Triphenylphosphine → 2-Chloro-5-(2-propenyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

HRID 1765531Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1765531
[Cl:1][C:2]1[CH:21]=[CH:20][C:19](I)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5].[CH2:23]([CH:27]([Sn])C=C(CCCC)CCCC)[CH2:24]CC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl-].[Li+]>[Cl-].[Na+].O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C)C=O>[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:27][CH:23]=[CH2:24])=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5]

Komponenten

8

Edukt 4

HCID 11776TriphenylphosphineHCID 433294Lithium ChlorideHCID 120853472-Chloro-5iodo-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamideHCID 86589045Tributylallyltin

Produkt 1

HCID 211074042-Chloro-5-(2-propenyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamideAusbeute 84,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

2-Chloro-5-iodo-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (prepared as described in WO 99/29661) (7.74 g), tri-n-butylallyltin (5.99 g), dichlorobis(triphenylphosphine)palladium(II) (1.24 g), triphenylphosphine (1.86 g), lithium chloride (6.11 g) and N,N-dimethylformamide. (260 mL) were heated together under nitrogen from 110° C. to 130° C. over 20 minutes, and then at 130° C. for 25 minutes. The mixture was then cooled, poured into brine (500 mL), extracted into ethyl acetate (3×250 mL), dried over anhydrous magnesium sulfate, filtered and concentrated to give an oil. The crude mixture was purified by column chromatography eluting with 9:1 isohexane/ethyl acetate to give the sub-titled compound (5.23 g).

Aufarbeitung

  1. temperature(260 mL) were heated together under nitrogen from 110° C. to 130° C. over 20 minutes
  2. temperatureThe mixture was then cooled
  3. extractionextracted into ethyl acetate (3×250 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an oil
  8. customThe crude mixture was purified by column chromatography
  9. washeluting with 9:1 isohexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-609ee50ed6cd4d9d81fd44b804743d4b
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07227038B2

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