Potassium Carbonate → Formate

Participants

Reaction Conditions

Reaction Steps

(2-bromoethoxy)-tert-butyl-dimethylsilane (104 mg, 435 μmol) was added to a suspension of 2-ethyl-4-(5-{3-[(ethyl-methyl-amino)-methyl]-5-methyl-phenyl}-[1,2,4]oxadiazol-3-yl)-6-methyl-phenol (53 mg, 145 μmol) and K2CO3 (60 mg, 435 μmol) in acetonitrile (2 mL). The mixture was stirred at 70° C. for 16 h before it was filtered. The filtrate was diluted with 1N aq. HCl (0.1 mL) and 2N aq. HCl (0.1 mL). The mixture was allowed to stand at rt for 10 min before the solvent was removed in vacuo. The crude product was purified by prep. HPLC to give the title compound as a formate salt in the form of a white lyphilisate (29 mg). LC-MS: tR=0.59 min; [M+1]+=410.26; 1H NMR (D6-DMOS): δ 1.06 (t, J=7.3 Hz, 3H), 1.23 (t, J=7.3 Hz, 3H), 2.15 (s, 3H), 2.36 (s, 3H), 2.42-2.48 (m, 5H), 2.75 (q, J=7.5 Hz, 2H), 3.56 (s, 2H), 3.73-3.77 (m, 2H), 3.84-3.89 (m, 2H), 7.47 (s, 1H), 7.80 (s, 2H), 7.90 (s, 1H), 7.92 (s, 1H), 8.17 (s, 1H, formate).

Provenance & Evidence