Potassium Carbonate → 4-[3-Difluoromethoxy-2-hydroxy-6-(1-oxo-1,3-dihydro-isobenzofuran-5-yl)-phenoxymethyl]-benzenesulfonamide

HRID 2171087Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2171087
[F:1][CH:2]([F:23])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[C:15](=[O:19])[O:14][CH2:13]3)=[C:6]([OH:20])[C:5]=1[O:21]C.C(=O)([O-])[O-].[K+].[K+].Br[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([S:38]([NH2:41])(=[O:40])=[O:39])=[CH:34][CH:33]=1>C(#N)C>[F:23][CH:2]([F:1])[O:3][C:4]1[C:5]([OH:21])=[C:6]([C:7]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[C:15](=[O:19])[O:14][CH2:13]3)=[CH:8][CH:9]=1)[O:20][CH2:31][C:32]1[CH:33]=[CH:34][C:35]([S:38]([NH2:41])(=[O:40])=[O:39])=[CH:36][CH:37]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 131545004-BromomethylbenzenesulfonamideHCID 674684075-(4-(difluoromethoxy)-2-hydroxy-3-methoxyphenyl)isobenzofuran-1(3H)-one

Produkt 1

HCID 545778144-[3-Difluoromethoxy-2-hydroxy-6-(1-oxo-1,3-dihydro-isobenzofuran-5-yl)-phenoxymethyl]-benzenesulfonamideAusbeute 47,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirring solution of 5-(4-(difluoromethoxy)-2-hydroxy-3-methoxyphenyl)isobenzofuran-1(3H)-one (100 mg, 0.310 mmol) in acetonitrile (20 mL), was added potassium carbonate (128.3 mg, 0.930 mmol) and 4-bromomethyl-benzenesulfonamide (155.2 mg, 0.620 mmol) and the resultant reaction mixture was heated to 80° C. for 16 h. The reaction mixture was cooled to RT, filtered through celite and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 0-70% ethyl acetate in pet ether) to afford title compound as a solid (70 mg, 46%).

Aufarbeitung

  1. customthe resultant reaction mixture
  2. temperatureThe reaction mixture was cooled to RT
  3. filtrationfiltered through celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by column chromatography (silica gel, 0-70% ethyl acetate in pet ether)

Quellen und Nachweise

ORD-Eintrag
ord-647b2219449340109ef0d79416ca922d
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09051290B2

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