Cesium carbonate → 5-(4-(difluoromethoxy)-3-methoxy-2-((3-(methoxymethyl)oxetan-3-yl)methoxy)phenyl)isobenzofuran-1(3H)-one

HRID 2171091Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2171091
Br[C:2]1[C:7]([O:8][CH2:9][C:10]2([CH2:14][O:15][CH3:16])[CH2:13][O:12][CH2:11]2)=[C:6]([O:17][CH3:18])[C:5]([O:19][CH:20]([F:22])[F:21])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C(C)(C)OB([C:37]2[CH:38]=[C:39]3[C:43](=[CH:44][CH:45]=2)[C:42](=[O:46])[O:41][CH2:40]3)O1>CN(C)C=O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:21][CH:20]([F:22])[O:19][C:5]1[CH:4]=[CH:3][C:2]([C:37]2[CH:38]=[C:39]3[C:43](=[CH:44][CH:45]=2)[C:42](=[O:46])[O:41][CH2:40]3)=[C:7]([O:8][CH2:9][C:10]2([CH2:14][O:15][CH3:16])[CH2:13][O:12][CH2:11]2)[C:6]=1[O:17][CH3:18]

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 580746235-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3H-2-benzofuran-1-oneHCID 674676123-((6-Bromo-3-(difluoromethoxy)-2-methoxyphenoxy)methyl)-3-(methoxymethyl)oxetane

Produkt 1

HCID 674668085-(4-(difluoromethoxy)-3-methoxy-2-((3-(methoxymethyl)oxetan-3-yl)methoxy)phenyl)isobenzofuran-1(3H)-oneAusbeute 12 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A stirring solution of 3-((6-bromo-3-(difluoromethoxy)-2-methoxyphenoxy)methyl)-3-(methoxymethyl)oxetane (220 mg, 0.574 mmol) in dimethylformamide (10 mL) was purged with argon for 1 h, to this cesium carbonate (561 mg, 1.72 mmol), tetrakis(triphenylphosphine) palladium(0) (19 mg, 0.017 mmol) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isobenzofuran-1(3H)-one (178 mg, 0.686 mmol) was added and the resultant reaction mixture was heated to 80° C. for 16 h. The reaction mixture was cooled to RT and filtered through celite and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 0-80% ethyl acetate in pet ether) to afford title compound as a solid (30 mg, 12%).

Aufarbeitung

  1. additionwas added
  2. customthe resultant reaction mixture
  3. temperatureThe reaction mixture was cooled to RT
  4. filtrationfiltered through celite
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by column chromatography (silica gel, 0-80% ethyl acetate in pet ether)

Quellen und Nachweise

ORD-Eintrag
ord-aa44654842654b0682a05d720ecf3f37
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09051290B2

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