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CAS No. : | 1011-65-0 | MDL No. : | MFCD00153023 |
Formula : | C10H9NO2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | DRYBMFJLYYEOBZ-UHFFFAOYSA-N |
M.W : | 175.18 | Pubchem ID : | 2737635 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | Preparation of 1-Methyl-5- [5- (2-phenoxy-ethylsulfanylmethyl)- [1, 3,4] oxadiazol-2-yl]- 1H-indole a) 1-Methyl-lH-indole-5-carboxylic acid methyl ester A DMF solution of methyl indole-5-carboxylate (5.0 g, 28.54 mmol, 1 eq. ) was cooled in an ice bath and then treated with sodium hydride (1.37 g, 34.29 mmol, 1.2 eq. ). After 20 minutes at 0C, the reaction was treated with iodomethane (6.08 g, 2.7 mL, 42. 81 mmol, 1.5 eq. ). After stirring for 4 hours, the reaction was quenched with water. The reaction was extracted twice with 150 mL of ethyl acetate and the organic layers were combined, dried, filtered, and the solvent removed in vacuo leaving a yellow oil that was triturated with hexane to obtain 1-methyl-lH-indole-5-carboxylic acid methyl ester (5.22 g, 97% yield) as a tan solid. | |
76% | Preparation of methyl 1-methyl-1 f-indoie-5-cari30xylate To a suspension of aH (264 mg, 1.1 mmoi) in DMF (20 ml) was added methyl 1H-indoie-5-carboxylate (1.05 g, 6 mmoi) at 0 QC and the resulting mixture was stirred for 20 minutes, Mel (1.70 g, 2,2 mmo) was added to the reaction mixture, which was then allowed to warm to 50 C overnight. The reaction liquid was partitioned between EtOAc and water. The organic layer was washed with water and brine, dried over Na2S04 and concentrated to give the crude product, which was purified by silica gel column (EtQAc/petroleum ether - 1/10) to give the target compound (860 mg, 76%). LCMS: m/z 190.1 [M+Hf, | |
56% | With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20℃; for 8h; | 1H-indole-6-carboxylic acid methyl ester (1.0g, 5.71mmol) was dissolved in dimethylformamide (10ml), and methyl iodide (0.53ml, 8.56mmol) and sodium hydride (374mg, 8.56mmol) were added dropwise thereto at 0. The mixture was stirred for 8 hours at room temperature. 1N hydrochloric acid solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and filtered. Filtrate was distilled under reduced pressure and separated by column chromatography to obtain the title compound (600mg, 56%). |
Sodium hydride (1.71 g, 42.80 mmol, 60% in mineral oil) was added at 0 C. in portions to a stirred solution of methyl indole-5-carboxylate (5.0 g, 28.53 mmol, CASRN 1670-81-1) in DMF over a 30 min period. While still at 0 C. MeI (5.33 mL, 85.61 mmol) was added. The resulting mixture was stirred at 0 C. for 60 min then at RT overnight. The mixture was partitioned between H2O and EtOAc and the aqueous layer was further extracted with EtOAc. The combined organic extracts were washed with water, dried (MgSO4), filtered and concentrated to afford 4.91 g of 1-methyl-1H-indole-5-carboxylic acid methyl ester (53). | ||
With potassium hydride; In tetrahydrofuran; at 20℃; for 0.5h; | Step A. 1-Methyl-indole-5-carboxylic acid methyl ester. Under an atmosphere of nitrogen, a solution of indole-5-carboxylic acid methyl ester (2.5 g, 14.3 mmol) in dry tetrahydrofuran (20 mL) was added dropwise to a stirred slurry of hexane-washed potassium hydride (1.63 g, 14.3 mmol, 35% in oil). When the hydrogen evolution ceased, iodomethane (1.3 mL, 21.5 mmol) was added to the stirred solution. After an additional 30 minutes at room temperature, the precipitate was filtered and washed with diethyl ether. The filtrate was concentrated in vacuo and the residue triturated with hexane to provide the title compound as a yellow solid (2.6 g). | |
