반응 #9220

반응 방정식

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

lithium chloride

triphenylphosphine

tetravinyltin

tin

→

desired compound

수율 39.4%

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

수율 39.4%

용매

MeOH

반응 조건

후처리

1. 1
   기타Similar to the synthesis of Example 203
2. 2
   기타a crystal of 2,6-di-tert-butyl-4-methylphenol was purged with nitrogen gas
3. 3
   여과filtered
4. 4
   농축concentrated
5. 5
   기타Purification by HPLC and flash chromatography on SiO2 with ethyl acetate/methylene chloride (1/4)

실험 절차

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.

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