Technology Process of 5-{[(2,6-difluoro-3,5-dimethoxyphenyl)amino]methyl}-N-ethyl-1H-pyrrolo[2,3-b]pyridin-4-amine
There total 2 articles about 5-{[(2,6-difluoro-3,5-dimethoxyphenyl)amino]methyl}-N-ethyl-1H-pyrrolo[2,3-b]pyridin-4-amine which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
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Multi-step reaction with 4 steps
1.1: sodium hydride; pyridine / mineral oil / 1 h / 0 - 20 °C / Inert atmosphere; Large scale
1.2: 20 h / 20 - 25 °C / Large scale
2.1: sec.-butyllithium / cyclohexane / 0.8 h / -75 - -60 °C / Inert atmosphere; Large scale
2.2: 0.5 h / -75 - -65 °C / Large scale
2.3: 20 - 25 °C / Large scale
3.1: water; 2-methoxy-ethanol / 130 °C
4.1: (1S)-10-camphorsulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 48 h / Reflux; Dean-Stark
4.2: 3 h / 50 °C
With
pyridine; (1S)-10-camphorsulfonic acid; sec.-butyllithium; sodium hydride;
In
5,5-dimethyl-1,3-cyclohexadiene; 2-methoxy-ethanol; cyclohexane; water; mineral oil;
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 4.5 h / 50 - 65 °C / Large scale
2.1: methanol / 21 h / 20 - 70 °C / Inert atmosphere; Large scale
2.2: 1 h / Large scale
3.1: 75 - 85 °C / Inert atmosphere; Large scale
4.1: palladium on activated charcoal; ammonium formate; acetic acid / ethanol / 50 °C / Large scale
5.1: (1S)-10-camphorsulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 48 h / Reflux; Dean-Stark
5.2: 3 h / 50 °C
With
methanol; palladium on activated charcoal; (1S)-10-camphorsulfonic acid; ammonium formate; acetic acid; N-ethyl-N,N-diisopropylamine;
In
1-methyl-pyrrolidin-2-one; 5,5-dimethyl-1,3-cyclohexadiene; ethanol;
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: tetrahydrofuran / 6 h / 0 - 20 °C
2.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C
2.2: 1.5 h / 0 °C
3.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C
3.2: 0.5 h / -78 °C
4.1: acetic acid / dichloromethane / 20 °C
4.2: 3 h / 20 °C
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 50 °C
With
tetrabutyl ammonium fluoride; sodium hydride; acetic acid; lithium diisopropyl amide;
In
tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; mineral oil;
