Triethylamine → HCID 68108868, compound

Participants

Reaction Steps

To a solution of the product obtained from step A (80 mg, 0.16 mmol) in anhydrous acetonitrile (1.5 mL) was added triethylamine (45 μL, 0.32 mmol) followed by dimethylamine hydrochloride (20 mg, 0.24 mmol) and benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphoniumhexafluorophosphate (106 mg, 0.24 mmol). After stirring at ambient temperature for 12 h, the resulting solution was concentrated to dryness in vacuo. The reaction mixture was diluted with ethyl acetate (20 mL), washed sequentially with saturated aqueous NaHCO3 (10 mL) and brine (10 mL), and dried over anhydrous MgSO4. After filtration, the filtrate was concentrated in vacuo to give the crude product which was purified by flash column chromatography (SiO2, 9:1 to 3:2 hexanes/ethyl acetate) to afford tert-butyl 6-chloro-1-(dimethylcarbamoyl)-8-(phenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (60 mg, 71%) as a colorless oil: 1H NMR (CDCl3, 400 MHz) δ 7.93-7.77 (m, 4H), 7.57-7.48 (m, 3H), 6.19 (s, 1H), 4.53-4.27 (m, 1H), 3.76-3.62 (m, 2H), 3.43 (s, 3H), 3.02 (s, 3H), 2.85-2.80 (m, 1H), 1.49 (s, 9H).

Provenance & Evidence