2-Methoxyethanol → HCID 58266777, compound

Participants

Reaction Steps

A solution of 9-benzenesulfonyl-3-bromo-5-hydroxy-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (145 mg, 0.3 mmol), 2-methoxyethanol (158 μL, 2.0 mmol) and triphenylphosphine (525 mg, 2.0 mmol) in anhydrous DMF (1.25 mL) was treated with diethyl azodicarboxylate (0.315 mL, 2.0 mmol) and the mixture stirred at ambient temperature for 30 min then left to stand for 4 days. The mixture was diluted with ethyl acetate (20 mL) and washed with brine (3×10 mL) then the aqueous phase was extracted with ethyl acetate (10 mL). The combined organic phase was dried over magnesium sulfate and concentrated in vacuo. The resultant residue was purified by flash chromatography (silica, 5 g column, Si-SPE, 0-100% ethyl acetate in DCM) to afford the title compound (35 mg, 23%). 1H NMR (CDCl3, 300 MHz): 9.58 (s, 1H), 8.97 (d, J=2.3 Hz, 1H), 8.76 (d, J=2.3 Hz, 1H), 8.26-8.18 (m, 2H), 7.68-7.60 (m, 1H), 7.57-7.47 (m, 2H), 4.74-4.69 (m, 2H), 3.89-3.80 (m, 2H), 3.49 (s, 3H).

Provenance & Evidence