Phenol → ethyl 3-(6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)-4-phenoxybenzoate

HRID 930843

Reaktionsgleichung

Reaktionsgleichung von HRID 930843
F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[C:13]1[C:14]2[CH:23]=[CH:22][N:21](S(C3C=CC(C)=CC=3)(=O)=O)[C:15]=2[C:16](=[O:20])[N:17]([CH3:19])[CH:18]=1.[C:34]1([OH:40])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[CH3:19][N:17]1[CH:18]=[C:13]([C:3]2[CH:4]=[C:5]([CH:11]=[CH:12][C:2]=2[O:40][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:14]2[CH:23]=[CH:22][NH:21][C:15]=2[C:16]1=[O:20]

Komponenten

5

Edukt 3

HCID 996PhenolHCID 10796Cesium carbonateHCID 89657255ethyl 4-fluoro-3-(6-methyl-7-oxo-1-tosyl-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzoate

Produkt 1

HCID 71616415ethyl 3-(6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)-4-phenoxybenzoateAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A mixture of Example 9a (1.43 g, 3.05 mmol), phenol (0.0344 g, 3.66 mmol) and cesium carbonate (0.995, 3.05 mmol), in DMSO (15 mL) was heated at 110° C. for 12 hours. After cooling to room temperature, the reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was extracted with additional ethyl acetate twice. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (silica gel, 30-80% ethyl acetate/hexane) to afford 0.85 g (72%) of the title compound. 1H NMR (500 MHz, DMSO-d6) δ 1.31 (t, J=7.02 Hz, 3H), 3.55 (s, 3H), 4.32 (q, J=7.22 Hz, 2H), 6.23 (t, J=2.29 Hz, 1H), 6.97 (d, J=8.54 Hz, 1H), 7.06 (d, J=8.24 Hz, 2H), 7.17 (t, J=7.32 Hz, 1H), 7.28 (t, J=2.75 Hz, 1H), 7.36-7.51 (m, 3H), 7.94 (dd, J=8.7, 2.29 Hz, 1H), 8.04 (d, J=2.14 Hz, 1H), 12.02 (s, 1H). MS (ESI+) m/z 389.2 (M+H)+.

Aufarbeitung

  1. customthe reaction mixture was partitioned between water and ethyl acetate
  2. extractionThe aqueous layer was extracted with additional ethyl acetate twice
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (silica gel, 30-80% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-b715ee3307b2443cab72685d8f09f67b
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296741B2

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