A kind of synthetic method of pharmaceutical intermediate diaryl sulfide compound
A synthesis method and compound technology, which is applied in the synthesis of sulfur-containing compounds, the synthesis of diaryl sulfide compounds, and the field of organic synthesis, and can solve problems that plague scientific researchers and production personnel and narrow application ranges.
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Embodiment 1
[0038]
[0039] At room temperature, in an appropriate amount of mixed organic solvent (a mixture of polyethylene glycol 200 (PEG-200) and acetonitrile with a volume ratio of 1:2), add 100 mmol of the above formula (I) compound, 150 mmol of the above formula (II) Compound, 4mmol catalyst Cu(TFA) 2 , 100mmol of base tetramethylpropylenediamine, 10mmol of the above-mentioned ligand L1 and 2mmol of auxiliary trimethyloxonium tetrafluoroborate, and then heated to 40°C under stirring, and stirred and reacted at this temperature for 7 hours.
[0040] After the reaction is completed, filter, add deionized water to the filtrate, fully shake, then extract with ethyl acetate 2-3 times, combine the organic phases, concentrate under reduced pressure, and pass the residue through 300-400 mesh silica gel column chromatography, the volume ratio is A 1:2 mixture of acetone and chloroform was used as the eluent to obtain the compound of formula (III) with a yield of 97.5%.
[0041] 1 H NM...
Embodiment 2
[0044]
[0045]At room temperature, in an appropriate amount of mixed organic solvent (a mixture of polyethylene glycol 200 (PEG-200) and acetonitrile with a volume ratio of 1:2), add 100 mmol of the above formula (I) compound, 200 mmol of the above formula (II) Compound, 7mmol catalyst Cu(TFA) 2 , 150mmol of base tetramethylpropylenediamine, 15mmol of the above-mentioned ligand L1 and 4mmol of auxiliary trimethyloxonium tetrafluoroborate, and then heated to 60°C under stirring, and stirred and reacted at this temperature for 5 hours.
[0046] After the reaction is completed, filter, add deionized water to the filtrate, fully shake, then extract with ethyl acetate 2-3 times, combine the organic phases, concentrate under reduced pressure, and pass the residue through 300-400 mesh silica gel column chromatography, the volume ratio is A 1:2 mixture of acetone and chloroform was used as the eluent to obtain the compound of formula (III) with a yield of 97.2%.
[0047] 1 H NMR...
Embodiment 3
[0050]
[0051] At room temperature, in an appropriate amount of mixed organic solvent (a mixture of polyethylene glycol 200 (PEG-200) and acetonitrile with a volume ratio of 1:2), add 100 mmol of the above formula (I) compound, 250 mmol of the above formula (II) Compound, 10mmol catalyst Cu(TFA) 2 , 200mmol of base tetramethylpropylenediamine, 20mmol of the above-mentioned ligand L1 and 6mmol of auxiliary trimethyloxonium tetrafluoroborate, and then heated to 80°C under stirring, and stirred and reacted at this temperature for 3 hours.
[0052] After the reaction is completed, filter, add deionized water to the filtrate, fully shake, then extract with ethyl acetate 2-3 times, combine the organic phases, concentrate under reduced pressure, and pass the residue through 300-400 mesh silica gel column chromatography, the volume ratio is A 1:2 mixture of acetone and chloroform was used as the eluent to obtain the compound of formula (III) with a yield of 97.7%.
[0053] 1 H N...
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