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CAS No. : | 53462-88-7 | MDL No. : | MFCD06656838 |
Formula : | C11H9NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HWQJAOMFBDZMPB-UHFFFAOYSA-N |
M.W : | 203.19 | Pubchem ID : | 12396096 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | Packing Group: | N/A |
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 |
---|---|---|
95% | Stage #1: With oxalyl dichloride In dichloromethane at 0℃; for 0.5 h; Inert atmosphere Stage #2: at 20℃; for 1 h; |
2M solution of oxalyl dichloride in dichloromethane (DCM) (1.712 ml, 3.425 mmol) was added to DCM (15 mL) cooled down in an ice-water bath. N,N-dimethylformamide (0.250 g, 3.425 mmol) was added dropwise under nitrogen. The reaction mixture was stirred at 0°C for 30 mm. Then methyl 1H-indole-4-carboxylate (0.5 g, 2.854 mmol) in DCM (10 mL) was added. The reaction mixture was warmed to room temperature and stirred for 1 h. The solvent was removed. THF (15 mL) and 20percent aqueous ammonium acetate were added. The reaction mixture was stirred under reflux (—70 °C) for 30mm. The reaction mixture was then extracted with ethyl acetate. The combined organics (organic phases) were concentrated; the residue was purified by silica gel column chromatography with 90percent ethyl acetate/hexanes to give the title compound (551 mg, 95.0 percent) as white solid. LCMS m/z = 204.2 [M+Hj ‘H NMR (400 MHz, CDC13) ö ppm 4.00 (s, 3H), 7.34 (t, J = 7.8 Hz, 1H), 7.63 (dd, J = 8.0 and 1.0 Hz, 1H), 7.87 (dd, J= 7.5 and 1.0 Hz, 1H), 8.10 (d, J= 3.2 Hz, 1H), 9.08 (br s, 1H), 10.53 (s, 1H). |
81.6% | With trichlorophosphate In N,N-dimethyl-formamide at 0 - 35℃; for 1.33 h; | The reaction flask was charged with 44 mL of DMF, cooled in an ice bath to 0 ° C, and 6.3 mL of phosphorus oxychloride (P0C13) was slowly added dropwise,The temperature below 10 ° C, drop complete, continue stirring 20min.At 10 ° C with(63 mmol) of indole-4-carboxylic acid methyl ester in 19 mL of DMF was added dropwise at 35 ° C for lh. After cooling, 38 mL of water was added and the pH was adjusted to 9 to 15 with 15percent sodium hydroxide solution. 10. The reaction was poured into ice water, stirred, precipitated solid, filtered and dried to give 10.5 g of yellow green solid in 81.6percent yield. |
60% | at 0 - 20℃; for 1 h; Inert atmosphere | Intermediate compound 11: Synthesis of methyl 3-formyl-1H-indole-4- carboxylateTo a stirred solution of 573 mg (3.27 mmol) of methyl 1 H-indole-4-carboxylate in 6 mL of anhydrous DMF under dry argon atmosphere, 0.9 mL (9.8 mmol) of phosphorus chloride oxide was added at 0 5C and the resulting mixture was stirred at room temperature for 1 h. Then, the reaction mixture was poured into cold saturated NaH2C03 aqueous solution and stirred for 30 min. The resultant mixture was extracted with EtAcO (x3). The combined organic layer was dried over anhydrous Na2S04 and filtered. Then, the filtrate was condensed under reduced pressure and purified by silica gel flash column chromatography to provide methyl 3- formyl-1 H-indole-4-carboxylate as a white solid (400 mg, 60percent).1 H NMR (300 MHz, Chloroform-d) ? 10.49 (s, 1 H), 9.93 (br s, 1 H, NH), 8.05 (d, J = 3.3 Hz, 1 H), 7.83 (dd, J = 7.5, 1 .0 Hz, 1 H), 7.64 (dd, J = 8.2, 1 .0 Hz, 1 H), 7.31 (t, J = 7.9 Hz, 1 H), 4.00 (s, 3H). |
551 mg | Stage #1: With oxalyl dichloride In dichloromethane at 0℃; for 0.5 h; Inert atmosphere Stage #2: at 0 - 20℃; for 1 h; Inert atmosphere |
A 2M solution of oxalyl dichloride in DCM (1.712 mL, 3.425 mmol) was added to DCM (15 mL) in an ice-water bath. /V,/V-dimethylformamide (0.250 g, 3.425 mmol) was added dropwise under nitrogen. The reaction was stirred for 30 minutes at 0 °C. Then methyl lH-indole-4-carboxylate (0.5 g, 2.854 mmol) in DCM (10 mL) was added. The reaction was warmed to room temperature and stirred for 1 hour. The solvent was removed. THF (15 mL) and 20percent aqueous ammonium acetate were added. The reaction was stirred for 30 minutes under reflux (-70 °C). The mixture was then extracted with ethyl acetate. The combined organic fractions were concentrated. The residue was purified by silica gel column chromatography to give the title compound (551 mg) as a white solid. LCMS m/z = 204.2 [M+H]+; NMR (400 MHz, CDC13) δ 4.00 (s, 3H), 7.34 (t, 7 = 7.8 Hz, 1H), 7.63 (dd, 7 = 8.0 and 1.0 Hz, 1H), 7.87 (dd, 7 = 7.5 and 1.0 Hz, 1H), 8.10 (d, 7 = 3.2 Hz, 1H), 9.08 (bs, 1H), 10.53 (s, 1H). |
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