Magnesium → HCID 25110676, compound

HRID 1873677Notes

Reaction equation

[C:1]1([C:13]2[C:14](=[O:27])[NH:15][CH2:16][C:17]=2[C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][CH:19]=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([C@H:13]2[C@H:17]([C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[NH:20][CH:19]=3)[CH2:16][NH:15][C:14]2=[O:27])[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 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-1,5-dihydro-pyrrol-2-one (700 mg, 2 mmol), MeOH (25 mL) and magnesium turnings (963 mg, 40 mmol) was heated at 60° C. for 4 h. The reaction mixture was then allowed to cool to room temperature and evaporated. The residue was stirred in 1M HCl (70 mL) for 15 mins and extracted twice with EtOAc. The organics were evaporated and the residue purified using column chromatography (SiO2, EtOAc/MeOH). Tituration with hot EtOAc afforded (±)-trans-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-pyrrolidin-2-one as an off-white powder (190 mg, 27%). M.p.=241-243° C.; 1H NMR (400 MHz, DMSO-d6) δ: 10.86 (d, J=1.6 Hz, 1H), 7.92 (s, 1H), 7.44 (d, J=7.6 Hz, 1H), 7.33-7.23 (m, 3H), 7.17 (s, 1H), 7.03 (m, 1H), 6.90 (m, 1H), 6.86-6.78 (m, 2H), 4.03 (m, 4H), 3.81 (m, 1H), 3.31 (m, 1H), 2.87 (t, J=6.4 Hz, 2H), 2.08 (m, 2H); LCMS: 356 [M+H].

Workup

temperatureto cool to room temperature
customevaporated
extractionextracted twice with EtOAc
customThe organics were evaporated
customthe residue purified

Sources & evidence

ORD record: ord-044d1ca3bf594ad787fdc6ca10de1dcb
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304425B2

Reaction notes

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