Dibutyltin oxide → HCID 21886449, compound

HRID 723141Notes

Reaction equation

HRID 723141 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[N:17].[N:18]([Si](C)(C)C)=[N+:19]=[N-:20].C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[N:17]1[NH:18][N:19]=[N:20][C:16]=1[CH2:15][CH2:14][CH2:13][CH2:12][N:3]1[C:4](=[O:11])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]1=[O:1]

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 227606STK366373

Product 1

HCID 21886449HCID 21886449, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pentanenitrile (6.84 g, 30 mmol) and azidotrimethylsilane (14 mL, 108 mmol) in toluene (40 mL) was added dibutyltin oxide (2.1 g, 6.0 mmol). The mixture was heated at 100° C. for 48 h, concentrated, and flash chromatographed on silica gel column, eluting with EtOAc/DCM (30 and 60%) followed by methanol/DCM (2.5 and 5%) to give the title compound (6.72 g, 83% yield) as a white solid.

Workup

  1. concentrationconcentrated
  2. customflash chromatographed on silica gel column
  3. washeluting with EtOAc/DCM (30 and 60%)

Sources & evidence

ORD record
ord-6cc76dca9388426fa4b01a6b64003304
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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