289483-87-0, 7-Amino-4-methyl-1H-indole-3-carbonitrile is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
Crystals of the title compound were synthesized using the same reaction conditions and recrystallization conditions as for the N-(3-cyano-4-methyl-1H-indol-7-yl)-3-cyanobenzenesulfonamide described in WO00/50359. To a solution of 7-amino-3-cyano-4-methyl-1H-indole (10 g, 58.4 mmol) in tetrahydrofuran (200 ml) were added pyridine (20 ml) and 3-cyanobenzenesulfonyl chloride (12.5 g), followed by stirring at room temperature for 3.5 hours. After further adding 2N hydrochloric acid (100 ml), extraction was performed with ethyl acetate. The organic layer was washed with water (twice) and brine in that order, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate = 2:1-3:2). A mixed solvent of ethanol-hexane (1:2) was added thereto, and after sonication, the precipitate was collected by filtration and washed with a mixed solvent of ethanol-hexane (1:3). The mixture was dried overnight under reduced pressure to give the title compound (9.33 g, 27.7 mmol, 47% yield). 1H-NMR spectrum (DMSO-d6) delta (ppm): 2.58 (3H, s), 6.52 (1H, d, J=7.6Hz), 6.80 (1H, d, J=7.6Hz), 7.74 (1H, m), 7.92 (1H, d, J=8.0Hz), 8.12 (2H, m), 8.19 (1H, d, J=3.2Hz), 10.13 (1H, s), 12.03 (1H, s). A powder X-ray diffraction pattern for the obtained crystals is shown in Fig. 2, and the diffraction angle (2theta) peak and peak intensity are shown in Table 6. [Table 6] PEAK No. 2 theta HALF WIDTH d-VALUE INTENSITY RELATIVE INTENSITY 1 5.960 0.235 14.8167 3492 49 2 8.100 0.212 10.9063 2820 40 3 8.440 0.188 10.4677 1968 28 4 11.920. 0.259 7.4184 4067 57 5 14.120 0.282 6.2671 7103 100 6 15.120 0.259 5.8548 2142 30 7 16.400 0.165 5.4006 2330 33 8 17.660 0.141 5.0180 1905 27 9 17.960 0.212 4.9349 1998 28 10 19.240 0.306 4.6093 5707 80 11 21.380 0.235 4.1526 2443 34 12 21.940 0.282 4.0478 5502 77 13 23.020 0.212 3.8603 2602 37 14 23.580 0.165 3.7699 3172 45 15 23.900 0.400 3.7201 3958 56 16 24.540 0.282 3.6245 2812 40 17 25.840 0.165 3.4451 4302 61 18 26.520 0.212 3.3582 3045 43 19 27.540 0.376 3.2361 3265 46 20 28.380 0.118 3.1422 2655 37 21 28.520 0.188 3.1271 2435 34 It was attempted to produce identical crystals by the same process as Example 1B, but the powder X-ray diffraction pattern did not match. In other words, the crystals obtained in Example 1B were presumably not of a single crystal form but were a mixture of multiple crystal forms. Moreover, it is believed that a single crystal form cannot be produced by the process of Example 1B.
As the paragraph descriping shows that 289483-87-0 is playing an increasingly important role.
Reference£º
Patent; Eisai Co., Ltd.; EP1666463; (2006); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles