Sodium Carbonate → 2-Cyclohex-1-enyl-3-nitro-pyridine

Participants

Reaction Conditions

Reaction Steps

A solution of 1.00 g (6.31 mmol) of 2-chloro-3-nitro-pyridine in toluene (50 mL) and EtOH (25 mL) was treated with 1.58 g (7.57 mmol) of 2-cyclohex-1-enyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane and 25.2 mL (50.4 mmol) of 2.0 M aqueous Na2CO3. The mixture was degassed via sonication, placed under Ar, treated with 729 mg (0.631 mmol) of Pd(PPh3)4, and heated to 80° C. for 16 h. The mixture was diluted with EtOAc (100 mL) and washed with water (1×75 mL). The organic layer was dried (MgSO4) and concentrated in vacuo. Silica gel chromatography of the residue on a 50-g Varian MegaBond Elut SPE column with CH2Cl2 afforded 497 mg (39%) of the title compound as a yellow solid: 1H-NMR (CD3OD; 400 MHz): δ 8.70 (dd, 1H, J=5.2, 1.6 Hz), 8.20 (dd, 1H, J=8.4, 1.6 Hz), 7.51-7.46 (m, 1H), 5.81 (sept, 1H, J=2.4 Hz), 2.44-2.37 (m, 2H), 2.19-2.12 (m, 2H), 1.84-1.76 (m, 2H), 1.74-1.66 (m, 2H).

Provenance & Evidence