Propargyl alcohol → Tert-butyl 2-[3-[(4-chlorophenyl)methylcarbamoyl]-6-(3-hydroxyprop-1-ynyl)-4-oxo-1-quinolyl]acetate

HRID 1067980Notes

Reaction equation

HRID 1067980 reaction equation
[Cl:1][C:2]1[CH:31]=[CH:30][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]([CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1.C(NCC)C.[CH2:37]([OH:40])[C:38]#[CH:39]>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:31]=[CH:30][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:39]#[C:38][CH2:37][OH:40])[CH:17]=3)[N:12]([CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 7859Propargyl alcoholHCID 8021DiethylamineHCID 21192561tert-butyl 2-[3-{[(4-chlorobenzyl)amino]carbonyl}-6-iodo-4-oxo-1(4H)-quinolinyl]acetate

Product 1

HCID 16073847Tert-butyl 2-[3-[(4-chlorophenyl)methylcarbamoyl]-6-(3-hydroxyprop-1-ynyl)-4-oxo-1-quinolyl]acetate

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 0.23 g of tert-butyl 2-[3-{[(4-chlorobenzyl)amino]carbonyl}-6-iodo-4-oxo-1(4H)-quinolinyl]acetate from Preparation No. 26, 0.01 g of copper (I) iodide and 0.03 g of dichlorobis(triphenylphosphine)palladium (II) is added diethylamine (2.0 mL) and propargyl alcohol (0.03 mL). After 1 hour the reaction is diluted with DMF (1.0 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 4% methanol in dichloromethane . The product-containing fractions are combined and concentrated under reduced pressure to afford 0.13 g of the title compound as a solid.

Workup

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

Sources & evidence

ORD record
ord-7eef102e8804404596248a4a4dd4da5a
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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