Tetrahydrofuran → HCID 69739267, compound

Participants

Reaction Steps

A solution of 5.69 g (26.5 mmol) of methyl 2-chloro-3-nitrobenzoate and 6.00 g (29.1 mmol) of the boronic acid from Part A in 110 mL of THF was treated with 1.68 g of tetrakis(triphenylphosphine)palladium(0) followed by 29.1 mL (58.2 mmol) of 2.0 N Na2CO3. The mixture was flushed with a stream of N2 and heated to mild reflux for 48 hrs. The reaction was allowed to cool and was extracted with EtOAc (5×100 mL). The combined organic layers were washed sequentially with H2O, 1 N aq HCl, saturated aq NaHCO3, and H2O. The organic layers were dried over Na2SO4, filtered and concentrated in vacuo 12.4 g of crude material. The residue was purified by flash chromatography (SiO2; 30% hexanes in toluene to 100% toluene) to afford 3.88 g (43%) of the title compound. 1H NMR (DMSO-d6) δ 8.04 (dd, J=8.1 and 1.1 Hz, 1H), 7.94 (dd, J=7.7 and 1.1 Hz, 1H), 7.68-7.61 (m, 1H), 6.69-6.64 (m, 2H), 3.54 (m, 6H), 2.74-2.67 (m, 2H), 2.61-2.53 (m, 2H), 1.74-1.64 (m, 4H); IR (CHCl3) 2936, 1735, 1535, 1511, 1465, 1298, 1268, 1126 cm−1; FDMS 342 (M+1).

Provenance & Evidence