tert-butyl N-(pent-4-yn-1-yl)carbamate → {5-[2-Amino-5-(3,4-dimethoxy-phenylcarbamoyl)-phenyl]-pent-4-ynyl}-carbamic acid tert-butyl ester

HRID 1039036Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1039036
[C:1]([O:5][C:6](=[O:13])[NH:7][CH2:8][CH2:9][CH2:10][C:11]#[CH:12])([CH3:4])([CH3:3])[CH3:2].[NH2:14][C:15]1[CH:33]=[CH:32][C:18]([C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH3:31])[CH:23]=2)=[O:20])=[CH:17][C:16]=1I>[Cu](I)I.C(NCC)C>[C:1]([O:5][C:6](=[O:13])[NH:7][CH2:8][CH2:9][CH2:10][C:11]#[C:12][C:16]1[CH:17]=[C:18]([C:19](=[O:20])[NH:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH3:31])[CH:23]=2)[CH:32]=[CH:33][C:15]=1[NH2:14])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 22904935tert-butyl N-(pent-4-yn-1-yl)carbamateHCID 672356514-amino-N-(3,4-dimethoxyphenyl)-3-iodobenzamide

Produkt 1

HCID 67235527{5-[2-Amino-5-(3,4-dimethoxy-phenylcarbamoyl)-phenyl]-pent-4-ynyl}-carbamic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 8021DiethylamineLösungsmittel

Versuchsvorschrift

A 500 mL round bottom flask was charged with pent-4-ynyl-carbamic acid tert-butyl ester (1.35 g, 7.37 mmol), 4-amino-N-(3,4-dimethoxyphenyl)-3-iodobenzamide (1.35 g, 6.98 mmol), copper iodide (0.16 g, 0.814 mmol), palladium tetrakistriphenylphosphine (0.81 g, 0.701 mmol), and diethylamine (230 mL) and the resulting mixture stirred at room temperature for 24 h. The resulting mixture was then concentrated in vacuo and the residue purified via flash silica gel chromatography (Analogix IF-280, SF40-400 g column, gradient 90:10-10:90 Heptane:EtOAc) to yield {5-[2-amino-5-(3,4-dimethoxy-phenylcarbamoyl)-phenyl]-pent-4-ynyl}-carbamic acid tert-butyl ester. MS (ES+) 454 (M+1).

Aufarbeitung

  1. concentrationThe resulting mixture was then concentrated in vacuo
  2. customthe residue purified via flash silica gel chromatography (Analogix IF-280

Quellen und Nachweise

ORD-Eintrag
ord-574853d3b9584b8d9538f443a42cb777
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552032B2

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