Cesium carbonate → 6-bromo-1'-[(2R)-tetrahydrofuran-2-ylmethyl]spiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

HRID 2385248Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2385248
[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3([CH2:18][O:19][C:4]=2[CH:3]=1)[C:16]1[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=1)[NH:10][C:9]3=[O:17].C(=O)([O-])[O-].[Cs+].[Cs+].CC1C=CC(S(O[CH2:37][C@H:38]2[CH2:42][CH2:41][CH2:40][O:39]2)(=O)=O)=CC=1>CC(=O)CC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3([CH2:18][O:19][C:4]=2[CH:3]=1)[C:16]1[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=1)[N:10]([CH2:37][C@H:38]1[CH2:42][CH2:41][CH2:40][O:39]1)[C:9]3=[O:17]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 7033050(R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonateHCID 461940506-bromospiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

Produkt 1

HCID 593523336-bromo-1'-[(2R)-tetrahydrofuran-2-ylmethyl]spiro[1-benzofuran-3,3'-indol]-2'(1'H)-oneAusbeute 101,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

To a stirred solution of 6-bromospiro[1-benzofuran-3,3′-indol]-2′(1′H)-one (1.3 g, 4.3 mmol) in 2-butanone (40.0 mL) was added cesium carbonate (4.2 g, 12.9 mmol) and (R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate (1.4 g, 5.4 mmol). The reaction was refluxed for 16 h, filtered and concentrated in vacuo to dryness. The residue was purified by flash chromatography with 25% ethyl acetate in hexanes to afford 6-bromo-1′-[(2R)-tetrahydrofuran-2-ylmethyl]spiro[1-benzofuran-3,3′-indol]-2′(1′H)-one (1.75 g, 100%) as a colorless solid: MS (ES+) m/z 400.0 (M+1), 402.0 (M+1).

Aufarbeitung

  1. temperatureThe reaction was refluxed for 16 h
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo to dryness
  4. customThe residue was purified by flash chromatography with 25% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-cf0b3114a8b5443f80ce562c43cc6f42
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263606B2

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