After putting DMF (350 ml), Sub1-I-34 (32.4 g, 107 mmol) and NBS (20.0 g, 112 mmol) in a round bottom flask, the mixture was stirred for 8 hours. The reaction-terminated solution was washed with water, extracted with methylene chloride and concentrated. After the intermediate was dissolved in NMP (350 ml), K2CO3 (28.1 g, 203 mmol) was added and the mixture was stirred for 3 hours under reflux. The reaction-terminated solution was washed with water, extracted with methylene chloride and concentrated. Thereafter, the concentrate was recrystallized using toluene to obtain 27 g of Compound Sub 1-II-34. (yield: 70%)
(3) Synthesis of Sub1-34
After putting Sub1-II-34 (27 g, 74.9 mmol), diphenylamine (25.4 g, 150 mmol), Pd2(dba)3 (2.06 g, 2.25 mmol), P(t-Bu)3 (50 wt % Sol.) (1.82 mL, 4.49 mmol) and t-BuONa (14.4 g, 150 mmol) in a round bottom flask, anhydrous toluene (250 mL) was added thereto and the reaction was carried out for 2 hours. When the reaction was completed, the reaction product was separated by column chromatography to obtain 20.5 g of Compound Sub 1-34. (yield: 51%)