Structure of 450-90-8
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 450-90-8 |
Formula : | C7H6FIO |
M.W : | 252.03 |
SMILES Code : | COC1=CC(F)=CC=C1I |
MDL No. : | MFCD18396916 |
InChI Key : | MBHUTPUUHOAWCJ-UHFFFAOYSA-N |
Pubchem ID : | 56965572 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 |
* 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 |
---|---|---|
78% | 4-Fluoro-2-methoxyaniline (2.50 g, 17.5 mmol) was dissolved in 14 mL of concentrated HCl, cooled to 0C, solution of NaNO2 (1.45 g, 21.0 mmol) in 13 mL of water was then added under stirring. It was stirred for 40 minutes, resulting solution was added dropwise at room temperature to a solution of KI (8.73 g, 52.6 mmol) in 30 mL of water. Resulting mixture was stirred at 35-40C for 1 hour, product was then extracted with ethyl acetate (3x70 mL), extract was washed with Na2S2O3 solution, dried with Na2SO4. Product was isolated by column chromatography on silica gel using hexane as eluent. Yield of 2-iodo-5-fluoroanysol 5 was 3.46 g (78%) obtained as colourless solid mass. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With isopropylmagnesium bromide; In tetrahydrofuran; at 20℃; for 19h;Inert atmosphere; Cooling with ice; | Add dry THF (30mL) to the reaction flask,Then add SM 69 (2.5g, 10mmol), Under nitrogen protection, add 1N isopropyl magnesium bromide (10mL, 1M in THF) under ice-water bath conditions,Then react at room temperature for 7 hours, and finally add tert-butyl 5-oxopyrrolidine-1-carboxylate (1.85g, 10mmol),Then react at room temperature for 12 hours. The reaction solution was poured into saturated aqueous ammonium chloride solution, extracted with 30 mL (10 mL×3) ethyl acetate, and the organic phases were combined.After drying with anhydrous sodium sulfate and purifying by column chromatography, Int 340-1 (1.7 g, 5.6 mmol) was obtained with a yield of 56%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With isopropylmagnesium bromide; In tetrahydrofuran; hexane; at 20℃; for 19h;Inert atmosphere; | Add dry THF (20mL) to a reaction flask containing SM 69 (2.52g, 10mmol), under nitrogen protection, and add isopropyl magnesium bromide (10mL, 1M in Hexane) to the flask under ice-water bath conditions,Then remove the ice water bath and stir at room temperature for 7 hours,Finally, tert-butyl 2-methyl-5-oxopyrrolidine-1-carboxylate (1.99 g, 10 mmol) was added and reacted at room temperature for 12 hours. Pour the reaction solution into saturated aqueous ammonium chloride solution,Extract with 30mL (10mL×3) ethyl acetate,Combine the organic phases, dry with anhydrous sodium sulfate,After purification by column chromatography, Int 337-1 (2.28 g, 7 mmol) was obtained with a yield of 70%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | 2-Iodo-5-fluoroanisole 5 (3.46 g, 13.0 mmol) was dissolved in 70 mL of THF, reaction mixture was cooled to -10C under nitrogen atmosphere, 2 M isopropylmagnesium chloride solution in THF (8.50 mL, 17.0 mmol) was added, stirred for 30 minutes, DMF (2.89 g, 39.1 mmol) was added, stirred for 30 minutes, reaction mixture was brought to toom temperature, 20 mL of saturated NH4Cl water solution was added. Resulting mixture was extracted with ethyl acetate (3x70 mL), extract was washed with water (5x20 mL), dried with Na2SO4. Product was isolated by column chromatography on silica gel using ethyl acetate-hexane (1:9) as eluent. Yield of 2-methoxy-4-fluorobenzaldehyde 6 was 1.9 g (94%). |
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