Tri(butyl)vinyltin → HCID 68456961, compound

HRID 2358416Notes

Reaction equation

HRID 2358416 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][C:9]1[CH:14]=[C:13](I)[C:12]([NH2:16])=[CH:11][C:10]=1[O:17][CH3:18])([CH3:4])([CH3:3])[CH3:2].[CH2:20](C([Sn])=C(CCCC)CCCC)[CH2:21]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>[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([CH:20]=[CH2:21])[C:12]([NH2:16])=[CH:11][C:10]=1[O:17][CH3:18])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 53438229Tri(butyl)vinyltinHCID 68454768HCID 68454768, compound

Product 1

HCID 68456961HCID 68456961, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a solution of (4-amino-5-iodo-2-methoxy-benzyl)-carbamic acid tert-butyl ester (700 mg, 1.85 mmol) and tributylvinyltin (783 mg, 2.68 mmol) in toluene was added Pd(PPh3)4 (214 mg, 0.19 mmol) under argon. The resulting mixture was heated with reflux for 8 hrs, filtered through celite, and then concentrated under reduced pressure. The crude residue was column-chromatographed (hexane/ethylacetate=2/1 to 1/1) to yield (4-amino-2-methoxy-5-vinyl-benzyl)-carbamic acid tert-butyl ester (220 mg, 43%).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperaturewith reflux for 8 hrs
  3. filtrationfiltered through celite
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue was column-chromatographed (hexane/ethylacetate=2/1 to 1/1)

Sources & evidence

ORD record
ord-61f3831ae69d49e1a711d09daa74c42f
Source dataset
uspto-grants-2010_07
Patent number
US07763657B2

Reaction notes

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