Iodoethane → HCID 117992935, Verbindung

HRID 922580Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 922580
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[C:4]([F:11])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:18](I)[CH3:19]>CS(C)=O>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH2:18][CH3:19])=[C:4]([F:11])[CH:3]=1.[Br:1][C:2]1[CH:3]=[C:4]([F:11])[C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([CH2:18][CH3:19])[CH:6]=2

Komponenten

6

Edukt 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 247287446-Bromo-4-fluoro-1H-indazole

Produkt 2

HCID 117992935HCID 117992935, VerbindungAusbeute 52 %HCID 117992991HCID 117992991, VerbindungAusbeute 17 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a solution of 6-bromo-4-fluoro-1H-indazole (1000 g, 4.65 mol) in DMSO (5.0 L), was added K2CO3 (900 g, 6.51 mol), followed by addition of ethyl iodide (900 g, 5.77 mol). The reaction mixture was stirred at r.t. for 16 h. The reaction mixture was poured into ice water and extracted with EtOAc. The organic layer was dried and concentrated. The residue was purified by silica gel column chromatography (0-10% EtOAc in hexanes) to give 6-bromo-1-ethyl-4-fluoro-1H-indazole (595 g, 2.45 mol, 52%) as a yellow oil and 6-bromo-2-ethyl-4-fluoro-2H-indazole (278 g, 1.14 mol, yield 17%) as an orange solid. 1H NMR (600 MHz, CDCl3) δ 1.52 (t, 3H), 4.39 (q, 2H), 6.95 (dd, 1H), 7.40 (s, 1H), 8.02 (s, 1H). MS (ES+)(M+H) 243.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (0-10% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-076eb262a5ab47c4996e9acdc0648546
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278953B2

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