Triethylamine → 3,3-Dimethyl-1-[2-(6-(3-pyridyl)hex-5 ynoyl)perhydropyridazinyl] pentane-1,2-dione

HRID 2228459

Reaction equation

HRID 2228459 reaction equation
[C:1]([N:8]1[CH:13]([C:14](=[O:22])[C:15](=[O:21])[C:16]([CH3:20])([CH3:19])[CH2:17][CH3:18])[CH2:12][CH2:11][CH2:10][NH:9]1)(=[O:7])[CH2:2][CH2:3][CH2:4][C:5]#[CH:6].I[C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1.C(N(CC)CC)C>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>[CH3:20][C:16]([CH3:19])([CH2:17][CH3:18])[C:15](=[O:21])[C:14]([CH:13]1[CH2:12][CH2:11][CH2:10][NH:9][N:8]1[C:1](=[O:7])[CH2:2][CH2:3][CH2:4][C:5]#[C:6][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)=[O:22]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 707143-IodopyridineHCID 184700651-(2-Hex-5-ynoylperhydropyridazinyl)-3,3-dimethylpentane-1,2-dione

Product 1

HCID 184700723,3-Dimethyl-1-[2-(6-(3-pyridyl)hex-5 ynoyl)perhydropyridazinyl] pentane-1,2-dioneYield 65%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

To a solution of 1-(2-hex-5-ynoylperhydropyridazinyl)-3,3-dimethylpentane-1,2-dione (0.384 g, 1.25 mmol) in 10 ml CH2Cl2under nitrogen was added 3-iodopyridine (0.283 g, 1.38 mmol), (Ph3P)2PdCl2 (0.044 g, 0.06 mmol), CuI (0.0024 g, 0.013 mmol) and triethylamine (0.3 ml, 2 mmol). The reaction mixture was stirred 30 minutes at room temperature and then refluxed overnight. The mixture was concentrated and purified by silica gel column, eluting with 30% ethyl acetate in hexane, to yield product as light yellow oil (0.31 g, 65%). 1H NMR (CDCl3, 400 MHz) δ 0.84 (t, 3H, J=7.4); 1.21 (s, 6H); 1.70 (m, 6H); 1.96(m, 2H), 2.52 (m, 3H); 2.90 (m, 2H); 3.60 (m, 1H); 4.42 (m, 2H); 7.20 (m, 1H); 7.66 (m, H); 8.49 (m, 1H); 8.62 (m, 1H).

Workup

  1. temperaturerefluxed overnight
  2. concentrationThe mixture was concentrated
  3. custompurified by silica gel column
  4. washeluting with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-a2f5d4ad34594efb9a9f46e13d55d5b0
Source dataset
uspto-grants-2002_07
Patent number
US06417189B1

Linked notes

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