Alternatived Products of [ 1067187-88-5 ]
Product Details of [ 1067187-88-5 ]
CAS No. : | 1067187-88-5 |
MDL No. : | MFCD18711520 |
Formula : |
C9H3F3INO2
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Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | - |
M.W : |
341.03
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Pubchem ID : | - |
Synonyms : |
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Safety of [ 1067187-88-5 ]
Signal Word: | |
Class: | |
Precautionary Statements: | |
UN#: | |
Hazard Statements: | |
Packing Group: | |
Application In Synthesis of [ 1067187-88-5 ]
* 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.
- Upstream synthesis route of [ 1067187-88-5 ]
- Downstream synthetic route of [ 1067187-88-5 ]
- 1
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[ 13061-96-6 ]
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[ 1067187-88-5 ]
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[ 1067187-89-6 ]
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[ 391-12-8 ]
Yield | Reaction Conditions | Operation in experiment |
|
With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In monoethylene glycol diethyl ether; water;Heating / reflux; |
The procedure described by Lisowski et al. (see J. Org. Chem., 2000, 65: 4193) was followed. Intermediate 79 (1.12 g, 3.28 mmol) and tetrakis(triphenylphosphine)palladium (190 mg, 0.16 mmol) were taken up in 100 mL of ethylene glycol dimethyl ether in a 500 mL round-bottom flask. This solution was purged three times by opening to vacuum followed by backfilling with nitrogen. Methylboronic acid (390 mg, 6.6 mmol) was added, followed by a solution of sodium bicarbonate (0.55 g, 6.6 mmol) in 100 mL of water, and the evacuation/nitrogen backfill procedure was repeated once more. The mixture was heated at reflux temperature and monitored for product appearance/starting material disappearance by LC-MS analysis. After 1.5 hours, an additional 190 mg (0.16 mmol) of the palladium catalyst was added and the reaction allowed to be heated at reflux temperature overnight. The organic solvent was removed and the remaining aqueous mixture was partitioned between 100 mL each of 2 M hydrochloric acid and ethyl acetate. The aqueous layer was extracted with additional ethyl acetate and the combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated to give the crude product, which was purified by flash chromatography over silica gel (0-6% ethyl acetate in dichloromethane) to give intermediate 80 of sufficient purity (the product contained about 20% of the deiodinated side-product, 7-(trifluoromethyl)isatin). 1H NMR (400 MHz, DMSO-d6) delta 3.33 (s, 3H), 7.62 (s, 1H), 7.68 (s, 1H), 11.35 (s, 1H). |
- 2
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[ 391-12-8 ]
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[ 1067187-88-5 ]
Yield | Reaction Conditions | Operation in experiment |
87% |
With bis(pyridine)iodonium (I) tetrafluoroborate; trifluorormethanesulfonic acid; In dichloromethane; at 20℃; for 0.666667h; |
The iodination methodology described by C. Lamas, J. Barluenga et al. (see J. Org. Chem., 1996, 61: 5804) was followed. Intermediate 6 (8.79 g, 40.9 mmol) was taken up in 105 mL of anhydrous dichloromethane in a 500 mL round-bottom flask. Bis(pyridine)iodonium(I) tetrafluoroborate (23 g, 61 mmol) was added, followed by trifluoromethanesulfonic acid (10.8 mL, 18.4 g, 0.123 mol). The mixture was stirred at room temperature for 40 minutes, until LC-MS analysis showed complete disappearance of starting material. The solution was treated with 105 mL of water and extracted with two 45 mL-portions of dichloromethane. The combined organic layers were washed with 5percent aqueous sodium thiosulfate, dried over anhydrous magnesium sulfate, filtered, and concentrated to give pure product (intermediate 79, 12.0 g, 87percent yield). 1H NMR (400 MHz, DMSO-d6) delta 8.03 (s, 1H), 8.11 (s, 1H), 11.55 (s, 1H). |