Potassium Carbonate → 4-(2-Fluoro-4-nitrophenoxy)-2-methyl-1H-pyrrolo[2,3-b]pyridine

HRID 2117166Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2117166
[CH3:1][C:2]1[NH:11][C:5]2[N:6]=[CH:7][CH:8]=[C:9]([OH:10])[C:4]=2[CH:3]=1.[F:12][C:13]1[CH:14]=[C:15]([N+:20]([O-:22])=[O:21])[CH:16]=[CH:17][C:18]=1F.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[F:12][C:13]1[CH:14]=[C:15]([N+:20]([O-:22])=[O:21])[CH:16]=[CH:17][C:18]=1[O:10][C:9]1[CH:8]=[CH:7][N:6]=[C:5]2[NH:11][C:2]([CH3:1])=[CH:3][C:4]=12

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 178422234HCID 178422234, Verbindung

Produkt 1

HCID 210816374-(2-Fluoro-4-nitrophenoxy)-2-methyl-1H-pyrrolo[2,3-b]pyridineAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of 2-methyl-1H-pyrrolo[2,3-b]pyridin-4-ol (90 mg, TFA salt, 0.34 mmol), 3,4-difluoronitrobenzene (0.05 mL) and potassium carbonate (100 mg, 0.72 mmol) in DMF (1 mL) was stirred at 50° C. for 2 h. The mixture was diluted with water and extracted with ethyl acetate (3×5 mL). The combined extracts were washed with water, dried (MgSO4) and concentrated in vacuo to afford the crude product, which was purified by preparative HPLC to give the title compound (45 mg, 46%). 1H NMR (CD3OD) δ 8.25 (dd, 2H, J=10.4, 2.6 Hz), 8.12 (m, 1H), 8.04 (d, 1H, J=5.5 Hz), 7.30 (t, 1H, J=8.3 Hz), 6.67 (d, 1H, J=5.5 Hz), 5.95 (s, 1H), 2.41 (s, 3H); MS(ESI+) m/z 288 (M+H)+.

Aufarbeitung

  1. extractionextracted with ethyl acetate (3×5 mL)
  2. washThe combined extracts were washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto afford the crude product, which
  6. customwas purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-251d103fdcd14913a8fff803fe5553b3
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07439246B2

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