Structure of 307308-62-9
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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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CAS No. : | 307308-62-9 |
Formula : | C12H10FNO |
M.W : | 203.21 |
SMILES Code : | NC1=CC=C(OC2=CC=CC(F)=C2)C=C1 |
MDL No. : | MFCD02663349 |
Boiling Point : | No data available |
InChI Key : | OHACTALIXWVZFF-UHFFFAOYSA-N |
Pubchem ID : | 15453825 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-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 |
---|---|---|
With acetic acid; at 100.0℃; for 2.0h; | A 40 mL reaction vial was charged with a (1.85 g, 7.52 mmol), and <strong>[307308-62-9]4-(3-fluorophenoxy)aniline</strong> (1.65 g, 8.10 mmol) in 10 mL acetic acid. After being stirred at 100 C for 2 hours, volatiles were removed under reduced pressure yielding the brown residue. The residue was dissolved in methylene chloride and then washed with saturated aqueous sodium bicarbonate solution. The separated organic layer was dried over sodium sulfate and then concentrated to give (239c) as a brown residue. The resulting crude product was used to next step without purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With triethylamine; In dichloromethane; | To a solution of 4-(3- fluorophenoxy)aniline (AK Scientific, 63 mg, 0.31 mmol) in DCM 2-chloroacetyl chloride (Sigma, 42 mg, 0.37 mmol) and triethylamine (Sigma, 38 mg, 0.37 mmol) were added and the reaction stirred overnight. Upon reaction completion the crude was purified by silica gel chromatography (10-40% EtOAc/hexanes) to yield 53 mg (61%).1H NMR (400 MHz, CDCl3): d 8.24 (s, 1H), 7.55 (dq, J = 10.0, 3.5, 2.4 Hz, 2H), 7.33- 7.23 (m, 1H), 7.05 (dq, J = 10.1, 3.5, 2.6 Hz, 2H), 6.85- 6.74 (m, 2H), 6.69 (dq, J = 10.2, 2.3 Hz, 1H), 4.21 (s, 2H).13C NMR (151 MHz, CDCl3): d 164.29, 163.75, 162.66, 158.85, 158.78, 153.31, 132.67, 130.51, 130.45, 121.95, 120.13, 113.71, 113.69, 109.98, 109.84, 105.92, 105.75, 77.19, 76.97, 76.76, 42.79. HRMS: (-ESI): calcd. for: C14H10O2NFCl = 278.0390, found: 278.0389. |
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