Methanesulfonic Acid → 6-Chloro-3-iodo-1-tetrahydropyran-2-yl-pyrazolo[4,3-c]pyridine

HRID 1778797Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1778797
[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8]([I:11])=[N:9][NH:10][C:4]=2[CH:3]=1.CS(O)(=O)=O.[O:17]1[CH:22]=[CH:21][CH2:20][CH2:19][CH2:18]1>C(Cl)Cl.O1CCCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8]([I:11])=[N:9][N:10]([CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22][O:17]3)[C:4]=2[CH:3]=1

Komponenten

6

Edukt 3

HCID 6395Methanesulfonic AcidHCID 80803,4-dihydro-2H-pyranHCID 1784778336-chloro-3-iodo-1H-pyrazolo[4,3-c]pyridine

Produkt 1

HCID 867228756-Chloro-3-iodo-1-tetrahydropyran-2-yl-pyrazolo[4,3-c]pyridineAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

At r.t. to a suspension of 6-chloro-3-iodo-1H-pyrazolo[4,3-c]pyridine (0.55 g, 2.0 mmol) in methylene chloride (6 mL) and tetrahydrofuran (3 mL) was added methanesulfonic acid (20 μL, 0.4 mmol), followed by dihydropyran (0.54 mL, 5.9 mmol) (Aldrich, Cat. #: D106208). The mixture was stirred at r.t. overnight. Then, it was stirred at 60° C. for 4 h. After cooling it was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%) to afford the desired product (0.72 g).

Aufarbeitung

  1. stirringThen, it was stirred at 60° C. for 4 h
  2. temperatureAfter cooling it
  3. concentrationwas concentrated under reduced pressure
  4. customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%)

Quellen und Nachweise

ORD-Eintrag
ord-8c2ccc21f20845d6803919f0689c74dd
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09266892B2

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