Sodium Carbonate → HCID 59452826, compound

Participants

Reaction Conditions

Reaction Steps

4-Chloro-1-nitro-2-propylbenzene (J. Organometallic Chem. 2001, 624(1-2), 167-171) (0.299 g, 1.50 mmol), 1,1-dimethylethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate (0.553 g, 1.79 mmol), Na2CO3 (0.509 g, 4.80 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.0620 g, 0.0900 mmol) in dioxane (6 mL) and H2O (3 mL) was degassed for 10 min. The mixture was heated at 80° C. overnight. The reaction was filtered through Celite®, washed with EtOAc and H2O, dried (MgSO4), concentrated and purified by flash chromatography to provide the title compound of step A (0.451 g, 1.30 mmol, 87%). 1H NMR (400 MHz, CDCl3) δ ppm 0.97 (t, J=7.3 Hz, 3H), 1.46 (s, 9H), 1.65 (sextet, J=7.5 Hz, 2H), 2.50 (br. s., 2H), 2.83-2.88 (m, 2H), 3.62 (t, J=5.7 Hz, 2H), 4.08 (q, J=2.7 Hz, 2H), 6.14 (br. s., 1H), 7.25-7.29 (m, 2H), 7.87 (d, J=7.9 Hz, 1H).

Provenance & Evidence