tert-Butyl acetate → HCID 58095078, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N,N-diisopropylethylamine (6.6 mL, 38 mmol) in THF (50 mL), n-butyllithium (1.6 mol/L in hexane solution: 24 mL, 38 mmol) was added at −40° C. After being stirred for 30 min, the mixture was cooled to −78° C. To the mixture, was added 1,1-dimethylethyl acetate (5.28 mL, 62.8 mmol) and the mixture was stirred for 40 min at −78° C. To the mixture, was added ethyl 2-methylpyrazolo[1,5-a]pyridine-3-carboxylate (3.64 g, 17.8 mmol) and the mixture was stirred for 1 h at rt. To the mixture, were added a saturated aqueous solution of ammonium chloride (300 mL) and EtOAc (300 mL) and the resulting biphasic mixture was vigorously stirred for 30 min. The organic phase was washed with brine and then dried over anhydrous magnesium sulfate. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure. Column chromatography was performed to yield the title compound (1.58 g, 32%) as a pale yellow syrup. 1H NMR (300 MHz, d6-DMSO) δ: 8.78 (d, J=7.0 Hz, 1H), 8.19-8.10 (m, 1H), 7.61 (ddd, J=8.7, 7.2 and 1.1 Hz, 1H), 7.15 (td, J=7.0, 1.1 Hz, 1H), 3.91 (s, 2H), 2.61 (s, 3H), 1.42 (s, 9H).

Provenance & Evidence