Cesium carbonate → tert-Butyl 2-(7-(3,4-Diethoxybenzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

HRID 1964144Notes

Reaction equation

[OH:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:11][CH2:12][CH:13]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:6]3=[CH:5][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH3:38])=[C:32]([O:39][CH2:40][CH3:41])[CH:31]=1>CC(N(C)C)=O>[CH2:40]([O:39][C:32]1[CH:31]=[C:30]([CH:35]=[CH:34][C:33]=1[O:36][CH2:37][CH3:38])[CH2:29][O:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:11][CH2:12][CH:13]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:6]3=[CH:5][C:4]=2[CH:3]=1)[CH3:41]

Participants

Conditions

Temperature: 60 °C

Procedure

tert-Butyl 2-(7-hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (0.150 g, 0.522 mmol), cesium carbonate (0.255 g, 0.783 mmol) and 4-(chloromethyl)-1,2-diethoxybenzene (0.168 g, 0.783 mmol) were taken up in DMA (2 mL) and heated to 60° C. for 16 h in a 20 mL sealed scintillation vial. The mixture was cooled down to room temperature and filtered by vacuum filtration through a glass fiber paper. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (173.1 mg).

Workup

customsealed scintillation vial
temperatureThe mixture was cooled down to room temperature
filtrationfiltered by vacuum filtration through a glass fiber paper
customThe solvent was removed under reduced pressure
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-0186dd96abe54105aad116197aa984ab
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415484B2

Reaction notes

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