1,2-Dibromoethane → 1'-(diphenylmethyl)-2,3,6,7-tetrahydrospiro[furo[3,2-g]chromene-5,3'-indol]-2'(1'H)-one

HRID 1965442Notes

Reaction equation

[C:1]1([CH:7]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]([C:17]3[C:18]([OH:26])=[CH:19][C:20]4[O:24][CH2:23][CH2:22][C:21]=4[CH:25]=3)[C:9]2=[O:27])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:35][CH2:36]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCCC1>[C:28]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]3([C:17]4[C:18](=[CH:19][C:20]5[O:24][CH2:23][CH2:22][C:21]=5[CH:25]=4)[O:26][CH2:36][CH2:35]3)[C:9]2=[O:27])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of 1-(diphenylmethyl)-3-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-1,3-dihydro-2H-indol-2-one (5.1 g, 11.8 mmol), 1,2-dibromoethane (4.7 g, 25.0 mmol) and cesium carbonate (24.4 g, 75.0 mmol) in tetrahydrofuran (200 mL) was stirred under argon at ambient temperature for 16 h and at 50° C. for 7 h. The reaction mixture was filtered and the filtrate was evaporated under reduced pressure. The residue was subjected to column chromatography with dichlromethane/methanol (100/1-20/1) to afford 1′-(diphenylmethyl)-2,3,6,7-tetrahydrospiro[furo[3,2-g]chromene-5,3′-indol]-2′(1′H)-one (2.11 g, 39%) as a colorless solid: MS (ES+) m/z 459.8 (M+1).

Workup

filtrationThe reaction mixture was filtered
customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record: ord-c2d073f5203f4b15a943608327d868f4
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415370B2

Reaction notes

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