Diisopropylethylamine → HCID 58554133, compound

Participants

Reaction Steps

A solution of 2-chloro-4-cyanopyridine (1.00 g, 7.2 mmol), glycine tert-butyl ester (1.5 mL, 10.8 mmol) and DIEA (4.9 mL, 28.9 mmol) in anhydrous DMA (15 mL) was heated at 150° C. for 48 hours. The reaction mixture was diluted with Et2O (100 mL) and washed with water (2×50 mL) and brine (50 mL). The organic layer was dried (MgSO4) and the solvents were removed under reduced pressure. After purification by flash chromatography (silica, DCM), the title compound was obtained as a yellow oil. HPLC (Method A), Rt: 3.1 min (purity: 94%). UPLC/MS, M+(ESI): 178.0 ([M-tBu+2H]+), M−(ESI): 232.1. 1H NMR (DMSO-d6, 300 MHz) δ 8.15 (d, J=5.2 Hz, 1H), 7.44 (t, J=6.2 Hz, 1H), 6.93 (brs, 1H), 6.85 (dd, J=5.2, 1.3 Hz, 1H), 3.94 (d, J=6.2 Hz, 2H), 1.38 (s, 9H).

Provenance & Evidence