Dimethylformamide → HCID 20750084, compound

HRID 897284Notes

Reaction equation

HRID 897284 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]([O:15][C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:17])=[C:13]2[C:8]([CH:9]=[CH:10][CH:11]=[N:12]2)=[C:7](I)[N:6]=1)=[O:4].[CH2:25]([OH:28])[C:26]#[CH:27].CN(C=O)C>C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I>[CH3:1][O:2][C:3]([C:5]1[C:14]([O:15][C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:17])=[C:13]2[C:8]([CH:9]=[CH:10][CH:11]=[N:12]2)=[C:7]([C:27]#[C:26][CH2:25][OH:28])[N:6]=1)=[O:4]

Participants

7

Reactant 3

HCID 6228DimethylformamideHCID 7859Propargyl alcoholHCID 22346311HCID 22346311, compound

Product 1

HCID 20750084HCID 20750084, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

A mixture of 5-iodo-8-(1-phenyl-methanoyloxy)-[1,6]naphthyridine-7-carboxylic acid methyl ester (2.00 g, 4.61 mmol), propargyl alcohol (0.563 mL, 9.67 mmol), dichlorobis(triphenylphosphine)palladium(II) (65 mg, 0.092 mmol), and copper iodide (4 mg, 0.023 mmol) were stirred in triethylamine (13 mL) and dry DMF (5 mL) at 30° C. overnight. The solvent was removed in vacuo and the residue was purified by flash chromatography (50-100% EtOAc/Hexane gradient elution switching to 5% MeOH/CH2Cl2) to provide the desired product was a light brown solid.

Workup

  1. customat 30° C.
  2. customovernight
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by flash chromatography (50-100% EtOAc/Hexane gradient elution switching to 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-3344903bce7840f0a9be9fcf7bd8a033
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

Loading…