Triethylamine → HCID 23658390, Verbindung

HRID 1040314Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1040314
Br[C:2]1[CH:3]=[CH:4][C:5]([C:12]2[CH2:16][C:15]([C:21]3[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=3)([C:17]([F:20])([F:19])[F:18])[O:14][N:13]=2)=[C:6]2[C:11]=1C=NC=C2.[NH2:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1.C([N:39]([CH2:42][CH3:43])[CH2:40][CH3:41])C.[C]=[O:45]>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:28][C:23]1[CH:22]=[C:21]([C:15]2([C:17]([F:20])([F:19])[F:18])[O:14][N:13]=[C:12]([C:5]3[CH:6]=[CH:11][C:2]([C:3]([NH:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=4)=[O:45])=[C:41]4[C:4]=3[CH:43]=[CH:42][N:39]=[CH:40]4)[CH2:16]2)[CH:26]=[C:25]([Cl:27])[CH:24]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 195092-PyridinemethanamineHCID 86645282HCID 86645282, Verbindung2×HCID 178418416HCID 178418416, Verbindung

Produkt 1

HCID 23658390HCID 23658390, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 8-bromo-5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]isoquinoline (i.e. the product from Step C) (20 mg, 0.04 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (PdCl2(dppf)) (6 mg, 0.008 mmol), 2-(aminomethyl)pyridine (17 mg, 0.16 mmol) and triethylamine (0.1 mL, 0.7 mmol) in toluene (2 mL) was purged with carbon monoxide for 15 minutes. Then the reaction vial was maintained with carbon monoxide using a balloon. The reaction mixture was stirred at 70° C. under carbon monoxide atmosphere overnight. The mixture was cooled to room temperature, filtered through a short pad of Celite® diatomaceous filter and rinsed with small amount of ethyl acetate. The filtrate was concentrated and the residue was purified by column chromatography on silica gel using hexanes/ethyl acetate as eluent to provide the title product, a compound of the present invention, as a pale white solid (15 mg).

Aufarbeitung

  1. customwas purged with carbon monoxide for 15 minutes
  2. customThen the reaction
  3. temperatureThe mixture was cooled to room temperature
  4. filtrationfiltered through a short pad of Celite®
  5. filtrationdiatomaceous filter
  6. washrinsed with small amount of ethyl acetate
  7. concentrationThe filtrate was concentrated
  8. customthe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-0c05b53316014aff98dbd08159c756f8
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552218B2

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