Tributylvinyltin → HCID 10221196, compound

HRID 365916Notes

Reaction equation

HRID 365916 reaction equation
C([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:16]=[N:17][C:18]([Cl:22])=[C:19](Br)[CH:20]=1)(OC(C)(C)C)=O.[CH:23]([Sn](CCCC)(CCCC)CCCC)=[CH2:24]>C1(C)C=CC=CC=1>[ClH:22].[Cl:22][C:18]1[N:17]=[CH:16][C:15]([O:14][CH2:13][C@@H:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)=[CH:20][C:19]=1[CH:23]=[CH2:24]

Participants

4

Reactant 2

HCID 81998TributylvinyltinHCID 22872668HCID 22872668, compound

Product 1

HCID 10221196HCID 10221196, compoundYield 170%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

3-(1-BOC-2-(S)-pyrrolidinylmethoxy)-5-bromo-6-chloro-pyridine from Example 69a (0.95 g, 2.4 mmol) and tetrakis(triphenylphophino) palladium (0.14 g, 0.12 mmol) were dissolved in toluene (50 mL) and degassed with nitrogen gas for 5 min. Vinyl tributyltin (0.78 mL, 2.67 mmol) was added and the mixture was heated to 90° C. for 1 day. The reaction solvent was evaporated and the crude residue was chromatographed (silica gel; hexanes/EtOAc, 4:1) to provide the title compound (0.69 g, 2.04 mmol, 85%). TLC Rf 0.3 (4:1 hexanes/EtOAc). MS (CI/NH3) m/z 339 (M+H)+. Continued elution provided a minor amount of 5,6-diethenylpyridine (0.044 g, 0.13 mmol, 5.5%): TLC Rf 0.25 (4:1 hexanes/EtOAc); MS (CI/NH3) m/e 331 (M+H)+.

Workup

  1. customdegassed with nitrogen gas for 5 min
  2. customThe reaction solvent was evaporated
  3. customthe crude residue was chromatographed (silica gel; hexanes/EtOAc, 4:1)

Sources & evidence

ORD record
ord-f9a645683f344011924dc6c53a1f95ab
Source dataset
uspto-grants-2000_10
Patent number
US06127386

Reaction notes

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