Propargyl alcohol → HCID 16073829, compound

HRID 1067961Notes

Reaction equation

HRID 1067961 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[C:14]([F:22])[CH:15]=[C:16](I)[CH:17]=3)[N:12]([CH3:23])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1.[CH2:26]([OH:29])[C:27]#[CH:28]>C(NCC)C.C(Cl)Cl.[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:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[C:14]([F:22])[CH:15]=[C:16]([C:28]#[C:27][CH2:26][OH:29])[CH:17]=3)[N:12]([CH3:23])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1

Participants

7

Reactant 2

HCID 7859Propargyl alcoholHCID 21192603HCID 21192603, compound

Product 1

HCID 16073829HCID 16073829, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6344DichloromethaneSolventHCID 8021DiethylamineSolvent

Procedure

A mixture of N-(4-chlorobenzyl)-8-fluoro-6-iodo-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide from Preparation No. 14 (0.600 g), propargyl alcohol (0.11 mL, 1.90 mmol), CuI (0.048 g, 0.25 mmol), and PdCl2(PPh3)2 (0.178 g, 0.25 mmol) in diethylamine (42.5 mL) and CH2Cl2 (50 mL) are warmed to 65° C. overnight. The reaction mixture is then concentratred in vacuo. Column chromatography (elution with 5-10% MeOH/CH2Cl2) gave the title compound as a solid.

Workup

  1. customfrom Preparation No
  2. washColumn chromatography (elution with 5-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-2d3f422dee2946c8b49b40a06ce4f211
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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