Diisopropylethylamine → 6-[2-(Methoxymethyl)pyrrolidin-1-yl]-5-methylnicotinonitrile

HRID 336262Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 336262
[CH3:1][O:2][CH2:3][CH:4]1[CH2:8][CH2:7][CH2:6][NH:5]1.CCN(C(C)C)C(C)C.[C:18]([C:20]1[CH:21]=[C:22]([CH3:27])[C:23](F)=[N:24][CH:25]=1)#[N:19]>C(O)CCC.C(OCC)(=O)C>[CH3:1][O:2][CH2:3][CH:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:23]1[C:22]([CH3:27])=[CH:21][C:20]([C:18]#[N:19])=[CH:25][N:24]=1

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 1439532-(Methoxymethyl)pyrrolidineHCID 232882695-Cyano-2-fluoro-3-picoline

Produkt 1

HCID 675302276-[2-(Methoxymethyl)pyrrolidin-1-yl]-5-methylnicotinonitrileAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2631-ButanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

2-(Methoxymethyl)pyrrolidine (Acb-blocks C5A-0029; 406 mg; 3.53 mmol; 1.2 eq.) and DIEA (1.52 ml; 8.82 mmol; 3 eq.) were added to a solution of 5-cyano-2-fluoro-3-methylpyridine (400 mg; 2.94 mmol; 1 eq.) in 1-butanol (1 mL) and the reaction mixture was stirred at 90° C. for 16 hours. The reaction mixture was allowed to return to room temperature then diluted with ethyl acetate, washed with water, dried over magnesium sulphate and concentrated in vacuo to afford the title compound (0.59 g, 87%) as a yellow oil.

Aufarbeitung

  1. customto return to room temperature
  2. washwashed with water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e86d9e4cc7d94d2387b0284e66532ff1
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889668B2

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