Cesium carbonate → methyl 1-[3-(benzyloxy)propyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylate

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Reaction Conditions

Reaction Steps

A mixture of methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylate (Compound 38F, 600 mg, 2.39 mmol) and 1-bromo-3-benzyloxypropane (575 mg, 2.51 mmol) in DMF (2.19 mL) was charged with cesium carbonate (778 mg, 2.39 mmol). The reaction mixture was allowed to stir at 70° C. for 16 hrs. The reaction mixture was diluted with water and then extracted with EtOAc (2×). The organic layer was washed with water (2×), brine (1×), dried over Na2SO4, filtered, concentrated in vacuo and purified using a Teledyne ISCO Combiflash® Rf system [0→4% Ethanol in DCM] to afford 442 mg of the title compound (46%). 1H NMR (400 MHz, CD3OD) δ 7.26-7.37 (m, 5H), 7.25 (d, J=1.8 Hz, 1H), 7.17 (d, J=1.8 Hz, 1H), 4.45 (s, 2H), 4.42 (t, J=6.8 Hz, 2H), 3.78 (s, 3H), 3.38 (t, J=5.9 Hz, 2H), 2.01 (t, J=6.2 Hz, 2H), 1.31 (s, 12H). MS (ESI): m/z 440.59 [M+H]+. UPLC: tR=1.60 min (UPLC-TOF: polar—2 min).

Provenance & Evidence