Toluene → HCID 54466218, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(3,5-Dibromo-4-hydroxy-benzylidene)-5-iodo-1,3-dihydro-indol-2-one (210 mg, 0.40 mmol) in 20 ml of THF under nitrogen was added 1M potassium t-butoxide in THF (0.40 ml, 0.40 mmol) dropwise via syringe. The solution was cooled to 0° C. and 1.97M phosgene in toluene (0.21 ml, 0.41 mmol) was added dropwise via syringe and the reaction mixture was stirred 10 minutes. 2-(2-Aminoethoxy)ethanol (40 μl, 0.40 mmol) was then added via syringe followed by N-methyl morpholine (˜45 mg, ˜45 mmol). The reaction mixture was stirred 10 minutes at 0° C. and then allowed to warm to room temperature. The solution was diluted with an equal volume of ether, filtered through a fine frit to clarify, and further diluted with 10 ml of ether. The product was then precipitated by the addition of ˜80 ml of hexanes and was filtered and washed with more hexanes to give 0.21 g (79%) of the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6) 6: 10.77 (s, 1H), 8.24 (t, J=5.6 Hz, 1H), 8.02 (s, 2H), 7.6 (s, 1H), 7.57 (s, 1H), 7.55 (dd, J=8.2, 1.6 Hz, 1H), 6.71 (d, J=8.2 Hz, 1H), 4.58 (br t, 1H), 3.52-3.42 (m, 6H), 3.27-3.20 (m, 2H). ESI-MS m/z 673, 675, 677 (M+23). Anal. Calcd. for C20H17Br2IN2O5: C, 36.84; H, 2.63; N, 4.30. Found: C, 36.75; H, 2.60; N, 4.22.

Provenance & Evidence