N,N-Dimethylpropargylamine → HCID 89656225, compound

HRID 626155Notes

Reaction equation

HRID 626155 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1.[CH3:18][N:19]([CH2:21][C:22]#[CH:23])[CH3:20]>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.[Cu]I.CCN(CC)CC>[CH3:18][N:19]([CH3:20])[CH2:21][C:22]#[C:23][C:2]1[N:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 81643N,N-DimethylpropargylamineHCID 11413955Methanone, (6-chloro-3-pyridinyl)(4-methoxyphenyl)-

Product 1

HCID 89656225HCID 89656225, compoundYield 80.2%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

A 25 ml Schlenk flask was charged with (6-chloropyridin-3-yl)(4-methoxy-phenyl)methanone (124 mg, 0.5 mmol), Pd(PPh3)2Cl2 (18 mg, 0.0 25 mmol), CuI (10 mg, 0.05 mmol), Et3N (10 mL), and N,N-dimethylpropargylamine (83 mg, 1.0 mmol). The flask was flushed with argon three times and the mixture was stirred at 80° C. for 24 h. The solvent was evaporated under vacuum and the residue was purified by column chromatography to give the product (118 mg, 80% yield).

Workup

  1. customThe flask was flushed with argon three times
  2. customThe solvent was evaporated under vacuum
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-0aa128dec8d64ad0b3aab15b7d3c244a
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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