tert-Butyl acrylate → tert-butyl (E)-3-(2-oxo-2,3-dihydro-1H-indol-5-yl)acrylate

HRID 18241

Reaktionsgleichung

Reaktionsgleichung von HRID 18241
Br[C:2]1[CH:3]=[C:4]2[CH2:10][C:9](=[O:11])[NH:8][C:5]2=N[CH:7]=1.[C:12]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:15])[CH:13]=[CH2:14].[C:21]1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(C(C)C)CC)(C)C>C(#N)CC.CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[O:11]=[C:9]1[CH2:10][C:4]2[C:5](=[CH:21][CH:7]=[C:2](/[CH:14]=[CH:13]/[C:12]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:3]=2)[NH:8]1

Komponenten

8

Edukt 4

HCID 15458tert-Butyl acrylateHCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 155040625-bromo-1H,2H,3H-pyrrolo(2,3-b)pyridin-2-one

Produkt 1

HCID 66905345tert-butyl (E)-3-(2-oxo-2,3-dihydro-1H-indol-5-yl)acrylateAusbeute 162,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 7854PropionitrileLösungsmittel

Versuchsvorschrift

A solution of 5-bromo-1,3-dihydropyrrolo[2,3-b]pyridin-2-one (2.0 g, 9.49 mmole), tert-butyl acrylate (1.8 g, 14.1 mmole), Pd(OAc)2 (0.32 g, 1.4 mmole), tri-ortho-tolylphosphine (0.57 g, 1.9 mmole), and diisopropylethylamine (4.9 mL, 28.2 mmole) in propionitrile (100 mL) and DMF (10 mL) was heated at reflux overnight. The dark mixture was filtered through Celite®, and the filtrate was concentrated. Flash chromatography on silica (9:1 CHCl3/CH3OH containing 5% NH4OH) gave the title compound (0.80 g, 33%) as a light yellow solid. MS (ES) m/e 261 (M+H)+.

Aufarbeitung

  1. temperatureat reflux overnight
  2. filtrationThe dark mixture was filtered through Celite®
  3. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-dc079d50c56847c69bbdaca74f76ae5d
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741339B2

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