Reaktion #92491

Reaktionsgleichung

3-fluoro-2-iodobenzoic acid

Cs2CO3

2H-1,2,3-triazole

trans-N,N-dimethyl-1,2-cyclohexanediamine

→

3-fluoro-2-(1H-1,2,3-triazol-1-yl)benzoic acid

Lösungsmittel

H2O

dioxane

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to room temperature
2. 2
   Extraktionextracted with EtOAc
3. 3
   Extraktionextracted with EtOAc
4. 4
   SonstigeThe combined organics were dried
5. 5
   Einengenconcentrated
6. 6
   EinengenFrom this concentrate a solid
7. 7
   Sonstigeprecipitated
8. 8
   Sonstigeto provide intermediate A-33 (285 mg, 8%)

Vorschrift

To 3-fluoro-2-iodobenzoic acid (4.5 g, 16.9 mmol) dissolved in dioxane (33.8 mL) and H2O (0.09 mL) was added Cs2CO3 (11.02 g, 33.8 mmol), CuI (161 mg, 0.85 mmol), 2H-1,2,3-triazole (1.96 mL, 33.8 mmol), and trans-N,N-dimethyl-1,2-cyclohexanediamine (0.53 mL, 3.38 mmol). The mixture was then heated to 100° C. overnight, cooled to room temperature, diluted with H2O, and extracted with EtOAc. The aqueous layer was then acidified and extracted with EtOAc. The combined organics were dried and concentrated. From this concentrate a solid precipitated to provide intermediate A-33 (285 mg, 8%). MS (ESI) mass calcd for C9H6FN3O2, 207.0. m/z found 208.1 [M+H]+. 1H NMR (500 MHz, Methanol-d4) δ 6.81-6.77 (m, 1H), 6.46-6.40 (m, 2H), 6.30-6.23 (m, 1H), 6.18-6.12 (m, 1H).

Quelle