m-Fluorobenzenethiol → 3'-Fluoro-7-[(3-fluorophenyl)sulfonyl]-2',3,3',4,5',6'-hexahydro-2H-spiro[1-benzofuro[2,3-c]pyridine-1,4'-pyran]

HRID 1616870Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1616870
[F:1][C:2]1[CH:3]=[C:4]([S:8](C2C=CC3C4CCNC5(CCCOC5)C=4OC=3C=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[F:29][CH:30]1[C:35]2([C:40]3[O:41][C:42]4[CH:47]=[C:46](I)[CH:45]=[CH:44][C:43]=4[C:39]=3[CH2:38][CH2:37][NH:36]2)[CH2:34][CH2:33][O:32][CH2:31]1.FC1C=C(S)C=CC=1>>[F:29][CH:30]1[C:35]2([C:40]3[O:41][C:42]4[CH:47]=[C:46]([S:8]([C:4]5[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=5)(=[O:10])=[O:9])[CH:45]=[CH:44][C:43]=4[C:39]=3[CH2:38][CH2:37][NH:36]2)[CH2:34][CH2:33][O:32][CH2:31]1

Komponenten

4

Edukt 3

HCID 75710m-FluorobenzenethiolHCID 533276117-[(3-fluorophenyl)sulfonyl]-3,4,5',6'-tetrahydro-2H,4'H-spiro[1-benzofuro[2,3-c]pyridine-1,3'-pyran]HCID 673236343'-fluoro-7-iodo-2',3,3',4,5',6'-hexahydro-2H-spiro[1-benzofuro[2,3-c]pyridine-1,4'-pyran]

Produkt 1

HCID 533276123'-Fluoro-7-[(3-fluorophenyl)sulfonyl]-2',3,3',4,5',6'-hexahydro-2H-spiro[1-benzofuro[2,3-c]pyridine-1,4'-pyran]

Versuchsvorschrift

As described for 7-[(3-fluorophenyl)sulfonyl]-3,4,5′,6′-tetrahydro-2H,4′H-spiro[1-benzofuro[2,3-c]pyridine-1,3′-pyran] (Example 22) starting from 3′-fluoro-7-iodo-2′,3,3′,4,5′,6′-hexahydro-2H-spiro[1-benzofuro[2,3-c]pyridine-1,4′-pyran] and 3-fluorobenzenethiol The resulting diasteroisomeric mixture was separated using medium pressure liquid chromatography (140 g amine column) eluting with a gradient of EtOAc in hexanes (from 15% to 70% EtOAc).

Aufarbeitung

  1. customwas separated
  2. washeluting with a gradient of EtOAc in hexanes (from 15% to 70% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-85bb2f94004441fd8fe9c895bc519e25
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765779B2

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