Hydrochloric Acid → 4-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-3-(1H-indol-3-yl)-pyrrolidin-2-one

HRID 1873672Notes

Reaction equation

[C:1]1([C:13]2[CH2:17][NH:16][C:15](=[O:18])[C:14]=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.Cl>CCOC(C)=O.O>[C:1]1([CH:13]2[CH2:17][NH:16][C:15](=[O:18])[CH:14]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

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 4-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-3-(1H-indol-3-yl)-1,5-dihydro-pyrrol-2-one (95 mg, 270 μmol), magnesium turnings (1.3 g, 54 mmol) and methanol (15 mL) was heated at 60° C. for 3 h. Water was added to the reaction mixture and the pH adjusted to 1 with concentrated HCl. The mixture was extracted into EtOAc and washed with saturated sodium carbonate solution. The organics were dried (MgSO4), filtered and evaporated to yield a tan solid, which was titurated in hot EtOAc, yielding 4-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-3-(1H-indol-3-yl)-pyrrolidin-2-one as a white solid (15 mg, 16%, cis/trans: 1/3.7 from 1H NMR). 1H NMR (400 MHz, CD3OD) trans-δ: 7.42 (d, J=7.2 Hz, 1H), 7.33 (d, J=8.0 Hz, 1H), 7.14 (d, J=8.0 Hz, 1H), 7.06 (m, 1H), 7.00 (s, 1H), 6.95 (s, 1H), 6.93 (m, 1H), 6.82 (m, 2H), 4.14-4.05 (m, 4H), 3.85 (m, 1H), 3.71 (m, 1H), 2.90 (t, J=6.0 Hz, 2H), 2.12 (m, 2H). LCMS: m/e 356.13 [M+H].

Workup

extractionThe mixture was extracted into EtOAc
washwashed with saturated sodium carbonate solution
dry with materialThe organics were dried (MgSO4)
filtrationfiltered
customevaporated
customto yield a tan solid, which

Sources & evidence

ORD record: ord-785f2c5bc8d747a2b1d2e08e3f9e8633
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304425B2

Reaction notes

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