Peracetic Acid → HCID 71678736, compound

Participants

Reaction Conditions

Reaction Steps

To a solution containing 202 mg (0.60 mmol) of 5-Bromo-1,4-dimethyl-6-octyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine in 5 mL of THF was added 90 μL (69.7 mg, 0.60 mmol) of tetramethylethylenediamine (TMEDA) at −78° C. followed by 0.75 mL (1.20 mmol) of n-BuLi (1.6 M in hexanes). After 30 min, 147 μL (137 mg, 1.32 mmol) of trimethoxy boron was added and the resulting mixture was stirred for another 1 h. To the reaction mixture was added dropwise 277 μL (100 mg, 314 mg total solution mg, 1.32 mmol) of peracetic acid (32% wt) and the solution was then warmed to 0° C. The mixture was diluted by 20 mL of water and extracted with three 25-mL portions of EtOAc. The combined organic layer was washed with brine, dried over anhydrous MgSO4, filtered, and concentrated under diminished pressure. The resulting oil was dissolved in 10 mL of CH2Cl2 at 0° C., followed by the addition of 485 μL (352 mg, 3.48 mmol) of triethylamine, 6.1 mg (0.05 mmol) of DMAP and 164 μL (177 mg, 1.74 mmol) of acetic anhydride. The reaction was stirred at room temperature for 1 h and quenched by the addition of 10 mL of sat aq. NH4Cl. The solution was extracted with three 30-mL portions of EtOAc. The combined organic layer was washed with brine, dried over anhydrous MgSO4, filtered, and concentrated under diminished pressure. The residue was purified via flash chromatography on a silica: gel column (46×2.5 cm). Step gradient elution with 1:10→1:4 ethyl acetate-hexanes as eluent gave 1d as a yellow oil: yield 92 mg (48%); silica gel TLC Rf 0.22 (3:7 ethyl acetate-hexanes); 1H NMR (CDCl3) δ 0.76 (t, 2H, J=7.2 Hz), 1.12-1.22 (m, 10H), 1.55 (quint, 2H, J=8.0 Hz), 1.88 (s, 3H), 2.20 (s, 3H), 2.35 (t, 2H, J=8.0 Hz), 2.75 (t, 2H, J=8.4 Hz), 2.88 (s, 3H), 3.42 (t, 2H, J=8.4 Hz).

Provenance & Evidence