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

HRID 11152Notes

Reaction equation

HRID 11152 reaction equation
[Br:1][C:2]1[C:10]2[O:9][C:8](/[CH:11]=[CH:12]/[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])=[CH:7][C:6]=2[CH:5]=[C:4]([O:20][CH3:21])[CH:3]=1.[C:22]1(=[O:28])[NH:26][C:25](=[O:27])[CH:24]=[CH:23]1.[Sn](Cl)Cl>>[Br:1][C:2]1[C:10]2[O:9][C:8]3[CH2:11][CH:12]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[Cl:19])[CH:23]4[CH:24]([C:25](=[O:27])[NH:26][C:22]4=[O:28])[C:7]=3[C:6]=2[CH:5]=[C:4]([O:20][CH3:21])[CH:3]=1

Participants

4

Reactant 3

HCID 10935Maleimide2×HCID 24479Stannous Chloride2×HCID 219803277-bromo-2-[(E)-2-(2-chlorophenyl)ethenyl]-5-methoxy-1-benzofuran

Product 1

HCID 219804897-Bromo-4-(2-chlorophenyl)-9-methoxy-3a,4,5,10c-tetrahydro-1H-[1]benzofuro[3,2-e]isoindole-1,3(2H)-dione

Conditions

Temperature
150 °C

Procedure

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.

Workup

  1. temperaturewas again heated to 150° C. overnight
  2. customThe solid which formed
  3. customwas collected
  4. washwashed with xylenes (20 mL)
  5. dissolutionbefore dissolving in ethyl acetate (200 mL)
  6. additionWater (50 mL) was added
  7. filtrationthe mixture was filtered through a pad of Celite
  8. customThe resulting layers were separated
  9. washthe organic phase was washed with brine (50 mL)
  10. dry with materialdried over magnesium sulphate
  11. filtrationfiltered
  12. concentrationconcentrated to dryness
  13. customThe product (860) (6.1 g, 71%) was used without further purification

Sources & evidence

ORD record
ord-2d8a90849f4246fb9111f17d245c4b45
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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