Nitrogen → HCID 11231903, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of Example 55A (301 mg, 1.16 mmol), 4-phenoxyphenylboronic acid (271 mg, 1.27 mmol) and Na2CO3 (403 mg, 4.75 mmol) in DME (10 mL), water (4.8 mL), and ethanol (2.4 mL) was degassed with N2 for 45 minutes, treated with Pd(PPh3)4 (120 mg), and heated to 80° C. overnight. The suspension was cooled to room temperature, poured into water, and extracted with ethyl acetate. The combined extracts were dried (Na2SO4), filtered, and concentrated. The concentrate was triturated with warm ethanol to give 183 mg of the desired product. 1H NMR (300 MHz, DMSO-d6) δ 4.51 (s, 2H); 7.07–7.13 (m, 3H); 7.20 (t, J=7.5 Hz, 1H); 7.33 (t, J=7.1 Hz, 1H); 7.38–7.47 (m, 3H); 7.59 (t, J=7.5 Hz, 1H); 7.62–7.69 (m, 3H); 8.69 (s, 1H); MS (ESI(+)) m/e 302.1 (M+H)+.

Provenance & Evidence