Propargyl alcohol → HCID 490484, compound

HRID 1068049Notes

Reaction equation

HRID 1068049 reaction equation
[NH2:1][N:2]1[C:11]2[C:6](=[CH:7][C:8](I)=[CH:9][CH:10]=2)[C:5](=[O:13])[C:4]([C:14]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[O:15])=[CH:3]1.[CH2:25]([OH:28])[C:26]#[CH:27]>C(NCC)C.C(O)C.[Cu]I.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[NH2:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([C:27]#[C:26][CH2:25][OH:28])=[CH:9][CH:10]=2)[C:5](=[O:13])[C:4]([C:14]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[O:15])=[CH:3]1

Participants

7

Reactant 2

HCID 7859Propargyl alcoholHCID 21192582HCID 21192582, compound

Product 1

HCID 490484HCID 490484, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 8021DiethylamineSolvent

Procedure

1-Amino-N-(4-chlorobenzyl)-6-iodo-4-oxo-1,4-dihydro-3-quinolinecarboxamide (0.25 g) from Preparation No. 57, copper (I) iodide (32 mg), and bis(triphenylphosphine)palladium (II) chloride (19 mg) are suspended in diethylamine (8 mL). Propargyl alcohol (39 μL) is added and the mixture is allowed to stir at room temperature for 16 h. The mixture is diluted with ethanol and then concentrated in vacuo. The crude solid is triturated with dichloromethane and recrystallized in acetic acid to affording 76 mg of the title compound as a beige solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude solid is triturated with dichloromethane
  3. customrecrystallized in acetic acid

Sources & evidence

ORD record
ord-d2e24624b39a4e4cbd87d6ec85726602
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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