Multi-step reaction with 10 steps
1.1: 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 1.5 h / -15 °C / Inert atmosphere
2.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 0 - 25 °C / Darkness
3.1: iodine; zinc / N,N-dimethyl-formamide / 0.75 h / Inert atmosphere
3.2: 16 h / 60 °C / Inert atmosphere
4.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C
4.2: 6 h / 0 °C
5.1: tetrahydrofuran / -78 - 0 °C / Inert atmosphere
6.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 12 h / 25 °C
7.1: tetrahydrofuran / 0 - 25 °C / Inert atmosphere; Molecular sieve
8.1: pyridinium chlorochromate / dichloromethane / 4 h / 25 °C / Inert atmosphere; Molecular sieve
9.1: 2,6-di-tert-butyl-pyridine / nitromethane / 2 h / -20 °C / Inert atmosphere; Molecular sieve
10.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 12 h / 45 °C / Inert atmosphere
With
4-methyl-morpholine; 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); 2,6-di-tert-butyl-pyridine; iodine; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; pyridinium chlorochromate; zinc;
In
tetrahydrofuran; nitromethane; dichloromethane; N,N-dimethyl-formamide;
9.1: Friedel Crafts acylation / 10.1: Stille coupling;
DOI:10.1021/ja301326k