Sodium Carbonate → HCID 86345854, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of compound 3a (100 mg, 0.228 mmol), compound 85b (88.2 mg, 0.274 mmol), PdCl2(dppf)-DCM (5.6 mg, 0.0068 mmol), and Argon-degassed aqueous 2M Na2CO3 (0.570 mL, 1.14 mmol) in Argon-degassed 1,4-dioxane (4 mL) was further degassed with Argon for 2 min and then stirred at 90° C. for 5 h. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure to a brown oil which was purified by flash column chromatography on silica gel (0-100% EtOAc-heptane, followed by 100% EtOAc) to afford a colorless resin. The residue obtained was further purified by flash column chromatography (100% EtOAc, followed by 0-10% MeOH-EtOAc) to afford a colorless oil, which was triturated with EtOAc-heptane (1:3) and concentrated under reduced pressure to give the title compound 31 as an off-white crystalline solid. 1H-NMR (CDCl3; 400 MHz): δ (ppm) 8.01-8.08 (m, 2H), 7.79 (d, J=8.1 Hz, 1H), 7.67-7.73 (m, 1H), 7.48-7.54 (m, 1H), 7.30-7.38 (m, 4H), 7.24 (s, 1H), 6.98 (d, J=8.6 Hz, 2H), 4.16-4.23 (m, 6H), 3.91 (t, J=4.8 Hz, 2H), 3.82-3.86 (m, 4H), 3.73-3.78 (m, 2H), 3.59-3.63 (m, 2H), 3.41-3.42 (m, 3H), 3.38-3.44 (m, 2H), 3.27-3.33 (m, 2H); Mass spectrum (LCMS, ESI pos.): Calcd. for C32H35N5O4, 554.3 (M+H). found 554.5.

Provenance & Evidence