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90-5.83 (m, 1H, Angew. Chem. Int. Ed, vol.3967, issue.3, pp.4156-4158, 2000. ,
CDCl 3 , 100.6 MHz): ? 161.0 (C A ) ,
07-1.97 (m, 1H, pp.95-98 ,
CDCl 3 , 100.6 MHz): ? 171 ,
05-1.95 (m, 1H, H 2 ), 1.57-1.50 (m, 1H, pp.3042-3043 ,
CDCl 3 , 100.6 MHz): ? 171 ,
CDCl 3 , 100.6 MHz): ? 171.0 (C A ) ,
77 (d, J = 8, pp.6-9995 ,
CDCl 3 , 75 MHz): ? 169 ,
CDCl 3 , 100.6 MHz): ? 170.2 (C A ) ,
CDCl 3 , 100.6 MHz): ? 169 ,
73 (s, 3H, H 12, 1H, H 9 ), 4.23 (dd, J = 14.6, 5.8 Hz, 1H 1H, H 5 ), 2.18-2.16 (m, 1H 0.92 (d, J = 6.2 Hz, 3H, pp.5-7 ,
6 MHz): ? 172.6 (C A ) ,
72 (s, 3H, H 13 ), 3.60 (br s, 1H, H 7 ), 3.57 (d, J = 4, pp.4-257961, 2007. ,
CDCl 3 , 100.6 MHz): ? 170.1 (C A ) ,
41 (s, 1H, H 1 ), 4.34 (dd, 2H, H 3 ), 6.78 (d, J = 8.0 Hz, 2H, H 9 ), 6.52 (d, J = 8.0 Hz, pp.38-45, 2008. ,
CDCl 3 , 100.6 MHz): ? 171 ,
The crude product was purified by flash column chromatography on silica gel (petroleum ether : diethyl ether 50 : 50) to obtain the desired product as a white solid ,
12 (br s, 1H, pp.61-62 ,
CDCl 3 , 100.6 MHz): ? 169.2 (C A ) ,
CDCl 3 , 100.6 MHz): ? 169 ,
CDCl 3 , 100.6 MHz): ? 173 ,
82 (s, 3H, H 9 ), 3.22-3.12 (m, 2H, H 5 ) 13 C NMR (CDCl 3 , 100.6 MHz): ? 169 ,
CDCl 3 , 100.6 MHz): ? 173 ,
CDCl 3 , 100.6 MHz): ? 169 ,
5 (C 5 ). 6.33 -N -cyclopropyl-2-iodoaniline A solution of Cu(OAc) 2 (200 mg, 1 mmol) and bipyridine (156 mg, 1 mmol) in dichloroethane (8.3 mL, 0.12 M) at 70°C was added to a room temperature suspension of the 2-iodoaniline (219 mg, 1mmol), cyclopropylboronic acid (172 mg, 2 mmol) and Na 2 CO 3 (212 mg ,
The mixture was heated at 70°C until the reaction was judged to be complete by TLC (2-3 hours) After cooling to room temperature, an aqueous solution of NH 4 OH (25%) was added. The organic layer was separated and 7, mmol) in dichloroethane (1.6 mL, pp.4-45 ,
CDCl 3 , 100.6 MHz): ? 154 ,
The mixture was heated at 70°C until the reaction was judged to be complete by TLC (1 hour) After cooling to room temperature, an aqueous solution of NH 4 OH (25%) was added. The organic layer was separated and the aqueous layer was extracted three times with dichloromethane. The combined yellow Hz, mmol) in dichloroethane (1.6 mL, pp.78-758 ,
18-1.92 (m, 3H, pp.9490-9493 ,
CDCl 3 , 100.6 MHz): ? 172 ,