tert-butyl N-(prop-2-yn-1-yl)carbamate → tert-Butyl (3-(4-chloro-2-(2,6-difluorobenzoyl)phenyl)prop-2-yn-1-yl)carbamate

HRID 2100397Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2100397
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](I)=[C:6]([C:8]([C:10]2[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=2[F:17])=[O:9])[CH:7]=1.[C:19]([O:23][C:24](=[O:29])[NH:25][CH2:26][C:27]#[CH:28])([CH3:22])([CH3:21])[CH3:20]>C(Cl)Cl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:19]([O:23][C:24](=[O:29])[NH:25][CH2:26][C:27]#[C:28][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][C:6]=1[C:8](=[O:9])[C:10]1[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=1[F:17])([CH3:22])([CH3:21])[CH3:20]

Komponenten

5

Edukt 2

HCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamateHCID 46835488(5-Chloro-2-iodophenyl)(2,6-difluorophenyl)methanone

Produkt 1

HCID 52911151tert-Butyl (3-(4-chloro-2-(2,6-difluorobenzoyl)phenyl)prop-2-yn-1-yl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(5-Chloro-2-iodo-phenyl)-(2,6-difluoro-phenyl)-methanone (2aa) (5.5 g, 14.5 mmol), prop-2-ynyl-carbamic acid tert-butyl ester (2.5 g, 16 mmol), PdCl2(PPh3)2 (0.6 g, 0.9 mmol) and Cu(I)I (0.2 g, 0.9 mmol) were suspended in anhydrous CH2Cl2 (50 mL) and the mixture was sparged with nitrogen for 30 min. Diethylamine (8 mL) was added and the solution was stirred at room temperature for 16 h. The solution was concentrated in vacuo and the resulting residue purified by column chromatography (silica gel, 0 to 15% EtOAc/hexanes) to afford 3aa (3.6 g, 61%) as a white solid, MS m/z=406 (M+H).

Aufarbeitung

  1. customthe mixture was sparged with nitrogen for 30 min
  2. additionDiethylamine (8 mL) was added
  3. concentrationThe solution was concentrated in vacuo
  4. customthe resulting residue purified by column chromatography (silica gel, 0 to 15% EtOAc/hexanes)
  5. customto afford 3aa (3.6 g, 61%) as a white solid, MS m/z=406 (M+H)

Quellen und Nachweise

ORD-Eintrag
ord-1bec7743c27d402180a2b13da1867253
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07572784B2

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