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With O-phenyl phosphorodichloridate; at 180℃; for 0.5h;
[0658] A suspension of XIII-2 (15 g, 56.4 mmol, 1 eq.) in 35 mL of phenyl dichlorophosphate was heated at 180 C. for 30 minutes whereby a brown solution was obtained. TLC analysis (PE:EA=10:1) showed the reaction completed. The solution was allowed to cool then poured onto ice/water, neutralized by a portionwise addition of solid NaHCO3 and extracted with ethyl acetate (150 mL×3), and then washed with aq. NaHCO3 (5%, 50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to give brown solid. The crude product was purified by flash chromatography on silica gel with petroleum ether/EtOAc (5:1?2:1) to give XIII-3 as yellow solid (14 g, 87% yield). MS (ESI) m/z (M+H)+ 284.7.
87%
With O-phenyl phosphorodichloridate; at 180℃; for 0.5h;
A suspension of XIII-2 (15 g, 56.4 mmol, 1 eq.) in 35 mL of phenyl dichlorophosphate was heated at 180C for 30 minutes whereby a brown solution was obtained. TLC analysis (PE:EA=10:1) showed the reaction completed. The solution was allowed to cool then poured onto ice/water, neutralized by a portionwise addition of solid NaHCO3 and extracted with ethyl acetate (150 mLx3), and then washed with aq. NaHCO3 (5%, 50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to give brown solid. The crude product was purified by flash chromatography on silica gel with petroleum ether/EtOAc (5: 1-*2: 1) to give XIII-3 as yellow solid (14 g, 87% yield). MS (ESI) m/z (M+H) 284.7.
With O-phenyl phosphorodichloridate; at 180℃; for 0.5h;
A suspension of 5-iodo-3-nitro-pyridin-2-ol (20g) in phenyl dichlorophosphate (60ml) was heated at 180 C for 30 minutes whereby a brown solution was obtained. The solution was allowed to cool then poured onto ice/water, neutralised by a portionwise addition of solid sodium hydrogen carbonate and extracted with ethyl acetate (300ml) which was then washed twice with 5% sodium hydrogen carbonate solution (250ml). The organic layer was dried (MgS04), and evaporated to give a pale brown solid. The solid was stirred in isohexane for 2h, filtered off, washed with isohexane and dried to afford the title compound (18.4g). NMR (CDC13) No. 8.49 (1H, d), 8.81 (1H, d). LC/MS t = 2.8min, [M-r] 158 consistent with molecular formula CsH23SCl127IN20z
With O-phenyl phosphorodichloridate; at 180℃; for 0.5h;
A suspension of 5-iodo-3-mtro-2(l//)-py?dmone (4Og) in phenyl dichlorophosphate (80ml) was heated at 1800C for thirty minutes whereby a brown solution was obtained. The solution was allowed to cool then poured onto ice/water and neutralised by a portionwise addition of solid sodium bicarbonate. The aqueous was extracted with ethyl acetate (300ml) which was then washed with 5% sodium bicarbonate solution (2 x 250ml). The organic layer was d?ed (MgSO^, and evaporated to give a pale brown solid. The solid was stirred in iso-hexane for 2h, filtered off, washed with iso-hexane and d?ed at 500C under vacuum to afford the title compound (34. Ig). LC/MS [M-I ] 158 consistent with molecular formula C5H235Cl127IN2O2
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