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CAS No. : | 675109-30-5 | MDL No. : | MFCD13177830 |
Formula : | C8H6INO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HWGBKJIBYIUGNE-UHFFFAOYSA-N |
M.W : | 259.04 | Pubchem ID : | 22220918 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P280 | UN#: | |
Hazard Statements: | H302-H317 | 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 |
---|---|---|
With potassium phosphate; copper(l) iodide; 8-quinolinol; In N,N-dimethyl-formamide; at 130℃; for 0.5h;Microwave irradiation; Inert atmosphere; Sealed tube; | [0348] Into a 20-mL microwave tube were added Example 15a (500 mg, 1.93 mmol), Example 15b (229 mg, 2.12 mmol), Cul (184 mg, 0.97 mmol), K3PO4 (819 mg, 3.86 mmol) and quinolin-8-ol (50 mg, 0.38 mmol) successively. Then, DMF (6 mL) was added by a syringe. The mixture was degassed by nitrogen for three times and sealed. The reaction was heated to 130°C under microwave for 30 min. The reaction was filtered, washed by MeOH and purified by Prep-HPLC (by Ultimate XB-C18, 50 x 250 mm, 10 m, speed: 80 mL/min, eluent: H20/CH3CN = from 80/20 to 20/80 over 50 min) to afford a mixture of Example 15c&15d (80 mg, yield 17 percent) as a white solid. LCMS [M+l] + = 240.0 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2% | With potassium phosphate; copper(l) iodide; 8-quinolinol; In N,N-dimethyl-formamide; at 130℃; for 1h;Microwave irradiation; | [0428] To a solution of Example 62g (600 mg, 2.317 mmol) in DMF (10 mL) was added Example 62h (275 mg, 2.548 mmol), Cul (221 mg, 1.16mmol), K3P04 (981 mg,4.63 mmol) andquinolin-8-ol (67 mg, 0.463mmol). The mixture was stirred at 130°C for lh in microwave. The suspension was filtered and the liquid was purified byPrep-HPLC (by Ultimate XB-C18, 50 x 250 mm, 10 mupiiota, speed: 80 mL/min, eluent: H20/CH3CN = from 80/20 to 20/80 over 50 min)to afford Example 62i (30 mg, yield: 2percent) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7%; 14% | [0349] To a solution of Example 15c&15d (70 mg, 0.29 mmol) in 1,4-dioxane (2 mL) was added Example 15e (101 mg, 0.32 mmol), Cul (22 mg, 0.12 mmol), K3PO4 (125 mg, 0.59 mmol) and N1.N2- dimethylcyclohexane-l,2-diamine (17 mg, 0.12 mmol) successively. The mixture was degassed by nitrogen for three times and heated at 100°C for 16 h. The reaction was filtered and purified by silica gel chromatography to give a crude product, which was further purified by Prep-HPLC (by Ultimate XB- C18, 50 x 250 mm, 10 m, speed: 80 mL/min, eluent: H20/CH3CN = from 80/20 to 20/80 over 50 min) to afford the desired product Example 15 (17 mg, yield 14 percent) & the other isomer Example 16 (7 mg, yield 7percent) as a white solid. LCMS [M/2+l]+ = 213.6 Example 15 [0350] 1H NMR (400 MHz, DMSO-d6) 6 8.92 (s, 1H), 8.63 (d, J= 8.3 Hz, 1H), 8.26 (d, J= 1.5 Hz, 1H), 8.08 (t, J= 8.0 Hz, 1H), 8.03 (d, J= 2.2 Hz, 1H), 7.97 (dd, J= 8.2, 2.2 Hz, 1H), 7.91 (d, J= 7.6 Hz, 1H), 7.84 (d, J = 8.2 Hz, 1H), 7.65 (d, J= 1.5 Hz, 1H), 5.54-5.46 (m, 1H), 5.17 (s, 2H), 1.82 (td, J= 8.4, 4.3 Hz, 1H), 1.56 (d, J= 6.7 Hz, 6H), 0.79 (dd, J= 8.4, 2.5 Hz, 2H), 0.69 (dd, J = 5.1, 2.3 Hz, 2H). Example 16 [0351] 1H NMR (400 MHz, DMSO-< delta 8.92 (s, 1H), 8.65-8.60 (m, 1H), 8.26 (s, 1H), 8.08 (t, J= 8.0 Hz, 1H), 8.04 (d, J= 2.1Hz, 1H), 7.97 (dd, J= 8.2, 2.2 Hz, 1H), 7.91 (dd, J= 7.6, 0.9 Hz, 1H), 7.84 (d, J = 8.2 Hz, 1H), 7.66 (s, 1H), 5.50 (p, J= 6.7 Hz, 1H), 5.17 (s, 2H), 1.83 (td, J= 8.4, 4.3 Hz, 1H), 1.56 (d, J= 6.7 Hz, 6H), 0.83-0.78 (m, 2H), 0.70 (dt, J= 5.1, 2.8 Hz, 2H). |