Dibutyltin oxide → HCID 178492889, compound

HRID 747616Notes

Reaction equation

HRID 747616 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:22][C:23]#[N:24])[S:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=2)(=[O:11])=[O:10])=[C:4]([CH2:25][C:26]2[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:27]=2[F:33])[CH:3]=1.[N:34]([Si](C)(C)C)=[N+:35]=[N-:36].C([Sn](=O)CCCC)CCC>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:22][C:23]2[NH:36][N:35]=[N:34][N:24]=2)[S:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=2)(=[O:11])=[O:10])=[C:4]([CH2:25][C:26]2[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:27]=2[F:33])[CH:3]=1

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 58941232HCID 58941232, compound2×

Product 1

HCID 178492889HCID 178492889, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 8.7 g of N-[4-chloro-2-(2,6-difluorobenzyl)phenyl]-N-(cyanomethyl)-3,4-dimethoxybenzenesulfonamide (compound 211), obtained in Example 18, dissolved in 100 ml of THF are added, at room temperature, 10 g of azidotrimethylsilane and 2.29 g of dibutyltin oxide, and the mixture is refluxed for 8 hours. The reaction medium is concentrated and the residue is chromatographed on a column of silica gel, eluting with a 99/1 (v/v) dichloromethane/methanol mixture to give 7 g of the expected product.

Workup

  1. additionare added, at room temperature
  2. concentrationThe reaction medium is concentrated
  3. customthe residue is chromatographed on a column of silica gel
  4. washeluting with a 99/1 (v/v) dichloromethane/methanol mixture

Sources & evidence

ORD record
ord-cd6c041d58f74a13bfeeebd80f60f25d
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

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