Magnesium → HCID 59408999, compound

HRID 1894727Notes

Reaction equation

HRID 1894727 reaction equation
[C:1]1([CH2:13][C:14]2[C:15](=[O:29])[NH:16][C:17](=[O:28])[C:18]=2[C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:21][CH:20]=2)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[CH:2]=1.[Mg]>CO>[C:1]1([CH2:13][C@H:14]2[C@H:18]([C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[NH:21][CH:20]=3)[C:17](=[O:28])[NH:16][C:15]2=[O:29])[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[CH:2]=1

Participants

4

Reactant 2

HCID 5462224MagnesiumHCID 59408988HCID 59408988, compound

Product 1

HCID 59408999HCID 59408999, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-ylmethyl)-4-(1H-indol-3-yl)-pyrrole-2,5-dione (207 mg, 0.54 mmol) in anhydrous methanol (12 ml) was added magnesium turnings (264 mg, 10.7 mmol). The mixture was heated to reflux for 1.5 hours. The mixture was separated between ethyl acetate (200 ml) and water (600 ml), the organic layer dried over anhydrous magnesium sulfate and evaporated to dryness to give a pale yellow brown solid. The solid was triturated with methanol and the solids filtered off and washed with ice cold methanol to yield (±)-trans-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-ylmethyl)-4-(1H-indol-3-yl)-pyrrolidine-2,5-dione as an off white powder (83 mg). M.p.=215-218° C.; 400 MHz 1H NMR (DMSO-d6) δ: 11.28 (s, 1H), 11.00 (s, 1H), 7.35-6.75 (m, 9H), 4.07 (m, 2H), 3.98 (d, J=5.2 Hz, 1H), 3.26-3.16 (m, 3H), 2.89 (m, 2H), 2.09 (m, 2H); LCMS: 384 [M+H].

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1.5 hours
  3. customThe mixture was separated between ethyl acetate (200 ml) and water (600 ml)
  4. dry with materialthe organic layer dried over anhydrous magnesium sulfate
  5. customevaporated to dryness
  6. customto give a pale yellow brown solid
  7. customThe solid was triturated with methanol
  8. filtrationthe solids filtered off
  9. washwashed with ice cold methanol

Sources & evidence

ORD record
ord-cf28f924828e4ea2bebfff0775e8ee0a
Source dataset
uspto-grants-2013_08
Patent number
US08513292B2

Reaction notes

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