Isobutanol → Methyl 2-[N-(5-bromo-2-(2-methylpropoxy)benzyl)-N-ethylamino]pyridine-5-carboxylate

HRID 1604371Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1604371
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH2:23][CH2:24][CH3:25])=[C:6]([CH:21]=1)[CH2:7][N:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([O:19][CH3:20])=[O:18])=[CH:13][N:12]=1)[CH2:9][CH3:10].[C:26]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)C(C)C>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH2:23][CH:24]([CH3:26])[CH3:25])=[C:6]([CH:21]=1)[CH2:7][N:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([O:19][CH3:20])=[O:18])=[CH:13][N:12]=1)[CH2:9][CH3:10]

Komponenten

5

Edukt 3

HCID 6560IsobutanolHCID 11776TriphenylphosphineHCID 22622503methyl 2-[N-(5-bromo-2-propoxybenzyl)-N-ethylamino]pyridine-5-carboxylate

Produkt 1

HCID 22622491Methyl 2-[N-(5-bromo-2-(2-methylpropoxy)benzyl)-N-ethylamino]pyridine-5-carboxylateAusbeute 60,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of the methyl-2-[N-(5-bromo-2-(hydroxy-benzyl)-N-ethylamino]pyridine-5-carboxylate (reference example 1, paragraph 7) (0.5 g, 1.37 mmol) in THF (15 ml) was treated with triphenylphosphine (0.39 g, 1.49 mmol) and diazoethyldicarboxylate. The reaction was stirred at ambient temperature for five minutes and then isobutyl alcohol (0.152, 2.06 mmol,) added. The reaction was then stirred at ambient temperature for 18 hours. partitioned between ethyl acetate and water and the aqueous layer washed with ethyl acetate (×2). The organic layers were combined, washed with water and brine, dried (MgSO4) and evaporated. The residue was subjected to chromatography (eluant: ethyl acetate/hexane) to give the title compound (0.35 g, 60%) as an off-white solid.

Aufarbeitung

  1. stirringThe reaction was then stirred at ambient temperature for 18 hours
  2. custompartitioned between ethyl acetate and water
  3. washthe aqueous layer washed with ethyl acetate (×2)
  4. washwashed with water and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-967b209678054b8f9f725e5a74c6c7a3
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05994353

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