Triethylamine → HCID 53907499, compound

Participants

Reaction Conditions

Reaction Steps

3-(3,5-Dibromo-4-hydroxy-benzylidene)-2-oxo-2,3-dihydro-1H-indol-5-carboxylic acid (0.34 9, 0.77 mmol) (Example 156) and ethanofamine (0.08 g, 1.3 mmol) were dissolved in DMF (2 mL) and cooled with stirring to 5° C. Diethyl cyanophosphonate (0.172 g, 1 mmol), followed by triethylamine (0.25 g, 2.5 mmol) were added and stirring continued for 0.5 h at 50° C. and then the reaction allowed to warm to room temperature. After 1.5 h the reaction was quenched with water (10 mL) and extracted four times with a 4/1 mixture of chloroform/isopropanol (25 mL). The organic phases were combined, dried over magnesium sulfate and concentrated to dryness. Recrystalization from ethanol gave 22 mg of 3-(3,5-dibromo-4-hydroxy-benzylidene)-2-oxo-2,3-dihydro-1H-indol-5-carboxylic acid (2-hydroxyethyl)amide; 1H-NMR (DMSO-d6): δ10.9 (s, 1H), 10. 7 (bs, 1H), 8.81 (s, 2H), 8.25 (t, J=5.6 Hz, 1H), 8.19 (s, 1H), 7.77 (s, 1H), 7.72 (d, J=8.0 Hz, 1 H), 6.86 (d, J=8.0 Hz, 1 H), 4.73 (bs, 1H), 3.52 (m, 2H), 3.37 (m, 2H). Mass spectrum (negative ion electrospray): m/z=479 (M−1, 22%), 481 (M−1, 35%), 483 (M−1, 30%).

Provenance & Evidence