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CAS No. : | 14135-38-7 | MDL No. : | MFCD09029446 |
Formula : | C12H8F2S2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BSLPHWROVJBMHX-UHFFFAOYSA-N |
M.W : | 254.32 | Pubchem ID : | 14740277 |
Synonyms : |
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 64.51 |
TPSA : | 50.6 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.58 cm/s |
Log Po/w (iLOGP) : | 2.8 |
Log Po/w (XLOGP3) : | 4.61 |
Log Po/w (WLOGP) : | 5.6 |
Log Po/w (MLOGP) : | 5.22 |
Log Po/w (SILICOS-IT) : | 4.5 |
Consensus Log Po/w : | 4.55 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.68 |
Solubility : | 0.00534 mg/ml ; 0.000021 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -5.4 |
Solubility : | 0.00102 mg/ml ; 0.000004 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -5.7 |
Solubility : | 0.00051 mg/ml ; 0.000002 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.52 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
45% | With C17H14O*Pd*C26H24P2S2 In melt at 100℃; for 6 h; Inert atmosphere; Green chemistry | General procedure: The melt of catalyst (5 mole percent) and appropriate aryl thiophenol (1 equiv.) was stirred under N2 atmosphere at 100 °C for 6 hours. The progress of reaction was monitored by thin layer chromatography. After 6 hours the reaction mixture was diluted with ethyl acetate and filtered through a sintered glass funnel. The filtrate was further washed with brine (X 3) and dried over Na2SO4 and concentrated under reduced pressure. The oily mass obtained was purified by column chromatography using hexane afford the desired compounds 2a-k. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With carbon disulfide; cycl-isopropylidene malonate; triethylamine; copper(l) chloride In N,N-dimethyl-formamide at 100℃; for 4 h; Inert atmosphere | General procedure: A mixture of Meldrum’s acid (1 mmol) and Et3N (2 mmol) in DMF was stirred for 15 min at r.t. Then, CS2 (1 mmol) was added and stirred for 15 min. Then, the obtained mixture was added to a stirred solution of aryl halide (1 mmol) and CuCl (0.1 mmol) in DMF (2 ml), and heated at 100 C for 4h. When the reaction was completed (TLC), the mixture was extracted with CH2Cl2 (3 3ml) and H2O (3ml). The organic layer was separated and dried (Na2SO4) and the solvent was evaporated in vacuo to give the diaryl disulfide. The product was purified by column chromatography on silica gel (EtOAc / Petroleum ether, 1:4). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With C17H14O*Pd*C26H24P2S2; In melt; at 100℃; for 6h;Inert atmosphere; Green chemistry; | General procedure: The melt of catalyst (5 mole %) and appropriate aryl thiophenol (1 equiv.) was stirred under N2 atmosphere at 100 C for 6 hours. The progress of reaction was monitored by thin layer chromatography. After 6 hours the reaction mixture was diluted with ethyl acetate and filtered through a sintered glass funnel. The filtrate was further washed with brine (X 3) and dried over Na2SO4 and concentrated under reduced pressure. The oily mass obtained was purified by column chromatography using hexane afford the desired compounds 2a-k. |
With sulfuryl dichloride; In dichloromethane; at 0℃; for 0.5h; | i) l J '-dithiobis(2-fluorobenzene')Sulfuryl chloride (0.7ml) was added dropwise to a solution of 2-fluorobenzenethiol (1.5ml) in DCM (20ml) at O0C. The reaction mixture was stirred for 30 min, then concentrated under EPO <DP n="35"/>reduced pressure. The residue was purified by chromatography on silica eluting with isohexane to give the sub-title compound as an oil, yield 1.7g. MS: APCI(+ve) 254 (M+H) | |
