Multi-step reaction with 9 steps
1: oxalyl dichloride / tetrahydrofuran; N,N-dimethyl-formamide / 0.67 h / Inert atmosphere
2: tetrahydrofuran; N,N-dimethyl-formamide / 1.5 h / Inert atmosphere
3: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 2585.81 Torr
4: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / Inert atmosphere
5: palladium 10% on activated carbon; hydrogen / N,N-dimethyl acetamide / 2068.65 Torr
6: N,N-dimethyl acetamide; 1,2-dichloro-ethane / Inert atmosphere
7: triethylsilane; trifluoroacetic acid / dichloromethane / 0.5 h
8: N,N-dimethyl acetamide; 1,2-dichloro-ethane / Inert atmosphere
9: dmap; N-ethyl-N,N-diisopropylamine / tetrahydrofuran; tetrachloromethane; acetonitrile / Inert atmosphere
With
triethylsilane; dmap; oxalyl dichloride; palladium 10% on activated carbon; hydrogen; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid;
In
tetrahydrofuran; tetrachloromethane; dichloromethane; N,N-dimethyl acetamide; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jm201284m