Sodium Hydroxide → HCID 67441940, compound

Participants

Reaction Steps

A mixture of EXAMPLE 23I (1.7 g, 2.63 mmol) in dioxane (150 ml) was heated with NaOH (0.53 g, 13.2 mmol) at 50° C. for 4 hours. After cooling, the reaction mixture was partitioned between ethyl acetate (300 mL) and brine (200 mL). The organic phase was washed with brine (200 mL), dried over anhydrous Na2SO4, filtered and concentrated. The crude material was purified by flash chromatography (2% methanol in CH2Cl2) to afford the title compound. LC-MS (ESI): m/z 506 (M+H), RT: 1.53 min; 1H NMR (400 MHz, dimethylsulfoxide-d6): δ 3.75 (s, 3H), 3.77 (s, 3H), 3.92 (s, 2H), 4.88 (s, 1H), 4.99 (s, 1H), 6.46 (s, 1H), 6.50 (s, 1H), 6.56 (d, J=8.0 Hz, 3H), 7.07 (d, J=8.4 Hz, 1H), 7.06 (d, J=8 Hz, 2H), 7.14 (d, J=3.2 Hz, 1H), 7.31 (s, 1H), 7.71 (s, 1H), 7.85 (d, J=1.2 Hz, 1H), 8.22 (d, J=8.0 Hz, 1H), 8.26 (d, J=4.8 Hz, 1H), 11.75 (br s, 1H).

Provenance & Evidence