Sodium Iodide → Methyl 2-{3-bromo-4-[3-(2-methyl-1-pyrrolidinyl)propoxy]phenyl}-4-methyl-1,3-thiazole-5-carboxylate

HRID 1710783Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1710783
[Br:1][C:2]1[CH:3]=[C:4]([C:13]2[S:14][C:15]([C:19]([O:21][CH3:22])=[O:20])=[C:16]([CH3:18])[N:17]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][CH2:11]Cl.[CH3:23][CH:24]1[CH2:28][CH2:27][CH2:26][NH:25]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C.ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([C:13]2[S:14][C:15]([C:19]([O:21][CH3:22])=[O:20])=[C:16]([CH3:18])[N:17]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][CH2:11][N:25]1[CH2:26][CH2:27][CH2:28][CH:24]1[CH3:23]

Komponenten

7

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 130032-MethylpyrrolidineHCID 59457515Methyl 2-[3-bromo-4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylate

Produkt 1

HCID 59457482Methyl 2-{3-bromo-4-[3-(2-methyl-1-pyrrolidinyl)propoxy]phenyl}-4-methyl-1,3-thiazole-5-carboxylateAusbeute 8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A suspension of methyl 2-[3-bromo-4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylate i91 (0.5 g, 1.24 mmol, 1 eq), 2-methylpyrrolidine (0.3 ml, 3.0 mmol, 2.5 eq), potassium carbonate (0.68 g, 5 mmol, 4 eq) and sodium iodide (20 μg, 0.12 mmol, 0.1 eq) in acetonitrile (10 ml) is stirred overnight at 90° C. The resulting mixture is taken up with dichloromethane, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The crude product is triturated in diethyl ether to afford 50 mg of methyl 2-{3-bromo-4-[3-(2-methyl-1-pyrrolidinyl)propoxy]phenyl}-4-methyl-1,3-thiazole-5-carboxylate 126.

Aufarbeitung

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product is triturated in diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-50c528fdb73b498db69f5842650151e0
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790720B2

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