With N-chloro-succinimide; In dichloromethane; at 20℃; for 0.5h; | General procedure: To the stirred solution of thiols (5 mmol) in dichloromethane (10 mL),NCS (0.5 eq.) was added. The mixture was then stirred for 30 min. The progressof the reaction was monitored by TLC. After completion of the reaction, CH2Cl2(10 mL) was added and the mixture was washed successively with water (2×20mL).The organic layer was separated and dried by adding anhydrous Na2SO4.Evaporation of the solvent under reduced pressure gave almost pure product.Further purication was achieved by column chromatography on silica gel (ethyl acetate:hexane (1:30)) to give pure product in good to excellent yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | To a solution of N, N, N'- Trimethylethylenediamine (1.2 mL, 8.6 mmoles) in THF (8 mL) AT-20°C was added n-BuLi (1.6 M, 5.4 mL, 8.6 mmoles) dropwise. After 15 minutes 4- trifluoromethoxybenzaldehyde (1.5 g, 7.8 mmoles) in THF (8 mL) was added. The mixture was stirred for 15 minutes and more of n-BuLi (1.6M, 14.6 mL, 23 mmole) was added. The reaction mixture was stirred AT-20°C for 1 H, then placed in the freezer at-20°C for 20h. The mixture was COOLED TO-40°C, followed by addition OF SOLUTION OF O-FLUOROBENZENEDISULFIDE (4.0 g, 15.7 mmoles) in 30 mL THF and stirred AT-40°C TO-35°C for 3 h. The reaction was poured into 0.5 N HCI and extracted with ethyl acetate. The organic layer was washed with water and brine and then dried over NA2SO4, filtered and concentrated to give yellow oil. It was purified by silica-gel column chromatography (3 percent ETHYLACETATE/HEXANES) to give light yellow solid 1.55g (62 percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tert.-butyl lithium; In tetrahydrofuran; hexanes; at -78℃; for 1.25h; | In a flame dried flask under N2 blanket, compound B (440 mg, 1.3 [MMOL)] was dissolved in dry THF (20 mL) and cooled to-78 [°C.] A solution of t-butyl lithium (1.5 M in hexanes, 1.7 mL, 2.5 [MMOL)] was added and the reaction mixture was stirred for 15 min. 2-fluorophenyl disulfide (0.32 g, 1.3 [MMOL)] in THF (5 mL) was added and the reaction mixture was stirred at-78 [°C] for 1 h before slowly warming up to 0 [°C.] The reaction mixture was then quenched with saturated aqueous [NH4CI] (50 mL). Ethyl acetate (100 mL) was added and the layers were separated. The organic layer was washed with brine, then dried over [NA2SO4,] and concentrated to dryness. The crude product of compound C was used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydride; In DMF (N,N-dimethyl-formamide); at 20℃; for 2.2h; | To a solution of (LH-INDOL-7-YLOXY)-ACETONITRILE (0.244 g. , 1.42 mmol) in 15 mL anhydrous dimethylformamide was added sodium hydride (0.062 g. of a 60percent suspension in mineral oil, 1.56 mmol) portion wise). The solution was stirred with a magnetic stirrer at room temperature for 20 minutes. Bis- (2-fluorophenyl) disulfide (0.396 g. , 1.56 mmol) was added in one portion and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was partitioned between water (50 mL) and ethyl acetate (50 mL). The aqueous layer was extracted with ethyl acetate (2 x 25 mL) and the combined organic fractions were washed with water (2 x 25 mL) and brine (2 x 25 mL). After drying over MGS04, the organic fraction was concentrated in vacuo and the resulting dark red residue was purified by flash chromatography (chromatography (95: 5 ethyl acetate: hexanes to 85: 15 ethyl acetate: hexanes over 30 minutes) to give 0. 196 g. of [3-(2-fluoro-phenylsulfanyl)-lH-indol-7-yloxy]-acetonitrile as a clear oil. ms: (M-H)--= 297. 1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 7; Step 1: Indole (2.4 g, 20 mmol) was added to a DMF solution (100 ml_)containing NaH (0.78g) at 0°C. After stirring the solution for 15 minutes, 2-fluorophenyldisulfide (5.2g, 20 mmol) was added and the reaction mixture wasallowed to warm up to room temperature over a period of 4 h. The solvent wasremoved and the crude product was redissolved in ethyl acetate (100 ml_) andthen was washed sequentially with water (50 mL) and brine (50 ml_). The organicphase was dried and concentrated. The resulting product was recrystallized froma hexane:ethyl acetate mixture, thereby providing (7a) as a white solid (3.7 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step 4: n-butyllithium (1.6 M, 0.59 ml) was added to a solution oftrifluoroacetamide (1c) (0.16 g, 0.42 mmol) in THF at -78°C. The reaction mixturewas stirred for 0.5 h, and then 2-fluorophenyldisulfide (0.16 g, 0.63 mmol) in THF(0.6 mL) was added. The resulting mixture was stirred at -78°C for 2 h. Waterwas then added, the mixture was warmed to room temperature, and extractedwith EtOAc. The organic phases were combined, washed with water and brine,dried (anhydrous MgSO4), filtered, and concentrated under vacuum. Theconcentrated product was purified by silica gel chromatography (35percentEtOAc/hexanes) to provide a racemic intermediate product (0.13 g, 0.25 mmol).The racemic intermediate product was dissolved in DCE without furtherpurification or isolation, and m-CPBA (0.21 g, 0.84 mmol) was added thereto. Theresulting reaction mixture was stirred for 17 h at room temperature, diluted withCHaCIa, washed with water and brine, dried (anhydrous MgSO4), filtered, andconcentrated under vacuum. The resulting concentrated product was purified bysilica gel preparative plate chromatography (45percent EtOAc/hexanes) to provide (1d)(0.067 g, 0.12 mmol). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step 7: n-butlyllithium (1.8 M, 0.67 ml_) was added to a solution oftrifluoroacetamide (1g) (0.21 g, 0.54 mmol) in THF (2 ml_) which was cooled to-78°C. The reaction mixture was stirred for 30 minutes and then 2-fluorophenyldisulfide (0.17 g, 0.68 mmol) in THF (0.8 ml) was added. Thereaction mixture was allowed to slowly warm to room temperature over 17 h.Saturated NH4CI was then added, and the reaction mixture was extracted withEtOAc. The organic phases were combined and washed with water and brine,dried (anhydrous MgSO4), filtered, and concentrated under vacuum. The resultingpurified product was purified by silica gel chromatography (30percent EtOAc/hexanes)to provide a mixture of starting trifluoroacetamide and the desired thioetherproduct (0.13 g). The mixture was taken up into DCE (2 mL) without furtherpurification, and m-CPBA (0.22 g, 0.90 mmol) was added. The resulting mixturewas stirred at room temperature for 22 h. The reaction mixture was then dilutedwith CH2Cl2, washed with water and brine, dried (anhydrous MgSCU), filtered, andconcentrated under vacuum. The concentrated product was purified by silica gelchromatography (30-40percent EtOAc/hexanes) to provide (1h) (0.034 g, 0.061 mmol). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step 11: n-butyllithium (1.8 M, 0.80 mL) was added to a solution of (1j)(0.25 g, 0.64 mmol) in THF (2.1 ml), maintained at -78°C. The reaction mixturewas stirred at -78 °C for 25 minutes. 2-fluorophenyldisulfide (0.24 g, 0.96 mmol)in THF (0.8 mL) was then added to the reaction mixture. The reaction mixturewas allowed to slowly warm to room temperature over 19 h. Saturated NHUCI wasthen added, and the reaction mixture was extracted with EtOAc. The organicphases were combined and washed with water and brine, dried (anhydrousMgSdi), filtered, and concentrated under vacuum. The residue was purified bysilica gel chromatography (30percent EtOAc/hexanes) to provide the thioether (0.23 g,0.44 mmol). The thioether was taken up into DCE (3 mL) without furtherpurification or isolation, then m-CPBA (0.38 g, 1.54 mmol) was added and themixture stirred at room temperature for 24 h. CH2CI2 was then added to themixture, and the mixture was washed with water and brine, and the organic layerwas dried (anhydrous MgSO4), filtered, and concentrated under vacuum. Theresidue was purified by silica gel chromatography (35percent EtOAc/hexanes) toprovide (1k) (0.13 g, 0.23 mmol). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 17 (+)-(4aR)-(10bR)-8-(2-fluorophenylthio)-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one A 700 mg portion of the same starting material used in Example 5 was reacted with 2.4 g of bis(2-fluorophenyl)-disulfide under the conditions of Example 5 to obtain 640 mg of the desired product. mp 196°-198° FDMS: m/e=341. alpha[D]589 =+84.2, alpha[D]365 =+300.8 (chloroform). | ||
