1-(3-bromophenyl)-1H-pyrrole-2,5-dione → HCID 59540573, compound

HRID 1677548Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12](=[O:13])[CH:11]=[CH:10][C:9]2=[O:14])[CH:5]=[CH:6][CH:7]=1.Br[CH:16]([Si](C)(C)C)[S:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20]>CN(C=O)C.C1C=CC=CC=1.[Cl-].[Na+].O>[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[C:9](=[O:14])[C@H:10]3[C@@H:18]([Si:19]([CH3:22])([CH3:21])[CH3:20])[S:17][CH2:16][C@H:11]3[C:12]2=[O:13])[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A flask was charged with 1-(3-bromo-phenyl)-pyrrole-2,5-dione (800 mg, 3.17 mmol) and bromo-trimethylsilanyl-trimethylsilanylmethylsulfanyl-methane (1.36 g, 4.76 mmol, [literature compound)) in dry DMF (3 ml) under nitrogen atmosphere. The material was heated at 110° C. (oil bath) for 2 hours and then cooled to ambient. The solvent was stripped (rotovap/pump) and the remainder taken up in benzene (30 ml) and brine (30 ml). The material was shaken and the organic phase collected. The aqueous phase was back-extracted with benzene (2×20 ml) and the organic phases combined, dried (MgSO4), filtered and stripped. The crude was purified by chromatography on silica gel eluting with 5% to 40% EtOAc in hexanes, providing 1.04 g of (3S,3aS,6aR)-5-(3-bromo-phenyl)-3-trimethylsilanyl-tetrahydro-thieno[3,4-c]pyrrole-4,6-dione as a light white-yellow solid.

Workup

temperaturecooled
customthe organic phase collected
extractionThe aqueous phase was back-extracted with benzene (2×20 ml)
dry with materialdried (MgSO4)
filtrationfiltered
customThe crude was purified by chromatography on silica gel eluting with 5% to 40% EtOAc in hexanes

Sources & evidence

ORD record: ord-aef610d17dab42ed992d01e9e5f07cf2
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008298B2

Reaction notes

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