Dichloromethane → HCID 54679007, compound

Participants

Reaction Steps

To a suspension of 50 mg (0.14 mmol) of 3-(4-benzyloxy-phenyl)-4-hydroxy-7H-thieno[2,3-b]pyridin-6-one from Example 7D in 2 mL of CH2Cl2 was added 38 mg (0.28 mmol) of N-chlorosuccinimide. The suspension became a homogeneous solution, and was stirred open to the air while the solvent was allowed to evaporate to dryness over two days. The residue was redissolved in 2 mL of CH2Cl2, and 100 μL (0.72 mmol) of iodotrimethylsilane was added. After 18 h, the reaction was concentrated in vacuo. The residue was dissolved in ethyl acetate (5 mL) and extracted with 5% NaHSO3(aq.) (1×2 mL) to discharge the 12 color, then with brine (1×2 mL), dried over MgSO4, filtered, and concentrated to an oil. This was purified via reverse phase HPLC (0 to 70% CH3CN/0.1% aq. TFA gradient) to give 16 mg (34%) of a solid as the titled compound. MS (ESI) m/e 327.8, (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 6.79 (m, 2H) 7.15 (m, 2H) 9.54 (s, 1H) 10.84 (s, 1H) 12.40 (bs, 1H).

Provenance & Evidence