反应详情

温度

-10 °C

5-Hydroxyindole (91.8 g, 0.69 mol) is added in portions to a stirred solution of NaOH (27.9 g, 0.69 mol) in water (560 m L) at 10° C., to give a solution which is then cooled to −10° C. A solution of 4,6-dichloropyrimidine (95.3 g, 0.63 mol) in acetone (560 mL) is then added over a period of 65 min. The mixture is stirred at 0° C. for 30 min and then the acetone is evaporated off under reduced pressure, to give a mixture which is extracted with CH2Cl2. The combined extracts are washed with cold aqueous NaOH (0.5 M), dried (Na2SO4) and the solvent is evaporated off under reduced pressure to afford the product to afford the crude product which is purified by chromatography (silica gel; eluent 10% EtOAc in CH2Cl2) and recrystallised from CH2Cl2—hexane to give the title compound as a colourless crystalline solid, m.p. 149-150° C. Utilising a similar procedure, but employing 2,4-dichloropyrimidine in lieu of 4,6-dichloropyrimidine afforded 5-[(2-chloro-4-pyrimidinyl)oxy]-1H-indole, as cream crystalline solid, m.p. 169-176° C.

1. customto give a solution which
2. customthe acetone is evaporated off under reduced pressure
3. customto give a mixture which
4. extractionis extracted with CH2Cl2
5. washThe combined extracts are washed with cold aqueous NaOH (0.5 M)
6. dry with materialdried (Na2SO4)
7. customthe solvent is evaporated off under reduced pressure
8. customto afford the product
9. customto afford the crude product which
10. customis purified by chromatography (silica gel; eluent 10% EtOAc in CH2Cl2)
11. customrecrystallised from CH2Cl2—hexane