Trimethylsilylacetylene → Cyclopropyl-ethyl-(2-methyl-4-trimethylsilanylethynyl-benzyl)-amine

HRID 381156Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 381156
Br[C:2]1[CH:14]=[CH:13][C:5]([CH2:6][N:7]([CH:10]2[CH2:12][CH2:11]2)[CH2:8][CH3:9])=[C:4]([CH3:15])[CH:3]=1.[CH3:16][Si:17]([C:20]#[CH:21])([CH3:19])[CH3:18]>C(N(CC)CC)C.[Cu]I.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>[CH:10]1([N:7]([CH2:8][CH3:9])[CH2:6][C:5]2[CH:13]=[CH:14][C:2]([C:21]#[C:20][Si:17]([CH3:19])([CH3:18])[CH3:16])=[CH:3][C:4]=2[CH3:15])[CH2:12][CH2:11]1

Komponenten

6

Edukt 2

HCID 66111TrimethylsilylacetyleneHCID 22568961(4-Bromo-2-methyl-benzyl)-cyclopropyl-ethyl-amine

Produkt 1

HCID 22568965Cyclopropyl-ethyl-(2-methyl-4-trimethylsilanylethynyl-benzyl)-amineAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Using General Procedure D; (4-bromo-2-methyl-benzyl)-cyclopropyl-ethyl-amnine (Intermediate 159, 620.0 mg, 2.31 mmols) in triethylamine (8 mL) was treated with copper(I)iodide (44.0 mg, 0.23 mmol) and then sparged with argon for 15 minutes. Trimethylsilylacetylene (1.04 g, 10.6 mmols) was then added followed by dichlorobis-(triphenylphosphine)palladium(II) (162.0 mg, 0.23 mmol). The resulting reaction mixture was heated to 70° C. for 5 days. The title compound (650.0 mg, 98%) was isolated by chromatography (1-4% EtOAc-hexanes).

Aufarbeitung

  1. customsparged with argon for 15 minutes
  2. customThe resulting reaction mixture

Quellen und Nachweise

ORD-Eintrag
ord-14cebf9688314c4b9e53a885fce85cc8
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06303785B1

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