Diisopropylamine → HCID 57494707, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of diisopropylamine (1.09 mL, 7.8 mmol) and N,N,N,N-tetramethylenediamine (1.17 mL, 7.8 mmol) in dry THF (19 mL) at −20° C. was added n-BuLi (5.54 mL, 1.4 M in hexane) and the resulting mixture was stirred at −20° C. for 5 minutes. Then a mixture of 2[(4-chloro-2-methylphenyl>(4-methoxybenzyl)-amino]-N,N-diethylbenzamide (189JO26) (1.36 g, 3.1 mmol) in dry THF (38 mL) was added and the resulting mixture was stirred at −20° for 4 h. The reaction was quenched by addition of saturated aqueous NH4Cl-solution. The mixture was diluted with EtOAc, washed with water, dried (Na2SO4), concentrated, and flash chromatographed (SiO2, toluene:heptane, 7:1-1:0) to give 665 mg (59%) of the title compound (189JO27). 1H NMR (CDCl3) δ 8.15 (dd, 1 H, J=1.8, 8.0 Hz), 7.43 (m, 1 H), 7.24 (m, 4 H), 7.17 (d, 1 H, J=8.6 Hz), 7.12 (dd, 1 H, J=2.4, 8.6 Hz), 7.00 (dt, 1 H, J=0.8, 7.0 Hz), 6.81 (m, 2 H), 5.09 (s, 2 H), 4.00 (s, 2 H), 3.75 (s, 3 H); 13C NMR (CDCl3) δ 190.3, 159.1, 149.5, 146.2, 134.1, 132.4, 131.3, 131.1, 129.1, 129.0, 128.6, 127.3, 126.4, 123.4, 121.0, 118.5, 114.2, 55.5, 19.3. MS (ESI) 364 (MH+).

Provenance & Evidence