反应详情

Trimethylaluminum (0.11 mL of a 2 N solution in hexane, 0.22 mmol) was added to a stirred solution of 3-(trifluoromethoxy)benzyl amine (42 mg, 0.22 mmol) in anhydrous chloroform (2 mL) under nitrogen and the resulting solution was stirred at room temperature for 20 minutes. Ethyl 5-(3,5-dibromo-4-hydroxyphenyl)-1,2,4-oxadiazole-3-carboxylate (78 mg, 0.2 mmol) was then added in one portion and the reaction was stirred at 50° C. for 5 h before standing at room temperature overnight. Water (2 mL) was added followed by more chloroform (3 mL), the organic phase was separated and evaporated to dryness to give a yellow oil. This was purified by preparative HPLC to give the title compound (66 mg, 62%) as a colourless solid. 1H NMR δ (ppm) (DMSO-d6): 4.58 (2 H, d, J=6.20 Hz), 7.31 (1 H, d, J=8.20 Hz), 7.39-7.47 (2 H, m), 7.53 (1 H, t, J=7.91 Hz), 8.20 (2 H, s), 10.07 (1 H, t, J=6.24 Hz). LCMS (10 cm_apci_formic) tR 4.14 min; m/z 534/536/538 [M−H]−.

1. stirringthe reaction was stirred at 50° C. for 5 h
2. waitbefore standing at room temperature overnight
3. customthe organic phase was separated
4. customevaporated to dryness
5. customto give a yellow oil
6. customThis was purified by preparative HPLC