Substituted indolealkanoic acids
a technology of indolealkanoic acid and substituted indolealkanoic acid, which is applied in the direction of biocide, drug composition, metabolic disorder, etc., can solve the problem that no human clinical trial has demonstrated sufficient efficacy without significant undesirable side effects
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example 2
[0141] 22
[0142] 5chloroindole-3-acetonitrile
[0143] A solution of aqueous formaldehyde (37%, 2.95 mL, 66.0 mmol) and dimethylamine (40%, 5.30 mL, 66.0 mmol) in 20 mL EtOH was cooled to 0.degree. C. 5-Chloroindole (4.0 g, 26.4 mmol) was dissolved in a HOAc:EtOH mixture (1:1, 40 mL) and added dropwise to the reaction mixture. After stirring at this temperature for 2 h, the mixture was allowed to warm to room temperature and stir overnight. The mixture was added to a sat'd solution of NaHCO.sub.3. 1 N NaOH was added until the pH was between 9-10. The resulting mixture was extracted with CH.sub.2Cl.sub.2 (3.times.). The organics were combined and washed with a sat'd aq. NaCl, dried over MgSO.sub.4, filtered and concentrated in vacuo to give 4.65 g (85%) of 5-chloro-3-[(dimethylamino)methyl] indole as a yellow powder. Without further purification, 5-chloro-3-[(dimethylamino)m-ethyl] indole (4.65 g, 22.4 mmol) was dissolved in dimethylformamide (80 mL) at room temperature with stirring. To...
example 3
[0146] 23
[0147] 2,3,5,6-Tetrafluoroacetanilide
[0148] A solution of 2,3,5,6-tetrofluoroaniline (200 g, 1.21 mol) in anhydrous pyridine (103 mL, 1.27 mol) was treated with acetic anhydride (120 mL, 1.27 mol) and heated to 120.degree. C. for 2 h. After cooling to room temperature, the solution was poured into ice-cold water (500 mL). The resulting precipitate was filtered, dissolved in ethyl acetate, dried over MgSO.sub.4, filtered and concentrated. The solid material was washed with heptane (200 mL) and dried to give 2,3,5,6-tetrafluoroacetanilide as a white crystalline solid (206 g, 82%): mp 136-137.degree. C.; R.sub.f 0.48 (50% ethyl acetate in heptane); .sup.1H NMR (DMSO -d.sub.6, 300 MHz) .delta.10.10 (s, 1 H), 7.87-7.74 (m, 1 H), 2.09 (s, 3 H). Anal. Calcd for C.sub.8H.sub.5F.sub.4NO: C, 46.39; H, 2.43; N, 6.67. Found C, 46.35; H, 2.39; N, 6.68.
[0149] 2,3,5,6-Tetrafluorothioacetanilide
[0150] A flame-dried, 4-necked 5,000 mL round-bottomed flask was charged with phosphorous pentas...
example 4
[0161] 24
[0162] 5-Methyl-3-(4,5,7-trifluorobenzothiazol-2-yl)methyl-indole-N-acetic Acid was prepared in a manner analogous to that set forth in Example 2, except 5-methylindole was used instead of 5-chloroindole in step 1: mp 131-133.degree. C.; .sup.1H NMR (DMSO-d.sub.6, 300 MHz) .delta. 7.73-7.62 (m, 1 H), 7.39 (s, 1 H), 7.30 (s, 1 H), 7.27 (d, J=9.0 Hz, 1 H), 6.96 (dd, J.sub.1=9.0 Hz, J.sub.2=2.4 Hz, 1 H), 4.98 (s, 2 H), 4.60 (s, 2 H), 2.32 (s, 3 H); LRMS calcd for C.sub.19H.sub.13F.sub.3N.sub.2O.sub.2S: 390.0; found 391.0 (M+1).sup.+. Anal. Calcd for C.sub.19H.sub.13F.sub.3N.-sub.2O.sub.2S: C, 58.46; H, 3.36; N, 7.18; S, 8.21. Found: C, 58.36; H, 3.30, N, 7.10, S, 8.20.
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