Synthesis of N- (Aminoethyl) Azoles Under Phase Transfer Catalysis

N-Hydroxy-3-phenyl-2-propenamides as Novel Inhibitors of Human Histone Deacetylase with in Vivo Antitumor Activity: Discovery of (2E)-N-Hydroxy-3-[4-[[(2-hydroxyethyl)[2-(1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2-propenamide (NVP-LAQ824)

“…3-[4-[[[2-(9 H -Carbazol-9-yl)ethyl]amino]methyl]phenyl]-N-hydroxy-(2 E )-2-propenamide 13b. Following Method B, 9 H -carbazole-9-ethanamine hydrobromide (919 mg, 3.16 mmol), 1.4 equiv of Et 3 N, 10 (500 mg, 2.63 mmol), and NaBH(OAc) 3 (1.4 equiv) were reacted in DCE to afford 555 mg (47%) of 3-[4-[[[2-(9 H -carbazol-9-yl)amino]methyl]phenyl]-(2 E )-2-propenoic acid methyl ester: 1 H NMR (DMSO -d 6 ) δ 2.90 (t, 6.6 Hz, 2H), 3.72 (s, 5H), 4.48 (t, 6.6 Hz, 2H), 6.59 (d, 15.8 Hz, 1H), 7.19 (t, 7.0 Hz, 2H), 7.29 (d, 8.3 Hz, 2H), 7.44 (t, 7.7 Hz, 2H), 7.62 (m, 5H), 8.14 (d 7.9, 2H); 13 C NMR (DMSO -d 6 ) δ 43.00, 47.54, 51.38, 52.73, 109.72, 117.47, 119.03, 120.59, 122.42, 125.97, 128.60, 128.71, 132.77, 140.55, 143.85, 144.84, 176.14; m / z 385 (MH + ). Following Method E, the ester (405 mg, 1.05 mmol) was converted to the hydroxamate which was purified by RPHPLC to afford 13b as the TFA salt which was neutralized and treated with 1 equiv of lactic acid to provide 13b as the lactate salt (190 mg, 40%): retention time System 3 = 16.82 min, retention time System 4 = 28.11 min; 1 H NMR (DMSO -d 6 ) δ 1.26 (d, 6.8 Hz, 3H lactate), 3.26 (br s, 2H), 4.04 (q, 6.8 Hz, 1H lactate), 4.12 (br s, 1H), 4.67 (m, 1H), 6.52 (d, 15.8 Hz, 1H), 7.23 (t, 7.35 Hz, 2H), 7.48 (m 5H), 7.62 (m 4H), 8.16 (d, 7.9 Hz, 2H); 13 C NMR (DMSO -d 6 ) δ 20.91 (lactate), 45.65, 51.02, 66.21 (lactate), 109.49, 119.56, 120.78, 122.72, 126.24, 128.02, 130.31, 135.30, 138.06, 140.27, 162.94, 176.86 (lactate); m / z 386 (MH + ); HRMS (MH + ) calcd for C 24 H 24 N 3 O 2 , 386.1892, found 386.1869; mp 169.5−185.4 °C; Anal.…”

Metal Halide/N‐Donor Organic Ligand Hybrid Materials with Confined Energy Gaps and Emissions

“…The synthesis of compounds 1 – 4 is outlined in Scheme . The AEC ligand was prepared by a phase‐transfer catalysis reaction,8 and the product was purified by vacuum sublimation. ZnCl 2 , ZnI 2 , CdI 2 , and HgI 2 were treated with AEC in a 1:2 ratio in acetonitrile.…”

“…N ‐(2‐Aminoethyl)carbazole (AEC): The organic ligand was synthesized by following a literature procedure 8. The product was purified by gradient‐temperature sublimation.…”

Organocatalytic Enantioselective Multicomponent Synthesis of Pyrrolopiperazines

“…(3)]. The key features of the present transformation are: (i) it represents the first example of an enantioselective multicomponent MAPS sequence, with very simple operating conditions; (ii) the three reaction partners are commercially available or easily prepared;19 (iii) the products are formed in interesting chemical yields for a multicomponent reaction that uses fragile pyrrole substrates and creates four new bonds and two cycles; (iv) excellent enantioselectivities (>90% ee ) are uniformly observed on a wide range of diversified substrates; (v) in most cases, the two diastereomers of the product can be separated by traditional flash chromatography, allowing for the fast generation of molecular diversity.…”