反应详情

1-Chloro-2-fluoro-4-(methyloxy)-5-nitrobenzene (2.0 g, 9.7 mmol), from a different batch than previously described, was dissolved in DMSO (50 mL) and K2CO3 (6.7 g, 49 mmol), and phenylmethyl 4-(4-piperidinyl)-1-piperazinecarboxylate bis(trifluoroacetate) salt (5.1 g, 9.7 mmol) were added. Reaction was stirred overnight. Poured into H2O and extracted (2×) with EtOAc. Combined organic layers were back-extracted (5×) with H2O and then dried over MgSO4, filtered, concentrated on to silica gel and flash chromatographed to give the title compound of step C (4.95 g, 100%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.96 (s, 1H), 7.00-7.52 (m, 5H), 6.76 (s, 1H), 5.03 (s, 2H), 3.90 (s, 3H), 3.54 (d, J=12.1 Hz, 2H), 3.17-3.47 (m, 4H), 2.76 (t, J=11.4 Hz, 2H), 2.23-2.63 (m, 5H), 1.82 (d, J=11.5 Hz, 2H), 1.54 (qd, J=11.7, 3.0 Hz, 2H).

1. customReaction
2. extractionextracted (2×) with EtOAc
3. extractionCombined organic layers were back-extracted (5×) with H2O
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated on to silica gel and flash
7. customchromatographed