EXAMPLE 17 (+)-(4aR)-(10bR)-8-(2-fluorophenylthio)-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one STR31 A 700 mg portion of the same starting material used in Example 5 was reacted with 2.4 g of bis(2-fluorophenyl)disulfide under the conditions of Example 5 to obtain 640 mg of the desired product. mp 196°-198° FDMS: m/e=341. alpha[D]589 =+84.2, alpha[D]365 =+300.8 (chloroform). | ||
EXAMPLE 17 (+)-(4aR)-(10bR)-8-(2-fluorophenylthio)-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one A 700 mg portion of the same starting material used in Example 5 was reacted with 2.4 g of bis(2-fluorophenyl)disulfide under the conditions of Example 5 to obtain 640 mg of the desired product. mp 196°-198° FDMS: m/e=341. alpha[D]589 =+84.2, alpha[D]365 =+300.8 (chloroform). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
i) 4-bromo-2-fluoro- 1 - [Y.sum.-fluorophenvDthioibenzene4-Bromo-2-fluoro-l-iodobenzene (1.67g) was added to a solution of isopropylmagnesium chloride (2.79ml, 2M solution in THF) in THF (8ml), which was cooled to O0C and stirred for a further 2h. The mixture was then added to a solution of the product of step (i) in THF (5ml). The reaction was allowed to reach RT overnight, then stirred at 4O0C for 1 hour and 500C for a further 1 hour. The reaction was cooled to RT, diluted with ammonium chloride and extracted with diethylether. The diethylether fractions were dried (MgSO4) and evaporated under reduced pressure, yield 1.9g. Used directly without further purification. MS: APCI(+ve) 302 (M+H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Compound 10. In a flame dried flask under N2 blanket, Compound 5 (21.55 g, 50.7 mmol) was dissolved in anhyd THF (300 mL) and cooled in a dry ice/IPA bath. A solution of methyllithium (1.6 M in Et2O, 32 mL, 51 mmol) was added, followed by n-BuLi (2.5 M in hexanes, 20.3 mL, 50.7 mmol) and the reaction mixture was stirred for 10 min. A solution of bis-(2-fluorophenyl) disulfide (14.2 g, 55.7 mmol) dissolved in THF was added and the reaction mixture was stirred for 2 h at -78 C. The ice bath was removed and the reaction mixture was allowed to warm to rt and left stirring overnight. The reaction mixture was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The organic layer was dried with Na2SO4 and the solvents were evaporated. The crude product was purified via sgc (25percent EtOAc/hexanes) to give 23.2 g of a solid. This material was dissolved in CH2Cl2 (400 mL) and cooled in an ice bath. MCPBA (60percent, 30.3 g) was added in several portions and the reaction mixture was stirred for 1 h. The ice bath was removed and the reaction mixture was left stirring overnight. The reaction mixture was partitioned between CH2Cl2 and 5percent aq Na2CO3. The organic layer was washed with water and dried with Na2SO4. The solvents were evaporated and the crude product was purified via sgc (25percentEtOAc/hexanes) to give 10.84 g (44percent) of Compound 10. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Compound 1 (3 g, 0.026 mol) was dissolved in DMF (150 mL), and cooled to 0° C. NaH (dry, 95percent, 0.97 g, 0.038 mol) was added, and the reaction was stirred for 15 min. A solution of 2-fluorophenyl disulphide (6.5 g, 0.026 mol) in DMF (5 mL) was added, and the reaction was allowed to proceed at r.t. overnight. The reaction was quenched with H2O. Solvent was removed. CH2Cl2 was added to dilution the reaction mixture. The organics were extracted with brine (50 ml.x.2) and H2O (50 ml.x.2). The organic layer was dried over Na2SO4 and concentrated to dryness. The crude product was purified via (10percent EtOAc/hexanes) to give 5.33 g (85percent) of compound 2 as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | To a solution of Compound 68 (380 mg, 0.92 mmol) in THF (10 mL) at -78° C. was added n-BuLi (0.81 mL, 2.5 M in hexanes, 2.0 mmol). The solution was stirred at -78° C. for 30 min. Bis(2-fluorophenyl) disulfide (467 mg, 1.84 mmol) in THF (5 mL) was added dropwise. The reaction mixture was allowed to warm slowly to rt, and was stirred for 18 h. The reaction mixture was diluted with EtOAc and washed with water and brine, dried over Na2SO4, and filtered. Evaporation of the solvent gave a crude solid that was then purified by sgc (3:1 hexanes-EtOAc) to give 400 mg (81percent) of Compound 69. