Hydrochloric Acid → (+/-)-methyl 6-chloro-5-(4-{[trans-2-hydroxycyclopentyl]oxy}phenyl)-1H-indole-3-carboxylate

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A mixture of methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylate (92.6 mg, 0.288 mmol) and (±)-trans-2-(4-bromophenoxy)-cyclopentanol (37 mg, 0.14 mmol) in ethanol (0.2 mL), toluene (0.3 mL), and 2M aqueous potassium carbonate (0.288 mL, 0.576 mmol) was sealed in a microwave vial and degassed with nitrogen for 10 minutes. [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (10.2 mg, 0.014 mmol) was added, and the reaction mixture was resealed and heated to 90° C. in an oil bath for 1 hour. The reaction mixture was cooled to room temperature and poured into 0.5N HCl (10 mL). The product was extracted with ethyl acetate (3×10 mL), and the combined organic layers were dried over sodium sulfate, filtered and evaporated. The crude product was purified using silica gel chromatography (4:1 to 1:4 heptane/ethyl acetate) to give the title compound (49 mg, 88%) as a white solid. MS (ES−) 384.2 (M−H)−. 1H NMR (500 MHz, CD3OD) δ 8.00 (s, 1H), 7.98 (s, 1H), 7.57 (s, 1H), 7.34 (d, J=8.5 Hz, 2H), 6.99 (d, J=8.5 Hz, 2H), 4.57 (br. s., 1H), 4.26 (br. s., 1H), 3.87 (s, 3H), 2.25-2.15 (m, 1H), 2.10-2.02 (m, 1H), 1.91-1.77 (m, 3H), 1.72-1.62 (m, 1H)

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