Reacción #11248

Ecuación de reacción

( 859 )

7-Bromo-2-[(E)-2-(2-chlorophenyl)ethenyl]-5-methoxy-1-benzofuran

maleimide

maleimide

tin(II) chloride

tin(II) chloride

→

7-Bromo-4-(2-chlorophenyl)-9-methoxy-3a,4,5,10c-tetrahydro-1H-[1]benzofuro[3,2-e]isoindole-1,3(2H)-dione

Disolventes

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas again heated to 150° C. overnight
2. 2
   OtroThe solid which formed
3. 3
   Otrowas collected
4. 4
   Lavadowashed with xylenes (20 mL)
5. 5
   workup.DISSOLUTIONbefore dissolving in ethyl acetate (200 mL)
6. 6
   workup.ADDITIONWater (50 mL) was added
7. 7
   Filtraciónthe mixture was filtered through a pad of Celite
8. 8
   OtroThe resulting layers were separated
9. 9
   Lavadothe organic phase was washed with brine (50 mL)
10. 10
    Secadodried over magnesium sulphate
11. 11
    Filtraciónfiltered
12. 12
    Concentraciónconcentrated to dryness
13. 13
    OtroThe product (860) (6.1 g, 71%) was used without further purification

Procedimiento

A solution of (859) (4.89 g, 0.0185 mol) prepared as described in example 441, maleimide (1.44 g, 0.02 mol) and tin(II) chloride (2.8 g, 0.02 mol) in xylenes (40 mL) was heated to 150° C. overnight. After the addition of more maleimide (1.44 g, 0.02 mol) and tin(II) chloride (1.44 g, 0.01 mol) the reaction was again heated to 150° C. overnight. The solid which formed was collected and washed with xylenes (20 mL) before dissolving in ethyl acetate (200 mL). Water (50 mL) was added and the mixture was filtered through a pad of Celite. The resulting layers were separated, the organic phase was washed with brine (50 mL) dried over magnesium sulphate, filtered and concentrated to dryness. The product (860) (6.1 g, 71%) was used without further purification. 1H NMR δ (CDCl3) 7.60 (d, J=6.5 Hz, 1H), 7.40 (m, 2H), 7.25 (m, 1H), 7.1 (m, 2H), 4.36 (dd, J=7.3, 1 Hz, 1H), 4.0 (m, 1H), 3.86 (s, 3H), 3.81 (m, 1H), 3.45 (m, 1H), 3.10 (dd, J=4.7, 17 Hz, 1H); MH+:462,460.

Fuente