Chlorosuccinimide → 2-(5-(3-Chloro-6-fluoroimidazo[1,2-a]pyridin-2-yl)pyridin-3-yl)propan-2-ol

HRID 705071Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 705071
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:12]=[C:13]([C:17]([OH:20])([CH3:19])[CH3:18])[CH:14]=[N:15][CH:16]=3)[N:10]=2)[CH:7]=1.[Cl:21]N1C(=O)CCC1=O>C(#N)C>[Cl:21][C:8]1[N:6]2[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]2=[N:10][C:9]=1[C:11]1[CH:12]=[C:13]([C:17]([OH:20])([CH3:18])[CH3:19])[CH:14]=[N:15][CH:16]=1

Komponenten

4

Edukt 2

HCID 31398ChlorosuccinimideHCID 867303792-(5-(6-Fluoroimidazo[1,2-a]pyridin-2-yl)pyridin-3-yl)propan-2-ol

Produkt 1

HCID 867303802-(5-(3-Chloro-6-fluoroimidazo[1,2-a]pyridin-2-yl)pyridin-3-yl)propan-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of the title compound from Example 2 Step E (0.068 g, 0.251 mmol) in acetonitrile (1.25 ml) was added N-chlorosuccinimide (0.040 g, 0.301 mmol). The resulting mixture was stirred at room temperature for 2 hours, then concentrated under reduced pressure. The resulting residue was diluted with dichloromethane, washed with saturated aqueous sodium chloride solution, dried over MgSO4, filtered, and concentrated under reduced pressure. Purification by flash chromatography on silica gel (100% ethyl acetate) provided the title compound: LCMS m/z 306.08 [M+H]+; 1H NMR (500 MHz, CDCl3) 9.23 (d, J=1.7 Hz, 1H), 8.78 (d, J=2.1 Hz, 1H), 8.51 (t, J=2.0 Hz, 1H), 8.08 (t, J=2.5 Hz, 1H), 7.65 (dd, J=9.3, 4.9 Hz, 1H), 7.24-7.20 (m, 1H), 2.02 (br s, 1H), 1.69 (s, 6H).

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. additionThe resulting residue was diluted with dichloromethane
  3. washwashed with saturated aqueous sodium chloride solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash chromatography on silica gel (100% ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-295967e22f0241fa8a025bc34b2b7e5d
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09173873B2

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