Diisopropylethylamine → HCID 68282460, compound

Participants

Reaction Steps

To a solution of 5-bromopyrazolo[1,5-a]pyridine-3-carboxylic acid (I-25) (66 mg, 0.27 mmol) in DMF (3 mL) was added DIEA (0.14 mL) and HATU (0.10 g, 0.27 mmol). The reaction was stirred for 30 minutes at room temperature then bis(4-methoxybenzyl)amine (70 mg, 0.27 mmol) was added. Stirring was continued at room temperature for 12 hours. The reaction was diluted with EtOAc, washed with brine, dried over magnesium sulfate, filtered and reduced to dryness. The crude product was purified by flash column chromatography on silica with hexanes/EtOAc gradient as eluant to yield 5-bromo-N,N-bis(4-methoxybenzyl)pyrazolo[1,5-a]pyridine-3-carboxamide (I-26). 1H NMR (400 MHz, CDCl3) δ 8.50 (d, J=2.4 Hz, 1 H), 8.26 (dd, J=0.4, 7.2 Hz, 1 H), 7.88 (s, 1 H), 7.22 (d, J=8.0 Hz, 4 H), 7.00 (dd, J=2.0, 7.2 Hz, 1 H), 6.91 (d, J=8.4 Hz, 4 H), 4.67 (s, 4 H), 3.82 (s, 6 H). MS m/z 480.1, 482.1 (M+1)+.

Provenance & Evidence