反応 #9220

反応方程式

1-(6-bromo-7-trifluoromethylsulfonyl-2-benzothiazolyl)-3-ethylurea

lithium chloride

triphenylphosphine

tetravinyltin

tin

→

desired compound

収率 39.4%

1-(6,7-Di-vinyl-2-benzothiazolyl)-3-ethylurea

収率 39.4%

溶媒

MeOH

反応条件

後処理

1. 1
   その他Similar to the synthesis of Example 203
2. 2
   その他a crystal of 2,6-di-tert-butyl-4-methylphenol was purged with nitrogen gas
3. 3
   ろ過filtered
4. 4
   濃縮concentrated
5. 5
   その他Purification by HPLC and flash chromatography on SiO2 with ethyl acetate/methylene chloride (1/4)

実験手順

Similar to the synthesis of Example 203, a mixture of 1-(6-bromo-7-trifluoromethylsulfonyl-2-benzothiazolyl)-3-ethylurea (0.100 g, 0.22 mmol), lithium chloride (0.078 g, 1.84 mmol, 8.4 eq), triphenylphosphine (0.034 g, 0.13 mmol, 0.6 eq), Pd(PPh3)2Cl2 (0.018 g, 0.026 mmol, 0.12 eq), tetravinyltin (0.080 mL, 0.44 mmol, 2.0 eq), and a crystal of 2,6-di-tert-butyl-4-methylphenol was purged with nitrogen gas, and was heated at about 100° C. for about 18 hours. Additional tin reagent (0.080 mL, 0.44 mmol, 2.0 eq) was added to the mixture after the first 2 hours. The mixture was taken up in MeOH, filtered, and concentrated. Purification by HPLC and flash chromatography on SiO2 with ethyl acetate/methylene chloride (1/4) gave the desired compound 0.014 g (23%). LC/MS 274.3 (M+1); LC retention time 2.32 min.

出典