Boron tribromide → 2a-[4-(6-Hydroxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-2-yl)-butyl]-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one

HRID 2301075Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]1[CH2:12][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][C:20]34[CH2:31][CH2:30][CH2:29][C:27]5[C:28]3=[C:23]([CH:24]=[CH:25][CH:26]=5)[NH:22][C:21]4=[O:32])[CH2:14][CH2:15][C:6]2=1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]1[CH2:12][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][C:20]34[CH2:31][CH2:30][CH2:29][C:27]5[C:28]3=[C:23]([CH:24]=[CH:25][CH:26]=5)[NH:22][C:21]4=[O:32])[CH2:14][CH2:15][C:6]2=1

Participants

Conditions

Temperature: 0 °C

Procedure

A 1.3 ml portion of dichloromethane solution containing 68 mg (0.16 mmol) of 2a-[4-(6-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-2-yl)butyl]-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one was cooled to 0° C. and mixed with 0.2 ml of dichloramethane solution containing 45 μl (0.48 mmol) of boron tribromide. After 6 hours of stirring at room temperature, the reaction solution was extracted with a solution of chloroform-methanol=5:1 and washed with sodium bicarbonate aqueous solution. After drying (Na2SO4), the solvent was removed by evaporation under a reduced pressure and the residue was recrystallized from methanol-ethyl acetate to obtain 20 mg of the title compound (30% in yield).

Workup

additionmixed with 0.2 ml of dichloramethane solution
extractionthe reaction solution was extracted with a solution of chloroform-methanol=5:1
washwashed with sodium bicarbonate aqueous solution
dry with materialAfter drying (Na2SO4)
customthe solvent was removed by evaporation under a reduced pressure
customthe residue was recrystallized from methanol-ethyl acetate

Sources & evidence

ORD record: ord-0a4dc81505af412ba65c1dbfc384a144
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06498251B1

Reaction notes

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