Reaktion #1798210

Reaktionsgleichung

197

2-Bromo-7-(4-nitrophenoxy)thieno[3,2-b]pyridine

4-methyl-1H-pyrazole

trans-N1,N2-dimethylcyclohexane-1,2-diamine

K2CO3

→

title compound 256

Ausbeute 37.0%

2-(4-Methyl-1H-pyrazol-1-yl)-7-(4-nitrophenoxy)thieno[3,2-b]pyridine

Ausbeute 37.0%

Lösungsmittel

EtOAc

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered through a Celite® pad
2. 2
   Einengenconcentrated under reduced pressure
3. 3
   SonstigeThe residue was purified by flash chromatography with gradient elution with EtOAc/hexane (1:1) to EtOAc/hexane (2:1)

Vorschrift

A mixture of 197 (300 mg, 0.86 mmol, scheme 42), 4-methyl-1H-pyrazole (69 mg, 0.86 mmol), CuI (16.4 mg, 0.086 mmol), trans-N1,N2-dimethylcyclohexane-1,2-diamine (24.4 mg, 0.172 mmol) [J. C. Antilla, A. Klapars, et. al. JACS, 2002, 124, 11684-1688] and K2CO3 (238 mg, 1.72 mmol) in toluene (1.7 mL) was stirred at room temperature in an atmosphere of nitrogen overnight, diluted with EtOAc (100 mL), filtered through a Celite® pad, and concentrated under reduced pressure. The residue was purified by flash chromatography with gradient elution with EtOAc/hexane (1:1) to EtOAc/hexane (2:1) to afford title compound 256 (88.8 mg, 37% yield) as a white solid. MS (m/z): 352.06 (M+1).

Quelle