Cesium carbonate → HCID 58015564, compound

Participants

Reaction Steps

To a solution of 2-bromo-5-(1H-indazol-5-yl)furo[3,2-c]pyridin-4(5H)-one (1.13 g, 3.41 mmol) in DMSO (10.5 mL) was added methyl bromoacetate (0.64 mL, 6.8 mmol) and Cs2CO3 (4.44 g, 13.6 mmol). The reaction mixture was stirred at ambient temperature for 18 h; then additional methyl bromoacetate (0.30 mL) was added. After 3 h, additional methyl bromoacetate (0.30 mL) was added. The reaction mixture was stirred for 3.5 h and then the reaction mixture was diluted with H2O (50 mL) and extracted with CH2Cl2 (4×25 mL). The extracts were washed with brine (3×25 mL), dried (Na2SO4) and concentrated. Purification by flash chromatography (silica gel, CH2Cl2/MTBE, 4:1) yielded the title compound (0.77 g, 56%) as a light yellow solid: 1H NMR (500 MHz, CDCl3) δ 8.10 (s, 1H), 7.73 (s, 1H), 7.43 (s, 2H), 7.30 (d, J=7.5 Hz, 1H), 6.97 (s, 1H), 6.60 (d, J=7.0 Hz, 1H), 5.21 (s, 2H), 3.77 (s, 3H).

Provenance & Evidence