Tributylvinyltin → tert-butyl N-[4-(methanesulfonylamino)-3-vinylbenzyl]carbamate

HRID 2358412Notes

Reaction equation

HRID 2358412 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:20]=[CH:19][C:9]([CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:8][C:7]=1I)(=[O:4])=[O:3].[CH2:22]([Sn](CCCC)(CCCC)C=C)[CH2:23]CC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][S:2]([NH:5][C:6]1[CH:20]=[CH:19][C:9]([CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:8][C:7]=1[CH:22]=[CH2:23])(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 69467623tert-Butyl N-[4-(methanesulfonylamino)-3-iodobenzyl]carbamate

Product 1

HCID 68453842tert-butyl N-[4-(methanesulfonylamino)-3-vinylbenzyl]carbamateYield 98.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

tert-Butyl N-[4-(methanesulfonylamino)-3-iodobenzyl]carbamate (1.0 g, 2.3 mmol) was dissolved in toluene (20 mL). Tributyl vinyltin (0.8 mL, 2.8 mmol) and Pd(PPh3)4 (140 mg, 0.12 mmol) were dropwisely added. The reaction mixture was stirred for 4 hrs in reflux. Toluene was removed in vacuo. The residue was extracted with EtOAc. A combined organic layer was washed with H2O, brine, dried over MgSO4, and concentrated in vacuo. The residue was purified with column chromatography (EtOAc: n-hexane=1:2) to yield title compound (740 mg, 97%).

Workup

  1. temperaturein reflux
  2. customToluene was removed in vacuo
  3. extractionThe residue was extracted with EtOAc
  4. washA combined organic layer was washed with H2O, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified with column chromatography (EtOAc: n-hexane=1:2)

Sources & evidence

ORD record
ord-0df898b22c684c2fa82495329b3db3ad
Source dataset
uspto-grants-2010_07
Patent number
US07763657B2

Reaction notes

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