p-Toluenesulphonyl cyanide → 2-Chloro-6-fluoroimidazo[1,2-A]pyridine-3-carbonitrile

HRID 705075Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 705075
[Cl:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([F:10])=[CH:6][N:5]2[C:11]=1I.C([Li])CCC.C1(C)C=CC(S([C:27]#[N:28])(=O)=O)=CC=1>O1CCCC1>[Cl:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([F:10])=[CH:6][N:5]2[C:11]=1[C:27]#[N:28]

Komponenten

5

Edukt 3

HCID 87946p-Toluenesulphonyl cyanideHCID 717433442-Chloro-6-fluoro-3-iodoimidazo[1,2-A]pyridineHCID 178418339Butyllithium

Produkt 1

HCID 717433462-Chloro-6-fluoroimidazo[1,2-A]pyridine-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a cooled −78° C. solution of the title compound from Example 3 Step A (0.30 g, 1.01 mmol) in tetrahydrofuran (5.06 ml) was added a solution of n-butyllithium in hexanes (1.6 M, 0.696 ml, 1.11 mmol). After 5 minutes, p-toluenesulfonyl cyanide (0.238 g, 1.32 mmol) was added, and the resulting mixture was allowed to slowly warm to room temperature overnight. The resulting mixture was concentrated under reduced pressure and purified by flash chromatography on silica gel (10-50% ethyl acetate in hexanes) to afford the title compound: LCMS m/z 195.88 [M+H]+, 197.86 [M+2+H]+; 1H NMR (500 MHz, CDCl3) δ 8.25 (d, J=2.4 Hz, 1H), 7.69 (dd, J=9.6, 4.8 Hz, 1H), 7.46-7.42 (m, 1H).

Aufarbeitung

  1. concentrationThe resulting mixture was concentrated under reduced pressure
  2. custompurified by flash chromatography on silica gel (10-50% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-fce6c14083854af4b7c41a00488cfa21
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09173873B2

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