Phosphorus oxide (P4O10) → 8-fluoro-3,4-dihydro-2H-benzo[4,5]thieno[3,2-c]pyridin-1-one

HRID 1843962

Reaktionsgleichung

Reaktionsgleichung von HRID 1843962
[F:1][C:2]1[CH:18]=[CH:17][C:5]2[S:6][C:7]([CH2:9][CH2:10][NH:11][C:12](=O)[O:13]CC)=[CH:8][C:4]=2[CH:3]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>O=P(Cl)(Cl)Cl>[F:1][C:2]1[CH:18]=[CH:17][C:5]2[S:6][C:7]3[CH2:9][CH2:10][NH:11][C:12](=[O:13])[C:8]=3[C:4]=2[CH:3]=1

Komponenten

4

Edukt 2

HCID 14812Phosphorus oxide (P4O10)HCID 66803935Ethyl 2-(5-fluorobenzo[b]thiophen-2-yl)ethylcarbamate

Produkt 1

HCID 899641758-fluoro-3,4-dihydro-2H-benzo[4,5]thieno[3,2-c]pyridin-1-oneAusbeute 48,27 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24813Phosphorus oxychlorideLösungsmittel

Versuchsvorschrift

Using analogous conditions and workup as described for the preparation of Intermediate I-1d above, ethyl 2-(5-fluorobenzo[b]thiophen-2-yl)ethylcarbamate (I-50 f: 700 mg, 2.622 mmol) was reacted with P2O5 (749.78 mg, 5.28 mmol) and POCl3 (10 mL) to afford the crude product. Purification by column chromatography on silica gel (50% ethyl acetate in hexane) afforded 280 mg of the product (48.27% yield).

Aufarbeitung

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (50% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-e4f086879660440c883ba8ff2d1de972
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946260B2

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