Propargyl alcohol → HCID 16073857, compound

HRID 1067262Notes

Reaction equation

HRID 1067262 reaction equation
[C:1]([N:5]1[C:14]2[C:9](=[CH:10][C:11](I)=[CH:12][CH:13]=2)[C:8](=[O:16])[C:7]([C:17]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[O:18])=[CH:6]1)([CH3:4])([CH3:3])[CH3:2].[CH2:28]([OH:31])[C:29]#[CH:30]>C(NCC)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>[C:1]([N:5]1[C:14]2[C:9](=[CH:10][C:11]([C:30]#[C:29][CH2:28][OH:31])=[CH:12][CH:13]=2)[C:8](=[O:16])[C:7]([C:17]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[O:18])=[CH:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 7859Propargyl alcoholHCID 21192417HCID 21192417, compound

Product 1

HCID 16073857HCID 16073857, compound

Reagents, catalysts & solvents 3

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

Procedure

To a stirred slurry of 1.15 g of 1-(tert-butyl)-N-(4-chlorobenzyl)-6-iodo-4-oxo-1,4-dihydro-3-quinolinecarboxamide from Preparation No. 10, 156 mg of copper (I) iodide, and 66 mg of dichlorobis(triphenylphosphine)palladium (II) in 23 mL of diethylamine, under argon, is added 0.16 mL of propargyl alcohol. The mixture is stirred for 18 hour at room temperature, then concentrated under reduced pressure. The residue is partitioned between water and chloroform-methanol, and the organic phase dried (MgSO4) and concentrated under reduced pressure. Flash chromatography of the residue on silica using 2-4% methanol in dichloromethane affords 977 mg of tan solid. Recrystallization from ethanol provides 850 mg of the title compound as a beige solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue is partitioned between water and chloroform-methanol
  3. dry with materialthe organic phase dried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-da0514078bbf4c3e9a12cf593bc085db
Source dataset
uspto-grants-2001_06
Patent number
US06248736B1

Reaction notes

Loading…