Tetrahydrofuran → HCID 68699889, compound

Participants

Reaction Steps

A dry round bottom flask was charged with 6-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one (as prepared in Example 40, 0.300 g, 1.19 mmol), 1,3-Dimethyl-2H-pyrazole-5-carbaldehyde (0.191 g, 1.91 mmol) and acetic acid (0.3 mL). The mixture was allowed to stir for 4 h at room temperature. A 1M solution of sodium cyanoborohydride in THF (3.57 mL, 3.57 mmol) was then added and the mixture was allowed to stir for 45 minutes. The reaction mixture was poured into H2O (100 mL) and allowed to stir for 15 minutes. The resulting suspension was vacuum filtered and the filtrate was extracted with EtOAc (3ט100 mL). The organic layers were combined, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to afford a yellow oil. The yellow oil was then chromatographed over silica which had been previously neutralized by flushing the column with the purification eluant (97/3, chloroform/methanol w/0.5% NEt3) several times. This chromatographic purification resulted in the isolation of pure 6-{3-[(2,5-Dimethyl-2H-pyrazol-3-ylmethyl)-amino]-benzoyl}-1,3-dihydro-indol-2-one in 30% yield (0.128 g, 0.357 mmol).

Provenance & Evidence