Potassium Fluoride → [4-(3-Ethynyl-5-trifluoromethyl-benzenesulfonylamino)-4,5,6,7-tetrahydro-indazol-1-yl]-acetic acid ethyl ester

HRID 1645169Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1645169
[CH2:1]([O:3][C:4](=[O:35])[CH2:5][N:6]1[C:14]2[CH2:13][CH2:12][CH2:11][CH:10]([NH:15][S:16]([C:19]3[CH:24]=[C:23]([C:25]#[C:26][Si](C)(C)C)[CH:22]=[C:21]([C:31]([F:34])([F:33])[F:32])[CH:20]=3)(=[O:18])=[O:17])[C:9]=2[CH:8]=[N:7]1)[CH3:2].[F-].[K+]>CN(C)C=O.O>[CH2:1]([O:3][C:4](=[O:35])[CH2:5][N:6]1[C:14]2[CH2:13][CH2:12][CH2:11][CH:10]([NH:15][S:16]([C:19]3[CH:20]=[C:21]([C:31]([F:33])([F:34])[F:32])[CH:22]=[C:23]([C:25]#[CH:26])[CH:24]=3)(=[O:18])=[O:17])[C:9]=2[CH:8]=[N:7]1)[CH3:2]

Komponenten

5

Edukt 2

HCID 522689Potassium FluorideHCID 59152887[4-(3-Trifluoromethyl-5-trimethylsilanylethynyl-benzenesulfonylamino)-4,5,6,7-tetrahydro-indazol-1-yl]-acetic acid ethyl ester

Produkt 1

HCID 59152882[4-(3-Ethynyl-5-trifluoromethyl-benzenesulfonylamino)-4,5,6,7-tetrahydro-indazol-1-yl]-acetic acid ethyl esterAusbeute 98,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of [4-(3-trifluoromethyl-5-trimethylsilanylethynyl-benzenesulfonylamino)-4,5,6,7-tetrahydro-indazol-1-yl]-acetic acid ethyl ester (40.0 mg, 0.076 mmol) in N,N-dimethylformamide and water (3 mL, 150:1) was added potassium fluoride (23.0 mg, 0.30 mmol). The mixture was stirred at room temperature for 4 hours. The resulting mixture was poured into ice and extracted with dichloromethane. The organic layer was washed with brine, dried over sodium sulfate, concentrated and purified by column chromatography (gradient elution, 0-5% methanol in dichloromethane) to afford [4-(3-ethynyl-5-trifluoromethyl-benzenesulfonylamino)-4,5,6,7-tetrahydro-indazol-1-yl]-acetic acid ethyl ester (34.0 mg, 98.2%) as a white solid. MS calcd. for C20H20F3N3O4S 455, obsd. (ESI+) [(M+H)+] 456.

Aufarbeitung

  1. additionThe resulting mixture was poured into ice
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. custompurified by column chromatography (gradient elution, 0-5% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-376e5853dbf64601b9f76dffadc73f80
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08124641B2

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