Tributylvinyltin → HCID 68865230, compound

HRID 494099Notes

Reaction equation

HRID 494099 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:11](Br)[N:12]2[CH:17]([CH3:18])[CH2:16][N:15]([CH3:19])[C:14](=[O:20])[C:13]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:27]([Sn](CCCC)(CCCC)C=C)[CH2:28]CC>C1(C)C=CC=CC=1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH2:1]([O:8][C:9]1[C:10]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:11]([CH:27]=[CH2:28])[N:12]2[CH:17]([CH3:18])[CH2:16][N:15]([CH3:19])[C:14](=[O:20])[C:13]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 68864906HCID 68864906, compound

Product 1

HCID 68865230HCID 68865230, compound

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl 8-(benzyloxy)-6-bromo-2,4-dimethyl-1-oxo-1,2,3,4-tetrahydro-pyrrolo[1,2-a]-pyrazine-7-carboxylate (0.5 g, 1.19 mmol), tri-n-butyl vinyltin (0.46 mL, 1.42 mmol), and bis(tri-tert-butylphosphine)palladium(0) (0.12 g, 0.24 mmol) in toluene (6 mL) was purged with nitrogen for 2 minutes and sealed. The mixture was heated in a microwave oven at 100° C. for 10 minutes. The reaction mixture was concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluted with a hexanes and ethyl acetate gradient to provide titled product.

Workup

  1. customwas purged with nitrogen for 2 minutes
  2. customsealed
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. washeluted with a hexanes and ethyl acetate gradient

Sources & evidence

ORD record
ord-46c2719898f74d7f8b28bb475094ccc6
Source dataset
uspto-grants-2009_05
Patent number
US07538112B2

Reaction notes

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