Multi-step reaction with 11 steps
1.1: aq. HCl / acetonitrile / 1 h / 20 °C
2.1: 2.49 g / Et3N; HOBT; EDCI / dimethylformamide / 17 h / 20 °C
3.1: 251 mg / TBAF; 3 Angstroem molecular sieves / dimethylsulfoxide; tetrahydrofuran / 20 h / 60 °C
4.1: H2 / Pd/C / ethyl acetate; methanol / 2.5 h / 20 °C
5.1: 32.6 mg / aq. H3PO2; NaNO2; Cu2O / SnCl2 / tetrahydrofuran / 4 h / 0 - 20 °C
6.1: 82 percent / H2 / Pd/C / methanol / 72 h / 20 °C
7.1: 87 percent / DIEA; HATU / dimethylformamide / 17 h / 20 °C
8.1: Et3n / CH2Cl2 / 1 h / -15 °C
9.1: NaBH4 / ethanol / 0 °C
9.2: 55 mg / ethanol / 2 h / 80 °C
10.1: pyridine; aq. H2O2 / CH2Cl2 / 1.33 h / 0 - 20 °C
11.1: 8.5 mg / benzene / 2 h / 60 °C
With
pyridine; copper(I) oxide; hydrogenchloride; sodium tetrahydroborate; 3 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; hypophosphorous acid; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium nitrite;
palladium on activated charcoal; tin(ll) chloride;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1002/chem.200401070