxylate (220559-34-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 66 percent / DIBALH / CH₂Cl₂; toluene / 2 h / -78 - 20 °C

2: 78 percent / NaClO₂; NaH₂PO₄*2H₂O / 2-methyl-propan-2-ol; H₂O / 4 h / 10 - 25 °C

3: (COCl)2 / benzene / 3 h / Heating

4: pyridine / CH₂Cl₂ / 2 h / 20 °C

5: 53 percent / LDA; HMPA / tetrahydrofuran / 4 h / -78 - 20 °C

6: 85 percent / p-acetamidobenzenesulfonyl azide; Et₃N / acetonitrile / 12 h / 0 - 20 °C

7: 50 percent / Rh₂(OAc)4 / CH₂Cl₂ / 1 h / 20 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium chlorite; sodium dihydrogenphosphate; oxalyl dichloride; 4-acetamidobenzenesulfonyl azide; diisobutylaluminium hydride; triethylamine; lithium diisopropyl amide; dirhodium tetraacetate; In tetrahydrofuran; dichloromethane; water; toluene; acetonitrile; tert-butyl alcohol; benzene; 1: Reduction / 2: Oxidation / 3: Substitution / 4: Substitution / 5: Substitution / 6: Substitution / 7: Cyclization;

DOI:10.1021/jo991886w

Reference yield:

N,N-diethyl-2,6-dichloro-4-methyl-3-pyridinamide (220559-31-9) → methyl 4.6-dichloro-3-(diethylamino)furo[3,4-c]pyridine-1-carboxylate (220559-34-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 53 percent / LDA; HMPA / tetrahydrofuran / 4 h / -78 - 20 °C

2: 85 percent / p-acetamidobenzenesulfonyl azide; Et₃N / acetonitrile / 12 h / 0 - 20 °C

3: 50 percent / Rh₂(OAc)4 / CH₂Cl₂ / 1 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; 4-acetamidobenzenesulfonyl azide; triethylamine; lithium diisopropyl amide; dirhodium tetraacetate; In tetrahydrofuran; dichloromethane; acetonitrile; 1: Substitution / 2: Substitution / 3: Cyclization;

DOI:10.1021/jo991886w

upstream raw materials:

diazo-(2,6-dichloro-3-diethylcarbamoyl-pyridin-4-yl)-acetic acid methyl ester

2,6-dichloro-4-methylnicotinoyl chloride

2,6-dichloro-4-methylnicotinonitrile

2,6-dichloro-4-methyl-nicotinic acid

Refernces

• 1、 Sarkar, Tarun K.,Ghosh, Sunil K.,Nandy, Sandip K.,Chow, Tahsin J.. "Methyl 4,6-dichloro-3-diethylaminofuro[3,4-c]pyridine-1-carboxylate: Synthesis of the first stable azaisobenzofuran by a Hamaguchi-Ibata reaction". . p. 397 - 398. Retrieved 1999.