Dichloromethane → n-{1-(Difluoromethoxy)-6-[3-(3-methoxypropyl)phenyl]-6h-benzo[c]chromen-8-yl}methanesulfonamide

Participants

Reaction Conditions

Reaction Steps

A solution of allylmethylether (0.015 g, 0.2 mmol) and 9-BBN (0.4 mL of 0.5M solution in THF, 0.2 mmol) was shaken for 3 hours at 65° C, cooled down to 23° C., treated with solution of Example 103 (0.05 g, 0.10 mmol), [1,1′-Bis(diphenylphosphino)-ferrocene]dichloropalladium(II), complex with dichloromethane (0.004 g, 0.005 mmol), and sodium methoxide (0.016 g, 0.3 mmol) in THF (1 mL), shaken at 65° C. for 15 hours, cooled down to 23° C., treated with water (50 mL), and extracted with ethyl acetate(3×50 mL). The combined extracts were dried (MgSO4), filtered and concentrated under reduced pressure. The concentrate was purified by HPLC with aqueous 0.1% TFA and CH3CN to provide the titled compound. 1H NMR (300 MHz, DMSO-d6) δ 9.98 (s, 1H), 8.15 (d, J=9 Hz, 1H), 7.07-7.56 (m, 7H), 6.87-6.92 (m, 3H), 6.25 (s, 1H), 3.24 (t, J=6 Hz, 2H), 3.14 (s, 3H), 3.01 (s, 3H), 2.56 (t, J=7 Hz, 2H), 1.72 (m, J=7 Hz, 2H); MS (ESI(−)Q1MS m/z 488 (M−H).

Provenance & Evidence