2-[2-(1H-indol-3-yl)ethyl]-1H-Isoindole-1,3(2H)-dione → 2-[2-(2-bromo-1H-indol-3-yl)-ethyl]-isoindole-1,3-dione

HRID 1458333Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][N:12]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:22])=[CH:2]1.C1C=C[NH+]=CC=1.[Br:29][Br-]Br>O1CCCC1.C(Cl)(Cl)Cl>[Br:29][C:2]1[NH:1][C:9]2[C:4]([C:3]=1[CH2:10][CH2:11][N:12]1[C:13](=[O:22])[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:20]1=[O:21])=[CH:5][CH:6]=[CH:7][CH:8]=2

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-[2-(1H-indol-3-yl)-ethyl]-isoindole-1,3-dione (1.0 g in a mixture of 10 mL dry tetrahydrofuran and 10 mL dry chloroform) at 0° C. was added pyridinium bromide perbromide (1.14 g) and the reaction stirred at 0° C. After 50 minutes, the reaction was quenched by the addition of saturated sodium bicarbonate and extracted with ethyl acetate. The organic portion was washed with saturated sodium bicarbonate (3x) and 0.3M sodium bisulfate (3x) then dried over magnesium sulfate. Purification of the concentrate by flash chromatography on silica gel (hexane:ethyl acetate, 3:1) gave the title compound (1.2 g).

Workup

customthe reaction was quenched by the addition of saturated sodium bicarbonate
extractionextracted with ethyl acetate
washThe organic portion was washed with saturated sodium bicarbonate (3x) and 0.3M sodium bisulfate (3x)
dry with materialthen dried over magnesium sulfate
customPurification of the
concentrationconcentrate by flash chromatography on silica gel (hexane:ethyl acetate, 3:1)

Sources & evidence

ORD record: ord-dba07d8d1aad4aa9b24f664fc1e04c77
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05849764

Reaction notes

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