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

HRID 219811Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 219811
[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.CCOC(C)=O>[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 (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 RT then diluted with EtOAc, washed with water, dried over MgSO4 and concentrated in vacuo to afford the title compound as a yellow oil (0.59 g, 87%). LC/MS (Method A): 200.1 (M+H)+. HPLC (Method A) Rt 2.42 min (Purity 99.1%).

Aufarbeitung

  1. customto return to RT
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-eac71cda286a4d9283d2ad9e0699d44f
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202865B2

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