2-Fluoro-4-nitrophenol → Methyl 7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine-2-carboxylate

HRID 500763Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 500763
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[S:10][C:3]=12.[F:15][C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]=1[OH:25].C([O-])([O-])=O.[K+].[K+]>O(C1C=CC=CC=1)C1C=CC=CC=1.CCOC(C)=O>[F:15][C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]=1[O:25][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[S:10][C:3]=12

Komponenten

6

Edukt 3

HCID 98252-Fluoro-4-nitrophenolHCID 11430Potassium CarbonateHCID 59424429Methyl 7-chlorothieno[3,2-B]pyridine-2-carboxylate

Produkt 1

HCID 59424450Methyl 7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine-2-carboxylateAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7583Diphenyl EtherLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

A mixture of 37 (4.0 g, 17.6 mmol), 2-fluoro-4-nitrophenol (5.5 g, 35.0 mmol) and K2CO3 (12.1 g, 87.5 mmol) in Ph2O was heated at 180° C. for 5 hours. The mixture was cooled to room temperature, diluted with EtOAc and washed with water. The organic phase was collected, dried over anhydrous sodium sulfate and the solvents were removed under reduced pressure. The residue was purified by flash chromatography using hexane—AcOEt (70:30) as an eluent. The product from the column was re-crystallized from a mixture of ethyl acetate-hexanes to afford 38 (3.6 g, 59% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.69 (d, J=5.2 Hz, 1H), 8.47 (dd, J=2.4 and 10.0 Hz, 1H), 8.27 (s, 1H), 7.77 (dd, J=8.0 and 9.2 Hz, 1H), 7.06 (dd, J=0.8 and 5.2 Hz, 1H), 3.93 (s, 3H).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed with water
  3. customThe organic phase was collected
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvents were removed under reduced pressure
  6. customThe residue was purified by flash chromatography
  7. customThe product from the column was re-crystallized from a mixture of ethyl acetate-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-24d4670dd2874471ab5ae527c5809161
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772247B2

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