Dimethylformamide → HCID 22051118, compound

HRID 1866872Notes

Reaction equation

HRID 1866872 reaction equation
[CH2:1]([N:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:10](I)[C:9]1=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:24]([Sn](CCCC)(CCCC)CCCC)=[CH2:25].CN(C=O)C>C(#N)C>[CH2:1]([N:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:10]([CH:24]=[CH2:25])[C:9]1=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 81998TributylvinyltinHCID 22050830HCID 22050830, compound

Product 1

HCID 22051118HCID 22051118, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 1-benzyl-4-(benzyloxy)-3-iodopyridin-2(1H)-one (1.9 g, 4.56 mmol) and vinyl-tri-butyltin (2.5 mL) in acetonitrile (20 0 mL) containing DMF (2.0 mL) was degassed using house vacuum and purged with argon. Then added PdCl2(PPh3)2 (0.3 g) and the mixture was heated at 65° C. under argon atmosphere for 4 h, with stirring. The solvents were distilled in vacuo, and the residue was triturated with EtOAc and filtered through a pad of celite. The filtrate was concentrated and the residue was purified by silica gel flash chromatography using 25% EtOAc in hexanes to give the title compound (0.75 g. 50%) as an orange colored solid.

Workup

  1. customwas degassed
  2. custompurged with argon
  3. distillationThe solvents were distilled in vacuo
  4. customthe residue was triturated with EtOAc
  5. filtrationfiltered through a pad of celite
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-9a59e92c75ae4ca4a547614bb9b1a18f
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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