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4-Bromopyridine → HCID 86594094, Verbindung

HRID 348553
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 348553
Br[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[C:8]1([C@H:14]2[CH2:19][CH2:18][CH2:17][CH2:16][C@H:15]2[N:20]2[CH2:25][CH2:24][CH:23]([NH2:26])[CH2:22][CH2:21]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CC(C)([O-])C.[Na+].Cl.BrC1C=CN=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:8]1([C@H:14]2[CH2:19][CH2:18][CH2:17][CH2:16][C@H:15]2[N:20]2[CH2:25][CH2:24][CH:23]([NH:26][C:2]3[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=3)[CH2:22][CH2:21]2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 4

HCID 142684-BromopyridineHCID 881004-Bromopyridinium chlorideHCID 23676156Sodium t-butoxideHCID 86594093HCID 86594093, Verbindung

Produkt 1

HCID 86594094HCID 86594094, VerbindungAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 167845
palladium(II) acetate
Katalysator
HCID 634876Binap, (A+-)-Katalysator
HCID 1140TolueneLösungsmittel
HCID 3283Diethyl EtherLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

The title compound, MS (ISP): m/e=440.4 (M+H+), was prepared as for example 209, steps (A) to (C). Step (B) was performed using 4-bromo-pyridine as follows: A suspension of (+/−)-[cis-1-(2-phenyl-cyclohexyl)-piperidin-4-yl]-amine (0.303 g, 1.17 mmol) in toluene (10 ml) was degassed with a flow of argon for 10 minutes. Palladium(II) acetate (8.0 mg, 0.036 mmol), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphtyl (BINAP, 23.0 mg, 0.037 mmol), sodium tert-butoxide (0.280 g, 2.91 mmol) and 4-bromopyridine hydrochloride (0.194 g, 1.00 mmol) were added under argon. The flask was sealed and warmed to 70° C. for 3 hours. The mixture was diluted with ethyl acetate (10 ml) and diethyl ether (10 ml) and washed three times with saturated sodium chloride solution. The organic phase was dried with sodium sulphate and evaporated, yielding an orange oil. Purification was achieved by flash chromatography (dichloromethane/methanol/25% NH3 65:10:1). (+/−)-[cis-1-(2-Phenyl-cyclohexyl)-piperidin-4-yl]-pyridin-4-yl-amine (0.187 g, 47%) was obtained as a light yellow foam, MS (ISP): m/e=336.3 (M+H+). This was reacted with benzoyl chloride in step (C).

Aufarbeitung

  1. customwas degassed with a flow of argon for 10 minutes
  2. customThe flask was sealed
  3. washwashed three times with saturated sodium chloride solution
  4. dry with materialThe organic phase was dried with sodium sulphate
  5. customevaporated
  6. customyielding an orange oil
  7. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-348f286791744751807bb7f4761d0fd0
Quelldatensatz
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07176316B2

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