Potassium Carbonate → 4-(4-Amino-3-nitro-phenoxy)-pyridine-2-carboxylic acid dimethylamide

HRID 1915699

Reaktionsgleichung

Reaktionsgleichung von HRID 1915699
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH3:22][N:23]([CH3:33])[C:24]([C:26]1[CH:31]=[C:30](Cl)[CH:29]=[CH:28][N:27]=1)=[O:25].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:22][N:23]([CH3:33])[C:24]([C:26]1[CH:31]=[C:30]([O:8][C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=2)[CH:29]=[CH:28][N:27]=1)=[O:25]

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 3251421Potassium bis(trimethylsilyl)amideHCID 37588824-Amino-3-NitrophenolHCID 49622524-chloro-N,N-dimethylpyridine-2-carboxamide

Produkt 1

HCID 210372944-(4-Amino-3-nitro-phenoxy)-pyridine-2-carboxylic acid dimethylamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture containing 4-amino-3-nitrophenol (1 eq) and potassium bis(trimethylsilyl)amide (2 eq) was stirred in dimethylformamide for 2 hours at room temperature. To this mixture was added 4-Chloro-pyridine-2-carboxylic acid dimethylamide (1 eq) and potassium carbonate (1.2 eq) and then it was stirred at 90° C. for 3 days. The reaction mixture was then concentrated before partitioning between ethyl acetate and water. The organic layer was separated, washed with brine, dried, filtered and concentrated in vacuum to give brown solid. Purification by flash chromatography with ethyl acetate and hexane (1:1) gave the desired product as a yellow syrup. HPLC, 1.69 min; MS: MH+=303.1.

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated
  2. custombefore partitioning between ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with brine
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuum
  8. customto give brown solid
  9. customPurification by flash chromatography with ethyl acetate and hexane (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-65afb5adeb644fc0a6a291ee41cba0c1
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08614330B2

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