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | n-BuLi (4.7 mL, 2.5 M in hexane, 12 mmol) was added dropwise over 10 min to a solution of Compound 7 (2.33 g, 5.55 mmol) in THF (50 mL) at -78° C. The resulting solution was stirred at -78° C. for 30 min. A solution of <strong>[14135-38-7]bis(2-fluorophenyl) disulfide</strong> (1.4 g, 5.5 mmol) in THF (40 mL) was added by cannula and the reaction mixture was stirred at -78° C. for 5 h, and then allowed to warm to rt over 12 h. The reaction mixture was neutralized with saturated aq NaHSO4 solution and was partitioned between water (200 mL) and EtOAc (200 mL). The aq. layer was extracted again with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, and filtered. The solvent was evaporated to a solid. After purification by sgc (2:1 hexane-EtOAc), 2.52 g (83percent) of Compound 8 was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37%; 31% | General procedure: CuBr (0.043g, 30molpercent), L (0.057g, 30molpercent), t-BuOLi (0.16g, 2equiv.) were placed in DMSO (4mL). The mixture was stirred at room temperature for 10min. Then 2 (1mmol) or 6 (0.5mmol) was added and the reaction flask was evacuated and refilled with O2 three times, stirred for 10min at RT. Pentafluorobenzene 1 (0.42g, 2.5mmol) was added in turn to the flask using syringes. The reaction mixture was stirred at 100°C under an atmosphere of oxygen for 8h. After cooling down, the reaction mixture was diluted with 20mL of ethyl ether, filtered through a pad of silica gel, followed by washing the pad of the silica gel with the same solvent (20mL). The filtrate was washed with water (3×15mL). The organic phase was dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure. The residue was then purified by flash chromatography on silica gel to provide the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With dihydrogen peroxide; iodine; In ethanol; at 25℃; for 18h;Green chemistry; | General procedure: A 15-mL tube with a Teflon cap, equipped with a magnetic stirring bar, was charged with substrate 1a (0.20 mmol), diphenyl disulfide (0.10 mmol, 0.5 equiv), and I2 (20 mol percent); H2O2 (2 equiv) and EtOH (2mL) were then added sequentially. The tube was capped and stirred at 25 °C for 18 h, the crude mixture was diluted with EtOAc, and washed with sat. aq Na2S2O3 solution (3 × 10 mL). The organic phase was dried (MgSO4), filtered through a Celite pad, and washed with EtOAc. The filtrate was concentrated in vacuo, and the resulting residue was purified by column chromatography (hexane ? EtOAc) to afford product 3aa as a light yellow solid; yield: 56.8 mg (92percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With oxygen; copper dichloride; In water; N,N-dimethyl-formamide; at 100℃; under 759.826 Torr; for 24h; | General procedure: To a Schlenk tube were added N-(p-methoxyaryl)propiolamide1a (0.2 mmol), 1,2-diphenyldisulfane (2a, 1.5 equiv), H2O (2equiv), CuCl2 (10 molpercent), and DMF (anhydrous; 2 mL). Then thetube was charged with oxygen and was stirred at 100 °C for 24h until complete consumption of starting material as monitoredby TLC and/or GC?MS analysis. After the reaction was finished,the reaction mixture was washed with brine. The aqueousphase was re-extracted with EtOAc. The combined organicextracts were dried over Na2SO4, concentrated in vacuum, andthe resulting residue was purified by silica gel column chromatography(hexane?EtOAc) to afford the desired product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With tert.