Nitrogen → 3',5'-Dichloro-4'-(2-oxo-3-piperidin-1-yl-pyrrolidin-1-ylmethyl)-biphenyl-4-carboxylic acid methyl ester

HRID 1670843Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1670843
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.[CH3:23][O:24][C:25]([C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1)=[O:26].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>[CH3:23][O:24][C:25]([C:27]1[CH:32]=[CH:31][C:30]([C:2]2[CH:20]=[C:19]([Cl:21])[C:5]([CH2:6][N:7]3[CH2:11][CH2:10][CH:9]([N:12]4[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]4)[C:8]3=[O:18])=[C:4]([Cl:22])[CH:3]=2)=[CH:29][CH:28]=1)=[O:26]

Komponenten

8

Edukt 3

HCID 947NitrogenHCID 27343694-Methoxycarbonylphenylboronic acidHCID 576580161-(4-Bromo-2,6-dichloro-benzyl)-3-piperidin-1-yl-pyrrolidin-2-one

Produkt 1

HCID 576580003',5'-Dichloro-4'-(2-oxo-3-piperidin-1-yl-pyrrolidin-1-ylmethyl)-biphenyl-4-carboxylic acid methyl esterAusbeute 39 %

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 (0.429 g, 1.06 mmol) and 4-methoxycarbonyl phenylboronic acid (0.57 g, 3.16 mmol) in toluene (15 mL) and 2M sodium carbonate (3.7 mL) with N2. Treat the reaction with Pd(PPh3)4 (0.061 g, 0.053 mmol) and heat to 90° C. for 7 hours under N2. Cool the reaction, dilute with ethyl acetate, and wash with water. Dry the organic layer (Na2SO4), remove the solvent in vacuo afford crude product, and purify with a 0 to 10% methanol in CH2Cl2 gradient to afford 0.19 g (39%) of the titled product. Rf=0.40 (9/1 CH2Cl2/methanol). ES MS (m/z): 461 (M+).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-9c6de28b02c245a9ad8e45e0f7fd1b18
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07994176B2

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