Sodium Iodide → 11-(4S)-[2-(iodomethyldimethylsilanyl)-ethyl]-4-ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione

HRID 2246529Notes

Reaction equation

HRID 2246529 reaction equation
Cl[CH2:2][Si:3]([CH3:33])([CH3:32])[CH2:4][CH2:5][C:6]1[C:18]2[CH2:17][N:16]3[C:11](=[CH:12][C:13]4[C@:23]([CH2:25][CH3:26])([OH:24])[C:22](=[O:27])[O:21][CH2:20][C:14]=4[C:15]3=[O:19])[C:10]=2[N:9]=[C:8]2[CH:28]=[CH:29][CH:30]=[CH:31][C:7]=12.[I-:34].[Na+]>CC(=O)CC>[I:34][CH2:2][Si:3]([CH3:33])([CH3:32])[CH2:4][CH2:5][C:6]1[C:18]2[CH2:17][N:16]3[C:11](=[CH:12][C:13]4[C@:23]([CH2:25][CH3:26])([OH:24])[C:22](=[O:27])[O:21][CH2:20][C:14]=4[C:15]3=[O:19])[C:10]=2[N:9]=[C:8]2[CH:28]=[CH:29][CH:30]=[CH:31][C:7]=12

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 2522749711-(4S)-[2-(chloromethyldimethylsilanyl)-ethyl]-4-ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione

Product 1

HCID 5765938311-(4S)-[2-(iodomethyldimethylsilanyl)-ethyl]-4-ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dioneYield 85%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of Compound 3 (200 mg) and sodium iodide (200 mg) in 2-butanone (4 mL) was heated at 80° C. for 24 hours. Solvent was removed under reduced pressure and directly purified on a silica gel using 1% ethanol in dichloromethane to obtain the required product in 85% yield (200 mg).

Workup

  1. customSolvent was removed under reduced pressure
  2. customdirectly purified on a silica gel using 1% ethanol in dichloromethane

Sources & evidence

ORD record
ord-3262d69a181b4cd2ab26b5c6f5165204
Source dataset
uspto-grants-2010_03
Patent number
US07687496B2

Reaction notes

Loading…