2-Methoxypyridine → (4S)-11-{2-[dimethyl-(2-oxo-2H-pyridin-1-ylmethyl)-silanyl]-ethyl}-4-ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione

HRID 2246546Notes

Reaction equation

HRID 2246546 reaction equation
I[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.C[O:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=1>CN(C)C=O>[CH3:32][Si:3]([CH3:33])([CH2:2][N:37]1[CH:38]=[CH:39][CH:40]=[CH:41][C:36]1=[O:35])[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 742012-MethoxypyridineHCID 5765938311-(4S)-[2-(iodomethyldimethylsilanyl)-ethyl]-4-ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione

Product 1

HCID 25261404(4S)-11-{2-[dimethyl-(2-oxo-2H-pyridin-1-ylmethyl)-silanyl]-ethyl}-4-ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dioneYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Compound 4 (60 mg) and 2-methoxypyridine (0.11 mL) in N,N-dimethylformamide (1 mL) was heated at 70° C. for 16 hours. The reaction mixture was concentrated under vacuum and the residue was directly eluted on a silica gel column using 4% ethanol in dichloromethane to obtain the required product in 44% yield (25 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. washthe residue was directly eluted on a silica gel column

Sources & evidence

ORD record
ord-56681430f3fd4ca9ad5eff8ee2ed53da
Source dataset
uspto-grants-2010_03
Patent number
US07687496B2

Reaction notes

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