Technology Process of (S)-6-bromo-N-(3-(1-methyl-1H-pyrazol-4-yl)-5-(1-methylpyrrolidin-3-yloxy)phenyl)quinazolin-2-amine
There total 8 articles about (S)-6-bromo-N-(3-(1-methyl-1H-pyrazol-4-yl)-5-(1-methylpyrrolidin-3-yloxy)phenyl)quinazolin-2-amine which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
C23H21BrN6O;
With
sodium triacetoxy borohydride;
In
methanol; water;
for 0.5h;
With
water;
In
methanol;
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: boron tribromide / dichloromethane / 20 °C / Cooling with ice bath
1.2: -78 - 20 °C
2.1: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran; water / 1.5 h / 80 °C
3.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0.33 h / 20 °C
3.2: 15 h
4.1: hydrogen / palladium 10% on activated carbon / methanol / 17 h / 20 °C / 760.05 Torr / Inert atmosphere of argon
5.1: isopropyl alcohol / 16 h / 100 °C
6.1: trifluoroacetic acid / dichloromethane / 0.25 h
6.2: pH ~ 11
7.1: acetic acid / methanol; water / 0.75 h / 20 °C
8.1: sodium triacetoxy borohydride / methanol; water / 0.5 h
With
sodium triacetoxy borohydride; hydrogen; boron tribromide; sodium carbonate; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate;
dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; palladium 10% on activated carbon; acetic acid;
In
tetrahydrofuran; methanol; dichloromethane; water; isopropyl alcohol;
2.1: Suzuki Coupling / 3.1: Mitsunobu reaction / 3.2: Mitsunobu reaction;
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0.33 h / 20 °C
1.2: 15 h
2.1: hydrogen / palladium 10% on activated carbon / methanol / 17 h / 20 °C / 760.05 Torr / Inert atmosphere of argon
3.1: isopropyl alcohol / 16 h / 100 °C
4.1: trifluoroacetic acid / dichloromethane / 0.25 h
4.2: pH ~ 11
5.1: acetic acid / methanol; water / 0.75 h / 20 °C
6.1: sodium triacetoxy borohydride / methanol; water / 0.5 h
With
sodium triacetoxy borohydride; hydrogen; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate;
palladium 10% on activated carbon; acetic acid;
In
tetrahydrofuran; methanol; dichloromethane; water; isopropyl alcohol;
1.1: Mitsunobu reaction / 1.2: Mitsunobu reaction;