1953-54-4, 5-Hydroxyindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
l-(2-Chloroquinolin-6-yl)ethanone (lOOmg, 0.486 mmol) and 5-hydroxyindole (65 mg, 0.486 mmol), copper iodide (93 mg, 0.486 mmol) and cesium carbonate (475.3 mg, 1.46 mmol) were taken into DMF (8 ml) and heated in a microwave reactor at 15O0C for 50 min. The reaction was cooled to room temperature and water added to the reaction mass. The undissolved solids were filtered through celite and the filtrate was extracted with EtOAc twice. The organic extracts were washed with cold water and brine solution. The organic extracts were dried over sodium sulfate and concentrated under reduced pressure under vacuum. Purification of the residue by column chromatography (EtOAc:hexane 2:8) afforded 130 mg (88.4%) of l-[2-(lH-indol-5-yloxy)quinolin-6-yl]ethanone. LCMS [M+H] 303.5; 1H-NMR (400 MHz, CDCl3) delta 8.375-8.379 (d, IH, J=I .6 Hz), 8.27 (bs, IH), 8.17-8.19 (d, IH, J=8.8Hz), 8.13-8.16 (dd, IH, J=10.8 Hz, 6.8 Hz), 7.79-7.82 (d, IH, J=8.8 Hz), 7.49 -7.50 (d, IH, J=2Hz), 7.42-7.45 (d, IH, J=8.8 Hz), 7.27-7.28 (t, IH, 2.8 Hz), 7.12-7.14 (d, IH, J=8.8 Hz), 7.07-7.1 (dd, IH, J=I 1.2, 6.4 Hz), 6.57 (bs, IH), 2.69 (s, 3H) ppm. To a chilled solution of l-[2-(lH-indol-5-yloxy)quinolin-6-yl]ethanone (130 mg, 0.43 mmol) in DCM (10 ml) was added 4-(dimethylamino)pyridine (52.5 mg, 0.43 mmol). The mixture was stirred at O0C for 10 min after which di-t-butyl carbonate (0.158 ml, 0.86 mmol) was added. The reaction mixture was stirred for 30 min at ambient temperature. The reaction mixture was diluted with DCM and washed with water and brine before drying over sodium sulfate. The organic layer was evaporated under vacuum. Purification of the residue by column chromatography (EtOAc:hexane 2:8) afforded 140 mg (80.9%) yield of 5-(6-acetylquinolin-2-yloxy)indole-l-carboxylic acid tert-butyl ester. LCMS [M+H] 403.51; 1H-NMR (400 MHz, CDCl3) delta 8.382-8.386 (d, IH, J=I .6 Hz), 8.19-8.21 (d, 2H, J=8.8 Hz), 8.13-8.16 (dd, IH, J=10.8, 6.8 Hz), 7.77-7.79 (d, IH, J=9.2 Hz), 7.65-7.66 (d, IH, J=3.6 Hz), 7.430 -7.436 (d, IH, J=2.4 Hz), 7.18-7.20 (dd, IH, J=10.8, 6.8 Hz), 7.15-7.17 (d, IH, J=8.8 Hz), 6.57-6.58 (d, IH, J=3.6 Hz), 2.70 (s, 3H), 1.69 (s, 9H) ppm. 5-(6-Acetylquinolin-2-yloxy)indole-l-carboxylic acid t-butyl ester (140 mg, 0.348 mmol), ammonium acetate (322 mg, 4.175 mmol) and molecular sieves powder 4A (Ig) were taken into methanol (25ml) and stirred at room temperature for 20 min after which sodium cyanoborohydride (33 mg, 0.522 mmol) was added. The reaction mixture was refluxed overnight. The reaction mixture was cooled to room temperature and filtered through celite. The solvent was evaporated under vacuum to obtain crude which was dissolved in water and extracted with EtOAc. The EtOAc layer was washed with brine and dried over sodium sulfate. The organic layer was evaporated to obtain crude which was taken into the next step without further purification.
1953-54-4 5-Hydroxyindole 16054, aindole-building-block compound, is more and more widely used in various.
Reference£º
Patent; FOREST LABORATORIES HOLDINGS LIMITED; SARMA, Pakala Kumara, Savithru; ACHARYA, Vinod, Parameshwaran; KASIBHATLA, Srinivas, Rao; TIWARI, Atul; REDDY, Vantaddu, Nagarjuna; BISCHOFF, Alexander; WO2010/127208; (2010); 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