potassium carbonate in tert-butyl methyl ether; N,N-dimethyl-formamide T=20°C; 16 h;

toluene-4-sulfonic acid in methanol

caesium carbonate in N,N-dimethyl-formamide 3 h;

sulfuric acid 1 h; Reflux;

hydrogenchloride; sodium borohydride; aluminium trichloride in diethylene glycol dimethyl ether

1: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene; caesium carbonate / 90 °C / |Sealed tube; |Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 3: pyridine / dichloromethane / 20 °C 4: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 20 °C / |Cooling with ice 5: N-bromosuccinmide / N,N-dimethyl acetamide / 0.25 h / 20 °C 6: N,N-dimethyl acetamide / 20 - 60 °C 7: N,N-dimethyl acetamide / 60 - 80 °C 8: ammonia / methanol / 24 h / 90 °C / |Sealed tube View Scheme

1: With carbamic acid 1,1-dimethylethyl ester; caesium carbonate; 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene; tris(dibenzylideneacetone)dipalladium(0) chloroform complex in toluene T=90°C; Inert atmosphere; 2: With trifluoroacetic acid in dichloromethane T=20°C; 1 h; Inert atmosphere;