Cesium carbonate → 3-(2-Fluoro-4-methylsulfanyl-phenylamino)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester

HRID 2264943Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2264943
[CH2:1]([O:3][C:4]([C:6]1[NH:14][C:13]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1[NH2:15])=[O:5])[CH3:2].Br[C:17]1[CH:22]=[CH:21][C:20]([S:23][CH3:24])=[CH:19][C:18]=1[F:25].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:1]([O:3][C:4]([C:6]1[NH:14][C:13]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1[NH:15][C:17]1[CH:22]=[CH:21][C:20]([S:23][CH3:24])=[CH:19][C:18]=1[F:25])=[O:5])[CH3:2]

Komponenten

8

Edukt 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23218185ethyl 3-amino-1H-pyrrolo[3,2-c]pyridine-2-carboxylateHCID 253072224-Bromo-3-fluorothioanisole

Produkt 1

HCID 595966043-(2-Fluoro-4-methylsulfanyl-phenylamino)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl esterAusbeute 24,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A degassed solution of 3-amino-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester (0.610 g, 3 mmol), 1-bromo-2-fluoro-4-methylsulfanyl-benzene (1.13 g, 5.1 mmol), Pd2dba3 (0.14 g, 0.15 mmol), Xantphos (0.17 g, 0.3 mmol) and cesium carbonate (1.94 g, 6.0 mmol) in toluene (20 ml) was subjected to microwave irradiation at 150° C. for 2 hours. The reaction mixture was cooled to ambient temperature then diluted with ethyl acetate and filtered through a pad of Celite®. The filtrate was concentrated under reduced pressure to give a residue that was purified by flash chromatography (Si-PPC, ethyl acetate: DCM, gradient 0:100 to 40:100) to afford the title compound as a yellow solid (0.25 g, 24%). LCMS (method B): RT=2.45 min, M+H+=346.

Aufarbeitung

  1. customirradiation at 150° C. for 2 hours
  2. filtrationfiltered through a pad of Celite®
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customto give a residue that
  5. customwas purified by flash chromatography (Si-PPC, ethyl acetate: DCM, gradient 0:100 to 40:100)

Quellen und Nachweise

ORD-Eintrag
ord-3922522de1be410aaed2fe1ce79546e3
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07855216B2

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