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Methyl 6-formylpyridine-3-carboxylate → HCID 67980582, Verbindung

HRID 2406949
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2406949
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:4]=1)=O.[F:13][C:14]([F:29])([F:28])[C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=2)=[CH:17][CH:16]=1.[CH2:30]([Mg]Br)[CH:31]([CH3:33])[CH3:32]>O1CCCC1.[Cl-].[Zn+2].[Cl-]>[CH3:30][CH:31]([CH3:33])[CH2:32][CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:4]=1)[NH:27][C:24]1[CH:25]=[CH:26][C:21]([C:18]2[CH:19]=[CH:20][C:15]([C:14]([F:28])([F:29])[F:13])=[CH:16][CH:17]=2)=[CH:22][CH:23]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 586269Methyl 6-formylpyridine-3-carboxylateHCID 27827094'-(Trifluoromethyl)[1,1'-biphenyl]-4-amineHCID 178418816HCID 178418816, Verbindung

Produkt 1

HCID 67980582HCID 67980582, VerbindungAusbeute 39,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysator
HCID 8028
Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of methyl 6-formylnicotinate (0.200 g, 1.21 mmol) in tetrahydrofuran (8 mL) containing activated molecular sieves was added 4′-(trifluoromethyl)biphenyl-4-amine (316 mg, 1.33 mmol). The reaction was heated to 90° C. and stirred overnight. The reaction was concentrated to dryness and the residue was dissolved in tetrahydrofuran (8 mL). The solution was cooled to 0° C. Zinc chloride (3.52 mL, 1M in diethyl ether, 3.52 mmol) was added, followed by isobutylmagnesium bromide (1.47 mL, 2.0M in THF, 3.52 mmol). The reaction was stirred at 0° C. for 2 hours. The reaction was quenched with saturated ammonium chloride. The mixture was diluted with dichloromethane and water. The layers were separated and the aqueous was extracted again with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered and concentrated. Purification by column chromatography gave methyl 6-(3-methyl-1-(4′-(trifluoromethyl)biphenyl-4-ylamino)butyl)nicotinate (210 mg, 39%) as a yellow oil. 1H NMR (400 MHz, CD3OD, δ): 9.09 (s, 1H), 8.31 (d, 1H), 7.72-7.57 (m, 5H), 7.41 (d, 2H), 6.65 (d, 2H), 4.61-4.52 (m, 1H), 3.94 (s, 3H), 1.92-1.73 (m, 2H), 1.1.72-1.61 (m, 1H), 1.05 (d, 3H), 0.91 (d, 3H).

Aufarbeitung

  1. concentrationThe reaction was concentrated to dryness
  2. dissolutionthe residue was dissolved in tetrahydrofuran (8 mL)
  3. temperatureThe solution was cooled to 0° C
  4. stirringThe reaction was stirred at 0° C. for 2 hours
  5. customThe reaction was quenched with saturated ammonium chloride
  6. additionThe mixture was diluted with dichloromethane and water
  7. customThe layers were separated
  8. extractionthe aqueous was extracted again with dichloromethane
  9. dry with materialThe combined organic layers were dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customPurification by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b1f06747736541a5b962b6c9e63ad8db
Quelldatensatz
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08809342B2

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