3-amino-6-(3-{[(3-fluorophenyl)amino]carbonyl}phenyl)-N-methylfuro[3,2-b]pyridine-2-carboxamide

Base Information

Chemical Name:3-amino-6-(3-{[(3-fluorophenyl)amino]carbonyl}phenyl)-N-methylfuro[3,2-b]pyridine-2-carboxamide
CAS No.:1314026-69-1
Molecular Formula:C₂₂H₁₇FN₄O₃
Molecular Weight:404.4
Hs Code.:

Synonyms:3-amino-6-(3-{[(3-fluorophenyl)amino]carbonyl}phenyl)-N-methylfuro[3,2-b]pyridine-2-carboxamide

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Chemical Property of 3-amino-6-(3-{[(3-fluorophenyl)amino]carbonyl}phenyl)-N-methylfuro[3,2-b]pyridine-2-carboxamide

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Technology Process of 3-amino-6-(3-{[(3-fluorophenyl)amino]carbonyl}phenyl)-N-methylfuro[3,2-b]pyridine-2-carboxamide

There total 10 articles about 3-amino-6-(3-{[(3-fluorophenyl)amino]carbonyl}phenyl)-N-methylfuro[3,2-b]pyridine-2-carboxamide 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: 54.0%

: 1314026-60-2
ethyl 3-amino-6-(3-{[(3-fluorophenyl)amino]carbonyl}phenyl)furo[3,2-b]pyridine-2-carboxylate

: 74-89-5
methylamine

: 1314026-69-1
3-amino-6-(3-{[(3-fluorophenyl)amino]carbonyl}phenyl)-N-methylfuro[3,2-b]pyridine-2-carboxamide

Guidance literature:: In ethanol; at 110 ℃; for 24h; Inert atmosphere;
DOI:10.1016/j.tet.2011.05.035

Reference yield:

: 286946-77-8
5-bromo-2-chloro-3-hydroxypyridine

: 1314026-69-1
3-amino-6-(3-{[(3-fluorophenyl)amino]carbonyl}phenyl)-N-methylfuro[3,2-b]pyridine-2-carboxamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / Inert atmosphere

1.2: 2 h / 20 °C / Inert atmosphere

2.1: palladium diacetate; sodium carbonate / N,N-dimethyl-formamide / 48 h / 20 °C / Inert atmosphere

3.1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / water; N,N-dimethyl-formamide / 0.3 h / 150 °C / Microwave irradiation; Inert atmosphere

4.1: caesium carbonate / N,N-dimethyl-formamide / 20 h / 80 °C / Inert atmosphere

5.1: triethylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one / N,N-dimethyl-formamide / 48 h / 20 °C / Inert atmosphere

6.1: ethanol / 24 h / 110 °C / Inert atmosphere

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; palladium diacetate; sodium hydride; sodium carbonate; caesium carbonate; triethylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; In ethanol; water; N,N-dimethyl-formamide; mineral oil; 2.1: Suzuki coupling;
DOI:10.1016/j.tet.2011.05.035

Reference yield:

: 552330-34-4
5-bromo-3-(benzyloxy)pyridine N-oxide

: 1314026-69-1
3-amino-6-(3-{[(3-fluorophenyl)amino]carbonyl}phenyl)-N-methylfuro[3,2-b]pyridine-2-carboxamide

Guidance literature:: Multi-step reaction with 8 steps

1.1: trichlorophosphate / dichloromethane / 2 h / Reflux; Inert atmosphere

2.1: hydrogen bromide; acetic acid / 1.5 h / Reflux; Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / Inert atmosphere

3.2: 2 h / 20 °C / Inert atmosphere

4.1: palladium diacetate; sodium carbonate / N,N-dimethyl-formamide / 48 h / 20 °C / Inert atmosphere

5.1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / water; N,N-dimethyl-formamide / 0.3 h / 150 °C / Microwave irradiation; Inert atmosphere

6.1: caesium carbonate / N,N-dimethyl-formamide / 20 h / 80 °C / Inert atmosphere

7.1: triethylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one / N,N-dimethyl-formamide / 48 h / 20 °C / Inert atmosphere

8.1: ethanol / 24 h / 110 °C / Inert atmosphere

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; hydrogen bromide; palladium diacetate; sodium hydride; sodium carbonate; caesium carbonate; acetic acid; triethylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; trichlorophosphate; In ethanol; dichloromethane; water; N,N-dimethyl-formamide; mineral oil; 4.1: Suzuki coupling;
DOI:10.1016/j.tet.2011.05.035