2-(2-Iodo-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester → 2-[3-Methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acid ethyl ester

HRID 1047775Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1047775
[CH2:1]([O:3][C:4]([C:6]1([NH:15][C:16](=[O:25])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=2I)[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:1]([O:3][C:4]([C:6]1([NH:15][C:16](=[O:25])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=2[CH:4]=[C:6]([CH3:14])[CH3:7])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2]

Komponenten

4

Edukt 1

HCID 593141532-(2-Iodo-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester

Produkt 1

HCID 593140782-[3-Methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acid ethyl esterAusbeute 311,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 2-(2-iodo-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (400 mg, 0.89 mmol) and 2,2-dimethyethylenelboronic acid (133 mg, 1.34 mmol) in dioxane (15 mL) is added PdCl2(dppf) ([1,1′-bis(diphenylphosphine)ferrocene]-dichloropalladium(II), 73 mg, 8.9% mmol) and 2M aqueous solution of CsCO3 (1.34 mL, 2.67 mmol). The resulting reaction mixture is covered with argon and run in a microwave reaction: 110° C., 2 h. After concentration in vacuo, the residue is purified by flash column chromatography (120 g silica gel, gradient elution: 5-50% EtOAc in heptane) to give a pure product (134) as a pale yellow solid (523 mg, 78%).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. customrun in a microwave reaction
  3. custom110° C., 2 h
  4. concentrationAfter concentration in vacuo
  5. customthe residue is purified by flash column chromatography (120 g silica gel, gradient elution: 5-50% EtOAc in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-c3682e9c3f7248c5b86311ce8ac7f2c5
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569535B2

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