Reaktion #89552

Reaktionsgleichung

6-fluoro-2-iodo-3-methylbenzoic acid

1,2,3-triazole

(1S,2S)—N1,N2-dimethylcyclohexane-1,2-diamine

Cs2CO3

→

title compound

6-Fluoro-3-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas degassed
2. 2
   TemperaturThe reaction was cooled to rt
3. 3
   workup.ADDITIONdiluted with MeOH
4. 4
   SonstigeThe solvent was removed in vacuo
5. 5
   Sonstigeto obtain the crude which
6. 6
   Sonstigewas purified by silica gel chromatography (40% EtOAc in hexanes)

Vorschrift

A mixture of 6-fluoro-2-iodo-3-methylbenzoic acid (900 mg, 3.21 mmol), 1,2,3-triazole (208 μl, 4.82 mmol), (1S,2S)—N1,N2-dimethylcyclohexane-1,2-diamine (103 μl, 642 μmol), Cs2CO3 (1.57 g, 4.82 mmol) and CuI (61 mg, 321 μmol) in DMF (5 mL) was degassed and heated at 120° C. for 1 h in a microwave reactor. The reaction was cooled to rt, diluted with MeOH, and acidified with AcOH to pH 4˜5. The solvent was removed in vacuo to obtain the crude which was purified by silica gel chromatography (40% EtOAc in hexanes) to yield the title compound. MS (ESI) 222 (M+H).

Quelle