HCID 59408985, compound → HCID 59409006, compound

HRID 1894733Notes

Reaction equation

HRID 1894733 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[C:11](=[O:28])[NH:12][C:13](=[O:27])[C:14]=2[C:15]2[CH:16]=[C:17]3[C:22]4=[C:23]([CH2:25][CH2:26][N:21]4[CH2:20][CH2:19][CH2:18]3)[CH:24]=2)=[CH:2]1>ClCCl.[O-2].[O-2].[Mn+4]>[CH:25]1[C:23]2=[C:22]3[C:17](=[CH:16][C:15]([C:14]4[C:13](=[O:27])[NH:12][C:11](=[O:28])[C:10]=4[C:3]4[C:4]5[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=5)[NH:1][CH:2]=4)=[CH:24]2)[CH2:18][CH2:19][CH2:20][N:21]3[CH:26]=1

Participants

4

Reactant 1

HCID 59408985HCID 59408985, compound

Product 1

HCID 59409006HCID 59409006, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(1H-indol-3-yl)-4-(1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-8-yl)-pyrrole-2,5-dione (90 mg) in dichloromethane (10 ml) at room temperature was treated with manganese dioxide (300 mg; ca. 85%, 5 μm, activated) and stirred for 1 hour. The reaction mixture was filtered through a bed of celite and the filter cake was washed with methanol (15 ml). The filtrate was evaporated to dryness and 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-8-yl)-4-(1H-indol-3-yl)-pyrrole-2,5-dione (88 mg) was used without further purification. 400 MHz 1H NMR (CDCl3) δ: 8.65 (s, 1H), 7.92 (d, J=2.4 Hz, 1H), 7.73 (d, J=1.6 Hz, 1H), 7.51 (s, 1H), 7.33 (d, J=8.4 Hz, 1H), 7.07 (m, 2H), 6.70 (t, J=8.0 Hz, 1H), 6.57 (d, J=8.0 Hz, 1H), 6.38 (d, J=3.2 Hz, 1H), 4.13 (m, 2H), 2.79 (t, J=6.4 Hz, 2H), 2.16 (m, 2H); LCMS: 368 [M+H].

Workup

  1. filtrationThe reaction mixture was filtered through a bed of celite
  2. washthe filter cake was washed with methanol (15 ml)
  3. customThe filtrate was evaporated to dryness and 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-8-yl)-4-(1H-indol-3-yl)-pyrrole-2,5-dione (88 mg)
  4. customwas used without further purification

Sources & evidence

ORD record
ord-3752549143434efd9d0725f1fc435efc
Source dataset
uspto-grants-2013_08
Patent number
US08513292B2

Reaction notes

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