With sodium hydride; In dimethyl sulfoxide; at 0℃; for 2h; | TE4O was synthesized by the reaction scheme:Methyl 1-methyl-1H-indole-5-carboxylate was prepared according to the article, Org. Lett. 2014, 16, 1124-1127, which is hereby incorporated by reference in its entirety. Rf = 0.49 in hexanes: EtOAc = 2:1. ?HNIVIR (400 MHz, CDC13) ppm 8.4 (s, 1H) 7.9 (d, J 8.6 Hz, 1H) 7.3 (d, J= 9.4 Hz, 1H) 7.1 (d, J= 3.1 Hz, 1H) 6.6 (d, J= 3.9 Hz, 1H) 3.9 (s, 3H)3.8 (s, 3H). ?3C NMR (101 IVIHz, CDC13) ppm 168.2, 139.0, 130.2, 127.9, 123.9, 122.8,121.3, 108.8, 102.6, 51.7, 32.9. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; | Step A. 1-Methyl-indole-5-carboxylic Acid Methyl Ester Under an atmosphere of nitrogen, a solution of indole-5-carboxylic acid methyl ester (2.5 g, 14.3 mmol) in dry tetrahydrofuran (20 mL) was added dropwise to a stirred slurry of hexane-washed potassium hydride (1.63 g, 14.3 mmol, 35% in oil). When the hydrogen evolution ceased, iodomethane (1.3 mL, 21.5 mmol) was added to the stirred solution. After an additional 30 minutes at room temperature, the precipitate was filtered and washed with diethyl ether. The filtrate was concentrated in vacuo and the residue triturated with hexane to provide the title compound as a yellow solid (2.6 g). NMR (CDCl3, 400 MHz): delta 3.82 (s, 3H), 3.93 (s, 3H), 6.58 (dd, 1H), 7.10 (d, 1H), 7.32 (d, 1H), 7.92 (dd, 1H), 8.39 (s, 1H); MS (El, m/z): 189 [M]+, 158, 130. | |
In tetrahydrofuran; | Step A. 1-Methyl-indole-5-carboxylic acid methyl ester Under an atmosphere of nitrogen, a solution of indole-5-carboxylic acid methyl ester (2.5 g, 14.3 mmol) in dry tetrahydrofuran (20 mL) was added dropwise to a stirred slurry of hexane-washed potassium hydride (1.63 g, 14.3 mmol, 35% in oil). When the hydrogen evolution ceased, iodomethane (1.3 mL, 21.5 mmol) was added to the stirred solution. After an additional 30 minutes at room temperature, the precipitate was filtered and washed with diethyl ether. The filtrate was concentrated in vacuo and the residue triturated with hexane to provide the title compound as a yellow solid (2.6 g). NMR (CDCl3, 400 MHz): delta 3.82 (s, 3H), 3.93 (s, 3H), 6.58 (dd, 1H), 7.10 (d, 1H), 7.32 (d, 1H), 7.92 (dd, 1H), 8.39 (s, 1H) MS (EI, m/z): 189 [M]+, 158, 130 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 200℃; for 2h;Microwave irradiaition; | A mixture of Ij (1.14 mmol, 200 mg), laa (1.14 mmol, 150 mg), K2CO3 (2.28 mmol, 315 mg) and NMP (1.5 mL) was heated at 200 0C in a microwave reactor for 2 h. The mixture was poured into water (50 mL) and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under vacuo. Purification was carried by flash column chromatography (silica gel, 15percent EtO Ac/heptane) to give 290 mg of lbb (290 mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | To a solution of oxalyl chloride (2.08 g, 16.4 mmol) in dry toluene (10 mL) was added dropwise at 0 C a solution of <strong>[29006-02-8]4-methoxybutyric acid</strong> (1.76 g, 14.9 mmol) in dry toluene (10 mL). After stirring the mixture at room temperature over night, the solvent was distilled off. The residue was dissolved in dry CH2Cl2 (30 mL) and treated with methyl indole-5-carboxylate (801 mg, 4.57 mmol) at room temperature. Then AlCl3 (1.72 g, 12.9 mmol) was added at 0 C and the mixture was stirred at this temperature for 15 min. After addition of water, the reaction mixture was exhaustively extracted with ethyl acetate. The combined organic layers were dried (Na2SO4) and concentrated. Recrystallization from ethyl acetate gave the pure product (588 mg, 47%). C15H17NO4 (275.3); mp 167-168 C; 1H NMR (DMSO-d6): delta (ppm) 1.83-1.90 (m, 2H), 2.90 (t, 2H, J = 7.3 Hz), 3.21 (s, 3H), 3.37 (t, 2H, J = 6.5 Hz), 3.85 (s, 3H), 7.53 (d, 1H, J = 8.6 Hz), 7.82 (dd, 1H, J = 8.6 Hz and 1.7 Hz), 8.44 (s, 1H), 8.87-8.88 (m, 1H), 12.22 (sbroad, 1H); MS (EI): m/z (%) 275 (4) [M]+, 217 (100). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With oxygen; copper(II) bis(trifluoromethanesulfonate); cobalt(II) chloride; In ethanol; at 40℃; under 760.051 Torr; for 48h;Sealed tube; | Add 2-methyl carboxylate to phenol (0.2 mmol, 1.0 equiv.), 5-methyl carboxylate indole (0.2 mmol, 1.0 equiv.), and CoCl2 (1.3 mg, 5 mol%) in a 25ml sample bottle. , Cu(OTf)2 (7.3mg, 10mol%) and magnets, sealed with a rubber stopper, vacuumed and then filled with O2, transferred 4ml of 95% ethanol with a syringe to a sealed sample bottle, and then put the bottle inside The atmosphere was communicated with 1atm O2. After the reaction was stirred at 40C for 48h, the solvent was removed by blowing air at a constant temperature of 30C for 1 hour. The residue was purified by column chromatography on silica gel. The eluent was petroleum ether/ethyl acetate 20: 1 to 5:1 gradient elution. The target product was collected, and the isolated yield was 60% |
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