(Cyclopent-1-en-1-yl)boronic acid → 2-(2-Cyclopent-1-enyl-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester

HRID 1047772Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1047772
[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].[C:26]1(B(O)O)[CH2:30][CH2:29][CH2:28][CH:27]=1>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[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[C:26]2[CH2:30][CH2:29][CH2:28][CH:27]=2)[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2]

Komponenten

5

Edukt 2

HCID 3861343(Cyclopent-1-en-1-yl)boronic acidHCID 593141532-(2-Iodo-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester

Produkt 1

HCID 593141462-(2-Cyclopent-1-enyl-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl esterAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 2-(2-iodo-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (800 mg, 1.78 mmol) and cyclopenten-1-ylboronic acid (796 mg, 7.11 mmol) in dioxane (20 mL) is added Pd(PPh3)4 (412 mg, 0.36 mmol) and 2M aqueous solution of CsCO3 (5.34 mL, 10.7 mmol). The resulting reaction mixture is covered with argon and run in a microwave reaction: 110° C., 2.7 h. After concentration in vacuo, the residue is purified by flash column chromatography (120 g silica gel, gradient elution: 5-40% EtOAc in heptane) to give a pure product (131) as a brown solid (589 mg, 85%).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. customrun in a microwave reaction
  3. custom110° C., 2.7 h
  4. concentrationAfter concentration in vacuo
  5. customthe residue is purified by flash column chromatography (120 g silica gel, gradient elution: 5-40% EtOAc in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-e38c089094be48fd9f1aedf19714b8d0
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569535B2

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