Potassium Carbonate → Methyl 5-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]pyrazine-2-carboxylate

HRID 729451Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 729451
[Br:1][C:2]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.Cl[C:17]1[N:18]=[CH:19][C:20]([C:23]([O:25][CH3:26])=[O:24])=[N:21][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[Br:1][C:2]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:3]=1[O:4][CH:5]1[CH2:6][CH2:7][N:8]([C:17]2[N:18]=[CH:19][C:20]([C:23]([O:25][CH3:26])=[O:24])=[N:21][CH:22]=2)[CH2:9][CH2:10]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 406081Methyl 5-chloropyrazine-2-carboxylateHCID 578327574-(2-Bromo-5-fluorophenoxy)piperidine

Produkt 1

HCID 57832729Methyl 5-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]pyrazine-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 4-(2-bromo-5-fluorophenoxy)piperidine from Step 2 (1.90 g, 6.95 mmol), methyl 5-chloropyrazine-2-carboxylate (1.00 g, 5.79 mmol) and potassium carbonate (1.60 g, 11.59 mmol) in dioxane (30 mL) was heated at 100° C. After a period of 2 h, the reaction mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride. The solvent was separated, dried over sodium sulfate and evaporated. The title compound was purified by flash chromatography (50% ethyl acetate in hexane) to provide the title compound.

Aufarbeitung

  1. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride
  2. customThe solvent was separated
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe title compound was purified by flash chromatography (50% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-62fbe6e62f1a452e8b80e3f3572ea715
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582633B2

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