Ethyl 4-({6-[(dimethylamino)carbonyl]-1-oxidopyridin-3-yl}oxy)-2-methyl-1-benzofuran-6-carboxylate → Ethyl 4-({6-[(dimethylamino)carbonyl]pyridin-3-yl}oxy)-2-methyl-1-benzofuran-6-carboxylate

HRID 1643747Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1643747
[CH3:1][N:2]([CH3:28])[C:3]([C:5]1[N+:10]([O-])=[CH:9][C:8]([O:12][C:13]2[C:18]3[CH:19]=[C:20]([CH3:22])[O:21][C:17]=3[CH:16]=[C:15]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:14]=2)=[CH:7][CH:6]=1)=[O:4]>C(O)(=O)C.[Fe]>[CH3:28][N:2]([CH3:1])[C:3]([C:5]1[N:10]=[CH:9][C:8]([O:12][C:13]2[C:18]3[CH:19]=[C:20]([CH3:22])[O:21][C:17]=3[CH:16]=[C:15]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:14]=2)=[CH:7][CH:6]=1)=[O:4]

Komponenten

4

Edukt 1

HCID 59560221Ethyl 4-({6-[(dimethylamino)carbonyl]-1-oxidopyridin-3-yl}oxy)-2-methyl-1-benzofuran-6-carboxylate

Produkt 1

HCID 59559976Ethyl 4-({6-[(dimethylamino)carbonyl]pyridin-3-yl}oxy)-2-methyl-1-benzofuran-6-carboxylateAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a stirred solution of ethyl 4-({6-[(dimethylamino)carbonyl]-1-oxidopyridin-3-yl}oxy)-2-methyl-1-benzofuran-6-carboxylate (176 mg, 0.457 mmol) in 15 mL of acetic acid, was added powdered Fe while keeping the temperature at 70° C. for 2 hrs. LC-MS showed that the reaction was complete. The reaction was cooled to room temperature, and the insoluble material was filtered. The mother liquor was diluted with EtOAc, washed with NaHCO3, brine, and dried over Na2SO4, and concentrated. The crude product was introduced into a silica gel column and eluted with MeOH/CHCl3 (2/98 to 5/95) to provide the product (135 mg, 85% yield) as colorless oil. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.40 (t, J=7.16 Hz, 3H) 2.47 (s, 3 H) 3.15 (d, 6 H) 4.39 (q, J=7.03 Hz, 2 H) 6.25 (s, 1 H) 7.30 (d, J=2.45 Hz, 1 H) 7.55-7.64 (m, 1 H) 7.64-7.76 (m, 1 H) 8.00 (s, 1 H) 8.38 (s, 1 H); LC-MS (ESI)+m/z=369.00 (M+H)+.

Aufarbeitung

  1. customat 70° C.
  2. customfor 2 hrs
  3. filtrationthe insoluble material was filtered
  4. additionThe mother liquor was diluted with EtOAc
  5. washwashed with NaHCO3, brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. additionThe crude product was introduced into a silica gel column
  9. washeluted with MeOH/CHCl3 (2/98 to 5/95)

Quellen und Nachweise

ORD-Eintrag
ord-2fc2b37b70194a0cb07bb83eba1a43cc
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08119624B2

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