Dimethylformamide → HCID 22051118, compound

HRID 1831888Notes

Reaction equation

HRID 1831888 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 (200 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-688e4b51daae450ebcd34ea5870023b6
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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