1h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,2,3-dibromo-1-[(4-fluorophenyl)methyl]-4-hydroxy-,ethyl ester → ethyl 1-(4-fluorobenzyl)-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylate

HRID 2377080Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2377080
Br[C:2]1[N:16]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[C:5]2=[CH:6][N:7]=[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:9]([OH:10])=[C:4]2[C:3]=1Br>C(O)C.[Pd]>[F:24][C:21]1[CH:20]=[CH:19][C:18]([CH2:17][N:16]2[C:5]3=[CH:6][N:7]=[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:9]([OH:10])=[C:4]3[CH:3]=[CH:2]2)=[CH:23][CH:22]=1

Komponenten

4

Edukt 1

HCID 598558191h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,2,3-dibromo-1-[(4-fluorophenyl)methyl]-4-hydroxy-,ethyl ester

Produkt 1

HCID 59855838ethyl 1-(4-fluorobenzyl)-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylateAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A suspension of ethyl 2,3-dibromo-1-(4-fluorobenzyl)-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylate (52.0 g, 0.110 mol) and 10% Pd/C (0.5 g) in ethanol (2.0 L) was shaken in a Parr shaker under hydrogen (39 psi) for 23 h. The catalyst was removed by filtration. On concentration of the filtrate, the product precipitated out. It was collected by filtration and dried under vacuum to provide the title compound. (34 g, 98% yield) 1H NMR (DMSO-d6) δ ppm 11.66 (s, 1H), 8.89 (s, 1H), 8.14 (d, J=3.0 Hz, 1H) 7.37 (d, J=5.7 Hz, 2H), 7.19 (d, J=6.6 Hz, 2H), 7.11 (d, J=3.0 Hz, 1H), 5.71 (s, 2H), 4.45 (q, J=7.1 Hz, 2H), 1.37 (t, J=7.2 Hz, 3H). LC/MS (API-ES, M+H+): 315.1.

Aufarbeitung

  1. customThe catalyst was removed by filtration
  2. customOn concentration of the filtrate, the product precipitated out
  3. filtrationIt was collected by filtration
  4. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-75032037e9664dc794ac249dc424059c
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07468375B2

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