Propargyl alcohol → HCID 10318611, compound

HRID 1068019Notes

Reaction equation

HRID 1068019 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][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]([CH3:22])[CH:11]=2)=[S:9])=[CH:4][CH:3]=1.[CH2:25]([OH:28])[C:26]#[CH:27]>C(NCC)C.[Cu](I)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>[Cl:1][C:2]1[CH:24]=[CH:23][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:27]#[C:26][CH2:25][OH:28])[CH:17]=3)[N:12]([CH3:22])[CH:11]=2)=[S:9])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 7859Propargyl alcoholHCID 21192539HCID 21192539, compound

Product 1

HCID 10318611HCID 10318611, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8021DiethylamineSolvent

Procedure

A suspension of N-(4-chlorobenzyl)-6-iodo-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarbothioamide (0.20 g) from Preparation No. 44, propargyl alcohol (0.030 mL), copper iodide (0.028 g), and bis(triphenylphosphine)palladium(II)chloride (0.0095 g) in diethylamine (10 mL) is stirred at room temperature for 18 h. The solid in the reaction mixture is filtered, then dissolved in CH2Cl2/MeOH, and adsorbed onto silica. Purification by chromatography (eluent 1% MeOH:CH2Cl2 (1 L), 2% MeOH:CH2Cl2 (1 L)) affords the title compound as a yellow solid (0.12 g).

Workup

  1. customfrom Preparation No
  2. filtrationThe solid in the reaction mixture is filtered
  3. dissolutiondissolved in CH2Cl2/MeOH
  4. customPurification by chromatography (eluent 1% MeOH:CH2Cl2 (1 L), 2% MeOH:CH2Cl2 (1 L))

Sources & evidence

ORD record
ord-7733e59cd787423fbfd7163097390032
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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