Nitrogen → 1-(3,5-Dichloro-4'-fluoro-biphenyl-4-ylmethyl)-3-piperidin-1-yl-pyrrolidin-2-one

HRID 1670842Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1670842
Br[C:2]1[CH:20]=[C:19]([Cl:21])[C:5]([CH2:6][N:7]2[CH2:11][CH2:10][CH:9]([N:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)[C:8]2=[O:18])=[C:4]([Cl:22])[CH:3]=1.[F:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.N#N>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:22][C:4]1[CH:3]=[C:2]([C:27]2[CH:28]=[CH:29][C:24]([F:23])=[CH:25][CH:26]=2)[CH:20]=[C:19]([Cl:21])[C:5]=1[CH2:6][N:7]1[CH2:11][CH2:10][CH:9]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[C:8]1=[O:18]

Komponenten

8

Edukt 3

HCID 947NitrogenHCID 2856454-Fluorophenylboronic acidHCID 576580161-(4-Bromo-2,6-dichloro-benzyl)-3-piperidin-1-yl-pyrrolidin-2-one

Produkt 1

HCID 576579971-(3,5-Dichloro-4'-fluoro-biphenyl-4-ylmethyl)-3-piperidin-1-yl-pyrrolidin-2-oneAusbeute 32,1 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 10340Sodium CarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Purge a mixture of 1-(4-bromo-2,6-dichloro-benzyl)-3-piperidin-1-yl-pyrrolidin-2-one (0.150 g, 0.37 mmol) and 4-fluorophenylboronic acid (0.150 g, 1.07 mmol) in toluene (7 mL) and 2M sodium carbonate (1.3 mL) with N2. Treat the reaction with Pd(PPh3)4 (0.043 g, 0.037 mmol) and heat to 90° C. for 4 hours under N2. Cool the reaction, dilute with ethyl acetate, and wash with and water. Dry the organic layer (Na2SO4), remove the solvent in vacuo to afford crude product, and purify with a 0 to 10% methanol in CH2Cl2 gradient to afford 0.050 g (32%) of the titled product. Rf=0.46 (9/1 CH2Cl2/methanol). ES MS (m/z): 421 (M+).

Aufarbeitung

  1. customPurge
  2. additionTreat
  3. temperatureCool
  4. customthe reaction
  5. washwash with and water
  6. dry with materialDry the organic layer (Na2SO4)
  7. customremove the solvent in vacuo
  8. customto afford crude product
  9. custompurify with a 0 to 10% methanol in CH2Cl2 gradient

Quellen und Nachweise

ORD-Eintrag
ord-b9e46ba1905d42c88ba5925495ea42c4
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07994176B2

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