1-Iodo-4-(2-methyl-1-methylene-propyl)-benzene → (1R,2R)-5'-fluoro-2-(4-iodophenyl)-2-isopropylspiro[cyclopropane-1,3'-indolin]-2'-one

HRID 1805309Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1805309
[N+](=[C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:12])[CH:10]=2)[NH:5][C:4]1=[O:13])=[N-].[I:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([CH:23]([CH3:25])[CH3:24])=[CH2:22])=[CH:17][CH:16]=1>C1C=CC=CC=1.C1COCC1>[F:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[NH:5][C:4](=[O:13])[C@:3]12[CH2:22][C@:21]1([C:18]1[CH:17]=[CH:16][C:15]([I:14])=[CH:20][CH:19]=1)[CH:23]([CH3:25])[CH3:24]

Komponenten

5

Edukt 2

HCID 672301281-Iodo-4-(2-methyl-1-methylene-propyl)-benzeneHCID 178514325HCID 178514325, Verbindung

Produkt 1

HCID 58305290(1R,2R)-5'-fluoro-2-(4-iodophenyl)-2-isopropylspiro[cyclopropane-1,3'-indolin]-2'-oneAusbeute 105,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

The 3-diazo-5-fluoroindolin-2-one (0.177 g, 1 mmol) and Rh(OAc)2 dimer (2.2 mg) were placed into a Schlenk tube under Argon atmosphere, then dissolved in dry benzene (3 mL). The mixture was heated to 80° C. for 10 minutes. The 1-iodo-4-(3-methylbut-1-en-2-yl)benzene (0.544 g) was dissolved in dry THF (2 mL) and added into the mixture in one portion. The mixture was concentrated in vacuo, the residue was purified by flash column chromatography (Petroleum ether: AcOEt=5:1) to give the title compound as white powder (0.446 g, 53%). LC/MS m/e calcd. for C19H17FINO: 421, observed (M+H)+: 422.1.

Aufarbeitung

  1. additionadded into the mixture in one portion
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was purified by flash column chromatography (Petroleum ether: AcOEt=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-5f4d20452a4045bfa07ed6c1773935e0
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354443B2

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