Multi-step reaction with 12 steps
1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 - 20 °C
1.2: 72 h / 0 - 20 °C
2.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / benzene / 5 h / Inert atmosphere; Reflux
3.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C
4.1: pyridine / 4 h / 0 °C
5.1: sulfuric acid; potassium nitrate / 0.45 h / -10 °C
6.1: dihydrogen peroxide; potassium carbonate / water; dimethyl sulfoxide / 20 °C
7.1: toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl acetamide / 20 °C
8.1: sodium nitrite / trifluoroacetic acid / 0.25 h / 0 - 20 °C
9.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C
9.2: 1 h / 0 - 20 °C
10.1: methanol; caesium carbonate / 0.67 h / 0 °C
11.1: toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl acetamide / 2 h / 20 °C
12.1: pyridine / 1 h / 0 °C
With
pyridine; methanol; 2,2'-azobis(isobutyronitrile); sulfuric acid; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium hydride; potassium carbonate; caesium carbonate; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; potassium nitrate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; sodium nitrite;
In
tetrahydrofuran; dichloromethane; N,N-dimethyl acetamide; water; dimethyl sulfoxide; N,N-dimethyl-formamide; trifluoroacetic acid; mineral oil; benzene;
DOI:10.1021/jm201717y