(3-Methoxy-1-propynyl)tributylstannane → 2-(3-Methoxyprop-1-ynyl)-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylester

HRID 1753896Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1753896
[CH3:1][O:2][C:3]([C:5]1[C:6](Cl)=[N:7][C:8]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:9][C:10]=1[CH3:11])=[O:4].C([Sn](CCCC)(CCCC)[C:24]#[C:25][CH2:26][O:27][CH3:28])CCC>O1CCOCC1.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>[CH3:1][O:2][C:3]([C:5]1[C:6]([C:24]#[C:25][CH2:26][O:27][CH3:28])=[N:7][C:8]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:9][C:10]=1[CH3:11])=[O:4]

Komponenten

5

Edukt 2

HCID 10872067(3-Methoxy-1-propynyl)tributylstannaneHCID 866643312-Chloro-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylester

Produkt 1

HCID 866643322-(3-Methoxyprop-1-ynyl)-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylesterAusbeute 63,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 700 mg (2.6 mmol) 2-chloro-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylester and 1.39 g (3.9 mmol) tributyl(3-methoxyprop-1-ynyl)stannane in dioxane (10 ml) was added 273 mg (0.39 mmol) PdCl2(PPh3)2. Then the reaction solution was heated at 100° C. for 16 h. After cooling to RT the mixture was filtered through celite and the filtrate was concentrated in vacuo. The residue was dissolved in EtOAc and washed with water. The organic layer was dried over Na2SO4 and concentrated in vacuo. Purification of the residue by CC (5% KF-silica, hexane/EtOAc 19:1) provided 500 mg (1.64 mmol, 63%) 2-(3-methoxyprop-1-ynyl)-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylester.

Aufarbeitung

  1. temperatureAfter cooling to RT the mixture
  2. filtrationwas filtered through celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with water
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by CC (5% KF-silica, hexane/EtOAc 19:1)

Quellen und Nachweise

ORD-Eintrag
ord-3fd6e8ee9f25422db59d7bad1cd01900
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09168259B2

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