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To a stirred solution of methyl 1 H-indole-6-carboxylate (0.76g, 4.34mmol) in DMF (10ml) at room temperature was added sodium hydride (0.35g, 8.75mmol). The resultant suspension was stirred for 30min at room temperature followed by the addition of methyl iodide (0.54ml, 8.67mmol). The reaction mixture was stirred for 2Oh at room temperature and was then quenched by the addition of water (20ml) and ethyl acetate (20ml). The aqueous layer was extracted with ethyl acetate (3 x 30ml) and the combined extracts were dried with a phase separating column. The solvent was then removed in vacuo to give the desired product as an off-white solid (0.85g, 100%). LC-MS (Acidic) (MH+=I 90). The product was used without further purification
100%
Method D; 1 -methyl-1 /-/-<strong>[50820-65-0]indole-6-carboxylic acid methyl ester</strong> (Intermediate compound); A mixture of methyl-indole-6-caroxylate (3.0 g, 16.6 mmol), sodium hydride (1.0 g, 24.9 mmol), DMF (20 ml) was stirred for 1 h at room-temperature followed by addition of iodomethane (4.7 g, 33.2 mmol) and stirring at room- temperature for 15 h. The mixture was extracted with chloroform and evaporated. The product was isolated by evaporation. Yield 3.2 g (100%).
In N-methyl-acetamide;
i 1-methyl<strong>[50820-65-0]indole-6-carboxylic acid methyl ester</strong> To a stirred solution of methyl 6-indolecarboxylate (5 g) in dry dimethylformamide (30 ml) cooled to 5 C., sodium hydride (60% dispersion in oil, 1.49 g) was added portionwise. The reaction mixture was stirred at 5 C. for 0.5 hour, then a solution of methyliodide (12.18 g) in dry dimethylformamide (10 ml) was added dropwise. After 2 hours, the reaction mixture was diluted with water and the product obtained, after cooling and filtration.
1.16 g
With potassium hydroxide; In dimethyl sulfoxide; at 20℃; for 1h;
Method 3 Synthesis of methyl 1-methylindole-6-carboxylate (Intermediate 4) To a solution of R-3 (1 g, 5.7 mmol) in DMSO (10 mL) is added KOH (800 mg, 14.3 mmol) and iodomethane (0.534 mL, 8.6 mmol). After stirring at room temperature for 1 h the reaction mixture is diluted with water (50 mL) and the resultant suspension filtered and washed with more water. The solid is dried in vacuo to give the title intermediate I-4 (1.16 g) m/z 190.0 [M+H].
With sodium hydroxide; In N-methyl-acetamide;
REFERENCE EXAMPLE 5 Preparation of methyl 1-methyl-6-indolecarboxylate The reaction was carried out in a manner similar to Reference Example 4 except for using 3.00 (17.1 mmol) of methyl 6-indolecarboxylate, 0.68 g (17.1 mmol) of 60% sodium hydroxide, 4.86 g (34.4 mmol) of methyl iodide and 60 ml of dimethylformamide. Thus 2.75 g (86.9%) of methyl 1-methyl-6-indolecarboxylate was obtained. 1H NMR (CDCl3) δ: 3.86 (3H, s), 3.95 (3H, s), 6.51-6.53 (1H, m), 7.21 (1H, d, J=3.3 Hz), 7.63 (1H, d, J=8.6 Hz), 7.78-7.82 (1H, m), 8.10 (1H, S).
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