Propargyl alcohol → HCID 16073845, compound

HRID 1067977Notes

Reaction equation

HRID 1067977 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16](I)[CH:17]=3)[N:12]([CH:22]3[CH2:24][CH2:23]3)[CH:11]=2)=[O:9])=[CH:4][CH:3]=1.C(NCC)C.[CH2:32]([OH:35])[C:33]#[CH:34]>CN(C=O)C.[Cu]I.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>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:34]#[C:33][CH2:32][OH:35])[CH:17]=3)[N:12]([CH:22]3[CH2:24][CH2:23]3)[CH:11]=2)=[O:9])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 7859Propargyl alcoholHCID 8021DiethylamineHCID 21192589HCID 21192589, compound

Product 1

HCID 16073845HCID 16073845, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a dry flask under an atmosphere of argon gas containing 0.24 g of N-(4-chlorobenzyl)-1-cyclopropyl-6-iodo-4-oxo-1,4-dihydro-3-quinolinecarboxamide from Preparation No. 20, 0.01 g of copper (I) iodide and 0.04 g of dichlorobis(triphenylphosphine)palladium (II) is added diethylamine (1.5 mL) and propargyl alcohol (0.04 mL). After 3 hours reaction is diluted with DMF (0.5 mL) and left to stir overnight. The reaction is concentrated under reduced pressure, diluted with dichloromethane containing a small amount of methanol, and partioned against water. The organic layer is washed with brine, dried and concentrated under reduced pressure. The residue is adsorbed onto silica and chromatographed on silica eluting with 2% to 6% methanol in dichloromethane . The product-containing fractions are combined and concentrated under reduced pressure to afford 0.17 g of the title compound as a solid.

Workup

  1. customfrom Preparation No
  2. customAfter 3 hours reaction
  3. waitleft
  4. concentrationThe reaction is concentrated under reduced pressure
  5. additiondiluted with dichloromethane containing a small amount of methanol
  6. washThe organic layer is washed with brine
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customchromatographed on silica eluting with 2% to 6% methanol in dichloromethane
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a98a76cdc5734ae78788f9a72845eab0
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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