Multi-step reaction with 10 steps
1.1: carbon tetrabromide; triphenylphosphine / pyridine / 1.17 h / 65 °C / Inert atmosphere; Cooling with ice
2.1: N-ethyl-N,N-diisopropylamine; piperidine / N,N-dimethyl-formamide / 0.75 h / 60 °C / Inert atmosphere
3.1: pyridine / 17 h / 20 °C / Inert atmosphere; Cooling with ice
4.1: methylhydrazine; caesium carbonate / N,N-dimethyl-formamide / 0.42 h / 20 °C / Inert atmosphere
5.1: sodium methylate; methanol / 44 h / 20 °C / Inert atmosphere
6.1: dichloromethane / 2 h / 20 °C / Inert atmosphere; Molecular sieve
6.2: 14 h / 0 °C / Inert atmosphere; Molecular sieve
7.1: trifluoroacetic acid / dichloromethane / 1.25 h / -20 °C / Inert atmosphere
8.1: pyridine / 14 h / 60 °C / Inert atmosphere; Cooling with ice
9.1: trifluoroacetic acid / dichloromethane / 0.67 h / 20 °C / Inert atmosphere; Cooling with ice
10.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
With
piperidine; pyridine; methanol; carbon tetrabromide; sodium methylate; caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; triphenylphosphine; methylhydrazine; trifluoroacetic acid;
In
pyridine; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2014.02.023