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Water → 4-[4-(1-fluoro-1-methyl-2-{[(methylethyl)sulfonyl]amino}ethyl)phenyl]benzoic Acid

HRID 1797177
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1797177
[F:1][C:2]([C:12]1[CH:17]=[CH:16][C:15](I)=[CH:14][CH:13]=1)([CH3:11])[CH2:3][NH:4][S:5]([CH:8]([CH3:10])[CH3:9])(=[O:7])=[O:6].[C:19]([C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)([OH:21])=[O:20].C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1.O>[F:1][C:2]([C:12]1[CH:17]=[CH:16][C:15]([C:25]2[CH:26]=[CH:27][C:22]([C:19]([OH:21])=[O:20])=[CH:23][CH:24]=2)=[CH:14][CH:13]=1)([CH3:11])[CH2:3][NH:4][S:5]([CH:8]([CH3:10])[CH3:9])(=[O:7])=[O:6]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 3121834-Carboxyphenylboronic AcidHCID 9800265[2-Fluoro-2-(4-iodophenyl)propyl][(methylethyl)sulfonyl]amine

Produkt 1

HCID 221765834-[4-(1-fluoro-1-methyl-2-{[(methylethyl)sulfonyl]amino}ethyl)phenyl]benzoic AcidAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 218864351,4-Dioxane--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Scheme VI, Step A′: Into a 50 mL single neck flask [2-fluoro-2-(4-iodophenyl)propyl][(methylethyl)sulfonyl]amine (300 mg, 0.78 mmol, prepared in example 1), 4-carboxybenzene boronic acid (188 mg, 1.13 mmol), potassium carbonate (156 mg, 1.13 mmol) and tetrakis(triphenyl phosphine)palladium(0) (52 mg, 0.05 mmol) were combined in dioxane/water (30 mL, 3:1). The mixture was then heated at 100° C. with stirring for 18 hours. The reaction was cooled to room temperature and poured into H2O. The desired product was extracted with ethyl acetate and the organic layer was separated, washed twice with H2O, dried over K2CO3, and concentrated under reduced vacuum to yield the crude material (350 mg) as a tan solid. The crude material was purified via silica gel chromatography employing the Chromatotron using a 4000 micron rotor and eluting with a solvent of methylene chloride/methanol 9:1 to yield the title compound (91 mg, 31%) as a white solid.

Aufarbeitung

  1. temperatureThe reaction was cooled to room temperature
  2. extractionThe desired product was extracted with ethyl acetate
  3. customthe organic layer was separated
  4. washwashed twice with H2O
  5. dry with materialdried over K2CO3
  6. concentrationconcentrated under reduced vacuum
  7. customto yield the crude material (350 mg) as a tan solid
  8. customThe crude material was purified via silica gel chromatography
  9. washeluting with a solvent of methylene chloride/methanol 9:1

Quellen und Nachweise

ORD-Eintrag
ord-2b39fd69abca49158e8a8586426b32f2
Quelldatensatz
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07034045B1

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