Multi-step reaction with 11 steps
1.1: 67 percent / PPh3; imidazole; I2 / CH2Cl2 / 2 h / 20 °C
2.1: 91 percent / nitromethane / Heating
3.1: n-BuLi / diethyl ether / 1 h / 20 °C
3.2: 56 percent / diethyl ether / -78 - 20 °C
4.1: 9-BBN / tetrahydrofuran / 5 h / 0 - 20 °C
4.2: 63 percent / Cs2CO3; AsPh3; Pd(dppf)Cl2*CH2Cl2 / tetrahydrofuran; dimethylformamide; H2O / 20 - 75 °C
5.1: 94 percent / aq. K2CO3 / methanol
6.1: 81 percent / BF3*OEt2 / CHCl3 / 48 h / 20 °C
7.1: 100 percent / CF3SO3H / diethyl ether / 0.33 h / 0 °C
8.1: 78 percent / dimethylsulfoxide; dimethylformamide / 72 h
9.1: 100 percent / K2CO3 / methanol
10.1: POCl3; Et3N / CHCl3 / -10 - 20 °C
10.2: 84 percent / pyridine / CHCl3 / 48 h / 20 °C
11.1: 65 percent / aq. DDQ / CH2Cl2 / 20 °C
With
1H-imidazole; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; iodine; potassium carbonate; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; trichlorophosphate;
In
tetrahydrofuran; methanol; diethyl ether; nitromethane; dichloromethane; chloroform; dimethyl sulfoxide; N,N-dimethyl-formamide;