Reaktion #166525

Reaktionsgleichung

N-(1-((1H-pyrazol-3-yl)methyl)-3-ethyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

DMF

bromoethane

cesium hydroxide hydrate

→

desired product

Ausbeute 4.8%

N-(3-ethyl-1-((1-ethyl-1H-pyrazol-5-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

Ausbeute 4.8%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered through an Acrodisk
2. 2
   Waschenrinsed with DCM and MeOH
3. 3
   Einengenconcentrated under a nitrogen stream to a residue
4. 4
   WaschenPreparative thin layer chromatography eluting with 10% MeOH, 0.5% NH4OH in CHCl3

Vorschrift

To N-(1-((1H-pyrazol-3-yl)methyl)-3-ethyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (40 mg, 0.10 mmol) in dry DMF (519 μl, 0.10 mmol) was added bromoethane (11 mg, 0.10 mmol), cesium hydroxide hydrate (17 mg, 0.10 mmol) and 4 angstrom molecular sieves. The reaction mixture was stirred for one hour, filtered through an Acrodisk, rinsed with DCM and MeOH, and concentrated under a nitrogen stream to a residue. Preparative thin layer chromatography eluting with 10% MeOH, 0.5% NH4OH in CHCl3 provided the desired product (2 mg). MS (ES+APCI) m/z=414 (M+H). (The other regioisomer, N-(1-((1H-pyrazol-3-yl)methyl)-3-ethyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide, was also isolated and was utilized in Example 40).

Quelle