Ethyl acetate hexane → HCID 45095432, compound

Participants

Reaction Steps

A solution of N-(2-ethylpyrazolo[1,5-a]pyridin-3-yl)-N-(3-fluoropropyl)-2-methoxyacetamide (1.00 g, 3.39 mmol) in THF (12 mL) was added to a slurry of LAH (1.05 g, 27.7 mmol) in THF (6 mL) and the reaction was stirred at room temperature for 3.25 hours. The reaction was cooled to 0° C. and quenched with water (1 mL), 15% NaOH (3 mL) and water (3 mL). The mixture was filtered through diatomaceous earth and the filtrate was extracted with CH2Cl2, dried over MgSO4 and concentrated in vacuo to give a brown oil which was subjected to column chromatography (50% ethyl acetate/hexane) to give 0.568 g (75%) of yellow oil as the title compound: 1H NMR (400 MHz, DMSO-d6) δ 8.38 (d, J=7.0 Hz, 1H), 7.49 (d, J=9.0 Hz, 1H), 6.98–6.94 (m, 1H), 6.63–6.60 (m, 1H), 4.52 (dt, J=47.5, 5.9 Hz, 2H), 4.10 (br, 1H), 3.04 (t, J=6.9 Hz, 2H), 2.70 (q, J=7.6 Hz, 2H), 1.89–1.76 (m, 2H), 1.24 (t, J=7.6 Hz, 3H); 13C NMR (100 MHz, DMSO-d6) δ 148.8, 133.1, 128.1, 120.7, 118.5, 116.0, 110.1, 81.1 (d, J=160.6 Hz), 45.6 (d, J=5.2 Hz), 30.8 (d, J=19.2 Hz), 18.6, 13.4; 19F NMR (376 MHz, DMSO-d6) −219.0 (m); HRMS (FAB) calcd for C12H16FN3+H 222.1406. found 222.1403.

Provenance & Evidence