Piperidine → 1-{2-[4-(4-Bromo-thiophen-2-ylethynyl)-phenoxy]-ethyl}-pyrrolidine

HRID 1916730Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1916730
N1CCCCC1.[Br:7][C:8]1[CH:9]=[C:10]([C:13]#[CH:14])[S:11][CH:12]=1.I[C:16]1[CH:29]=[CH:28][C:19]([O:20][CH2:21][CH2:22][N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:18][CH:17]=1>C1COCC1.[Cu]I>[Br:7][C:8]1[CH:9]=[C:10]([C:13]#[C:14][C:16]2[CH:29]=[CH:28][C:19]([O:20][CH2:21][CH2:22][N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:18][CH:17]=2)[S:11][CH:12]=1

Komponenten

6

Edukt 3

HCID 8082PiperidineHCID 219591661-(2-(4-Iodophenoxy)ethyl)pyrrolidineHCID 534266384-Bromo-2-ethynylthiophene2×

Produkt 1

HCID 673623061-{2-[4-(4-Bromo-thiophen-2-ylethynyl)-phenoxy]-ethyl}-pyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Under an argon atmosphere 0.3 mL (3.13 mmol) piperidine, 14.9 mg (0.08 mmol) CuI and 90.3 mg (0.08 mmol) tetrakis-triphenylphosphane-palladium are added to a solution of 293 mg (1.56 mmol) 4-bromo-2-ethynyl-thiophene and 620 mg (1.56 mmol) 1-[2-(4-iodo-phenoxy)-ethyl]-pyrrolidine in 10 mL THF and the reaction mixture is stirred overnight at RT. To complete the reaction another 150 mg (0.8 mmol) 4-bromo-2-ethynyl-thiophene are added and the mixture is stirred for a further 24 h at RT. The mixture is evaporated down i. vac., the residue is triturated with EtOAc and the insoluble ingredients are filtered off. After the solvent has been eliminated the residue is purified by chromatography (silica gel, EtOAc/MeOH/NH3 8:2:0.2).

Aufarbeitung

  1. additionare added
  2. stirringthe mixture is stirred for a further 24 h at RT
  3. customThe mixture is evaporated down i
  4. custom, the residue is triturated with EtOAc
  5. filtrationthe insoluble ingredients are filtered off
  6. customis purified by chromatography (silica gel, EtOAc/MeOH/NH3 8:2:0.2)

Quellen und Nachweise

ORD-Eintrag
ord-c96fea7864a94beb8b410c4ef128d374
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618132B2

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