Sodium Carbonate → Benzoic acid N'-[3-biphenyl-3-yl-propionyl]-N'-isopropyl-hydrazide

HRID 1724147Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1724147
Br[C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]([N:12]([CH:22]([CH3:24])[CH3:23])[NH:13][C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:11])[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[Na+].[Na+].[C:31]1(B(O)O)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>COCCOC>[C:2]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][C:10]([N:12]([CH:22]([CH3:24])[CH3:23])[NH:13][C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:11])[CH:3]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 57560133benzoic acid N'-[3-(3-bromo-phenyl)-propionyl]-N'-isopropyl-hydrazide

Produkt 1

HCID 57560135Benzoic acid N'-[3-biphenyl-3-yl-propionyl]-N'-isopropyl-hydrazideAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A solution of benzoic acid N′-[3-(3-bromo-phenyl)-propionyl]-N′-isopropyl-hydrazide (100 mg, 0.26 mmol) in DME (5 ml)/2M Na2CO3 (450 μL, 0.90 mmol) was treated with phenylboronic acid (47 mg, 0.39 mmol) and Pd[PPh3]4 (30 mg, 0.026 mmol) for 18 hours at 90° C. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated. The crude was absorbed on silica and purified on a silica gel column with a 30-50% ethyl acetate/hexanes gradient to afford the product as a solid (69 mg, 70%). LC-MS m/e 387.19 (M+H+)

Aufarbeitung

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was absorbed on silica
  7. custompurified on a silica gel column with a 30-50% ethyl acetate/hexanes gradient

Quellen und Nachweise

ORD-Eintrag
ord-5d35a52891f149ee8cf2d43ec6db9797
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07485752B2

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