Sci. 2013, 14 3.7.three. Synthesis of 2-(2-[(2-iodo-4,5-dimethoxyphenyl)methyl]-4,5-dimethoxy phenyl) Acetate (DIV880, Figure 4)A total of 1.7 g (four.two mmol, 1 eq.) of compound two dissolved in 25 mL of acetic acid was added drop-wise to a answer of 1.77 g (six.three mmol, 1.five eq.) of chloramine T and 944 mg (six.3 mmol, 1.5 eq.) of sodium iodide in 25 mL of acetic acid stirred over 1 h. Right after two hours at space temperature, the mixture was poured into 20 mL of water and extracted 3 instances with ethyl acetate. The organic layer was washed twice with brine, dried over magnesium sulfate, and evaporated to dryness to yield 4.0 g of crude brownish material. Purification by chromatography on silica gel (eluant: heptane/AcOEt 8/2) resulted in 1.two g (55 ) of compound DIV880 as a yellow oil. 1H NMR (CDCl3) 7.29 (s, 1H), 6.81 (s, 1H), six.54 (s, 1H), 6.43 (s, 1H), 3.94 (s, 2H), three.91 (s, 3H), 3.88 (s, 3H), three.79 (s, 3H), three.68 (s, 3H), 3.45 (s, 2H), 1.44 (s, 9H). 13C-NMR ( (CDCl3) 170.9, 149.5, 148.0, 147.4, 135.7, 130.five, 125.five, 121.6, 113.9, 113.five, 112.8, 88.7, 80.7, 56.1, 55.8, 55.eight, 55.7, 43.two, 39.six, 28.0. LCUV (XTerra?MS C18 five ) rt = 13.476 min (285.5 nm) UV 99.8 . ESI [M + Na]+ = 551.35. three.8. Synthesis of SD6 three.359586-69-9 Data Sheet eight.1. Synthesis of N-[2-(5-methoxy-1H-indol-3-yl)ethyl]iodoacetamide (SD6), Route A N-[2-(5-methoxy-1H-indol-3-yl)ethyl]iodoacetamide (compound SD6, Figure five) was obtained by means of two routes as outlined by the synthetic pathway illustrated in Figure 5: Figure 5. Schematic representation on the synthesis of SD6.O NH2 O N H BrCOCH2Br K2CO3 AcOEt/H2O 5 ICH2COOH EDCI, HOBT, TEA, CH2Cl2 O N H H N Br O NaI, Acetone N H SD6 O H N I(A) by reaction of 5-methoxytryptamine with bromoacetyl bromide inside a biphasic medium (EtOAc-H2O) based on a variant of your Schotten aumann reaction (K2CO3) to receive a bromoacetyl derivative [18]. Substitution from the bromine atom of compound five by refluxing in acetone with sodium iodide resulted inside the iodo derivative SD6. (B) by a peptide-coupling reaction with iodoacetic acid within the presence of EDCI and HOBt in the presence of TEA in methylene chloride to generate the iodo derivative SD6.Fmoc-3VVD-OH Chemscene Int. J. Mol. Sci. 2013,3.8.two. Synthesis of N-[2-(5-methoxy-1H-indol-3-yl)ethyl]iodoacetamide (compound SD6, Figure 5), Route B Technique A: A option of three.PMID:25269910 11 g (0.01 mol) of compound 5 in 50 mL of anhydrous acetone was treated with 1.5 g (0.01 mol) of sodium iodide and also the mixture heated at reflux for two h. Immediately after cooling, the reaction mixture was filtered and evaporated. The residue was then crystallized from toluene, resulting in 2.five g (70 ) of compound 5. Approach B: A resolution of iodoacetic acid (1.85 g, 0.01 mol) in 50 mL of methylene chloride was stirred at -10 for 20 min. Triethylamine (1.62 mL, 0.012 mol), EDCI (1.86 g, 0.0012 mol), and HOBt (1.62 g, 0.0012 mol) have been added, and the mixture stirred at ?0 for 30 min. A answer of 5-methoxy tryptamine (1.9 g, 0.01 mol) in ten mL of methylene chloride was cooled at ?0 and added drop-wise. Right after 6 h of stirring at area temperature, the reaction mixture was washed with water, a 1M HCl solution, water, a 10 NaOH answer, and water until a pH of 7 was reached. The organic phase was dried more than MgSO4, filtered, and concentrated beneath decreased pressure. The residue was then crystallized from toluene, acquiring two.six g (73 ) of SD6. Mp 159 ; 1H NMR (80 MHz, CDCl3) eight.32 (br s, 1H), 7.32 (d, 1H, J = eight.2 Hz ), 6.96 (d, 1H, J = 2.5Hz), 7.02 (d, 1H, J = two.3 Hz), six.80 (dd, 1H, J = two.5 Hz and 8.2 Hz), 5.