Sodium Carbonate → HCID 57942668, compound

Participants

Reaction Conditions

Reaction Steps

To 100B (3.48 g, 11.8 mmol), 3A (3.0 g, 14.2 mmol) and sodium carbonate (23.7 mL, 2M, 47.4 mmol) in 1,2 dimethoxyethane (100 mL, flushed and degassed (3×) with nitrogen) was added Pd(PPh3)4 (2.74 g, 2.37 mmol). The reaction was heated to 97° C. for 3 h. The catalyst was filtered over celite and washed with ethyl acetate. The organic layer was washed with water, brine and then dried over sodium sulfate. The solvent was removed and the crude residue was purified by flash column chromatography to give 4.11 g of product 10° C. (91% yield). 1H NMR (400 MHz, Methanol-d4) δ ppm 1.09 (t, J=7.46 Hz, 3H) 1.25 (s, 9H) 2.87-3.04 (m, 2H) 6.24-6.44 (m, 2H) 7.46 (dd, J=3.30, 1.83 Hz, 1H) 8.24 (d, J=2.20 Hz, 1H) 8.31 (d, J=8.56 Hz, 1H) 8.45 (dd, J=8.80, 2.45 Hz, 1H).

Provenance & Evidence