Cesium carbonate → HCID 59442054, compound

Participants

Reaction Conditions

Reaction Steps

To 5-chloro-2-nitrobenzaldehyde (10.0 g, 54.0 mmol, Aldrich) in dioxane (300 mL) was added 1-(1-methylethyl)piperazine (13.8 g, 108.0 mmol, Aldrich), XANTPHOS (3.1 g, 5.4 mmol, Aldrich), and Cs2CO3 (35.2 g, 108.0 mmol, Aldrich). The mixture was bubbled with N2 for 15 min prior to the addition of Pd2(dba)3 (2.5 g, 2.7 mmol, Aldrich). The reaction was stirred at 100° C. for 5 h. Ethyl acetate (150 mL) was used to dilute the reaction mixture, followed by the addition of water (100 mL). After partitioning, extraction with Ethyl acetate (2×75 mL), drying (Na2SO4), concentration, and silica gel chromatography afforded 5-[4-(1-methylethyl)-1-piperazinyl]-2-nitrobenzaldehyde (1.5 g, 10% yield). 1H NMR (400 MHz, CDCl3) δ ppm 1.08 (d, J=6.6 Hz, 6 H), 2.62-2.69 (m, 4 H), 2.70-2.79 (m, 1 H), 3.46-3.51 (m, 4 H), 6.93 (dd, J=9.2, 2.9 Hz, 1 H), 7.13 (d, J=2.9 Hz, 1 H), 8.09-8.12 (m, 1 H), 10.53 (s, 1 H).

Provenance & Evidence