N-Methoxy-N-methyl-5-phenylethynylnicotinamide → HCID 67047758, Verbindung

HRID 606926Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 606926
[CH3:1][Mg]Br.CON(C)[C:7](=[O:22])[C:8]1[CH:13]=[C:12]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:11]=[N:10][CH:9]=1>C(OCC)C.O1CCCC1.C(OCC)(=O)C>[C:16]1([C:15]#[C:14][C:12]2[CH:13]=[C:8]([C:7](=[O:22])[CH3:1])[CH:9]=[N:10][CH:11]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

6

Edukt 2

HCID 86076555N-Methoxy-N-methyl-5-phenylethynylnicotinamideHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 67047758HCID 67047758, VerbindungAusbeute 85,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Add a 3.0 M solution of methylmagnesium bromide (1.25 mL, 3.8 mmol) in diethyl ether dropwise to a cooled solution of N-methoxy-N-methyl-5-phenylethynyl -nicotinamide, (prepared as described in PREPARATION 2), (1.00 g, 3.7 mmol) in tetrahydrofuran (8.0 mL) at 0° C. Warm to room temperature, stir overnight and dilute with ethyl acetate. Wash with an aqueous saturated solution of ammonium chloride, dry (magnesium chloride), filter and concentrate. Purify the residue by silica gel chromatography, eluting with 10:90 to 30:70 tetrahydrofuran:hexanes, to give the title compound as a white solid (0.70 g, 84%).

Aufarbeitung

  1. washWash with an aqueous saturated solution of ammonium chloride
  2. dry with materialdry (magnesium chloride)
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify the residue by silica gel chromatography
  6. washeluting with 10:90 to 30:70 tetrahydrofuran

Quellen und Nachweise

ORD-Eintrag
ord-d1a93ca48a344f028f3b22e1cfdd130a
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915424B2

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