반응 #9241

반응 방정식

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

3-aminophenyl boric acid

sodium bicarbonate

boric acid

→

desired compound

수율 23.4%

1-(6-(3-Aminophenyl)-2-benzothiazolyl)-3-ethylurea

수율 23.4%

용매

—

mixed solvent

DMF water

MeOH

반응 조건

후처리

1. 1
   기타was purged with nitrogen gas
2. 2
   기타It was purged with nitrogen gas again
3. 3
   농축concentrated
4. 4
   workup.DISSOLUTIONdissolved in methylene chloride
5. 5
   세척washed with sodium bicarbonate solution
6. 6
   건조dried (MgSO4)
7. 7
   기타evaporated
8. 8
   기타purified by flash chromatography on SiO2 with MeOH and methylene chloride (1/50)

실험 절차

A suspension of 1-(6-bromo-2-benzothiazolyl)-3-ethylurea (0.300 g, 1.00 mmol), 3-aminophenyl boric acid (0.237 g, 1.50 mmol, 1.5 eq), and sodium bicarbonate (0.210 g, 2.50 mmol, 2.5 eq) in 8 mL of mixed solvent DMF/water (5/1) was purged with nitrogen gas. To the mixture, the catalyst Pd(PPh3)4 (0.058 g, 0.05 mmol, 0.05 eq) was added. It was purged with nitrogen gas again, and was heated at about 100° C. in a sealed tube for about 48 hours. More Pd(PPh3)4 (0.025 g, 0.02 mmol, 0.02 eq) and more boric acid (0.080 g, 0.50 mmol, 0.50 eq) were added after the first 24 hours. The mixture was taken up in MeOH, concentrated, dissolved in methylene chloride, washed with sodium bicarbonate solution, dried (MgSO4), evaporated, and purified by flash chromatography on SiO2 with MeOH and methylene chloride (1/50) to give the desired compound 0.073 g (23%). LC/MS 313.2 (M+1); LC retention time 2.11 min.

출처