-butylhydroperoxide; di-tert-butyl peroxide; at 120℃; for 24h; | General procedure: Under air atmosphere, disulfides or diselenides (0.3mmol), DTBP (1.0 eq.) TBHP (2.0 eq.) and acetone (2 mL) were added to a screw-cappedvial. The reaction vial was placed in a temperature-controlled aluminum-heatingblock set at 120 oC. The reaction progresswas monitored by TLC. After the completion of the reaction, the vial was removedfrom the heating block and was left to cool to the ambient temperature. Thesolution was filtered though a short column of silica gel and washed withEtOAc. The filtrate was concentrated under reduced pressure to leave a crudeproduct, which was purified by flash column chromatography on silica gel with Petroleumether/EtOAc as an eluent to give the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | General procedure: The benzamide (0.2 mmol), NaH (3 equivalents) and dry THF(3 mL) were added to a two-neck flask in turn and stirred atroom temperature for 1 h. Then disulfide (1.5 equivalent) wasadded into the mixture and stirred for another 36 h at roomtemperature. During the whole reaction process, the systemwas kept turbid because of the difficult solubility of NaH inTHF. Then the resulting mixture was filtered and washed withEtOAc to give the solvent, which was concentrated in vacuoand the residue was purified by flash column chromatographyon a silica gel to give the desired product | |
With sodium hydride; In tetrahydrofuran; at 20℃; for 36h; | General procedure: The benzamide (0.2 mmol), NaH (3 equiv.) and dry THF (3 mL ) were added to a two necked flask in turn and stirred at room temperature for 1h. Then disulfide (1.5 equiv.) was added into the mixture and stirred for another 36 h at room temperature. During the whole reaction process, the systemwas kept turbid owing to the difficult solubility of NaH in THF. Then theresulting mixture was filtered and washed with EtOAc to give the solvent, which was concentrated in vacuo and the residue was purified by flash columnchromatography on a silica gel to give the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With iodine; potassium acetate; at 90℃; for 12h; | General procedure: A 15-mL tube with a Teflon cap, equipped with a magnetic stirring bar, was charged with substrate 1 (0.20 mmol), iodine (0.40 mmol, 2.0 equiv), KOAc (1.0 mmol, 5.0 equiv) in MeNO2 (1mL) was then added sequentially. The tube was then capped and stirred at 90 °C for 12 h. the crude mixture was diluted with AcOEt, and washed with sat. aq Na2S2O3 solution (3 × 10 mL). The organic phase was dried (MgSO4), filtered through a Celite pad, and washed with AcOEt. The filtrate was concentrated in vacuo, and the resulting residue was purified by column chromatography,(hexane-EtOAc) to afford product 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With iodine; copper(II) bis(trifluoromethanesulfonate); In dimethyl sulfoxide; at 120℃; for 6h; | 52 mg (0.5 mmol) of styrene, 63.5 mg (0.25 mmol) of <strong>[14135-38-7]2,2'-difluorodiphenyl disulfide</strong>, 18.1 mg (0.05 mmol) of Cu (OTf) 2, 127 mg (0.5 mmol) of iodine In the reaction tube, 2 mL of DMSO was added and heated at 120 ° C for 6 hours. After the reaction was allowed to cool, the filtrate was washed with water to remove excess iodine and solvent. The organic phase was combined and distilled. The resulting residue was chromatographed on silica gel. The solvent was distilled off by rotary evaporator and dried in vacuo to give 87.4 mg of trans-2- (2'-fluoro) -phenylthioacetate as a yellow liquid in 76percent yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With carbon disulfide; cycl-isopropylidene malonate; triethylamine; copper(l) chloride; In N,N-dimethyl-formamide; at 100℃; for 4h;Inert atmosphere; | General procedure: A mixture of Meldrum?s acid (1 mmol) and Et3N (2 mmol) in DMF was stirred for 15 min at r.t. Then, CS2 (1 mmol) was added and stirred for 15 min. Then, the obtained mixture was added to a stirred solution of aryl halide (1 mmol) and CuCl (0.1 mmol) in DMF (2 ml), and heated at 100 C for 4h. When the reaction was completed (TLC), the mixture was extracted with CH2Cl2 (3 3ml) and H2O (3ml). The organic layer was separated and dried (Na2SO4) and the solvent was evaporated in vacuo to give the diaryl disulfide. The product was purified by column chromatography on silica gel (EtOAc / Petroleum ether, 1:4). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With dipotassium peroxodisulfate; iodine; dibenzoyl peroxide; In nitromethane; at 120℃; for 24h;Inert atmosphere; | 41.6 mg (0.2 mmol) of 1,3-diphenylpropynol, 50.9 mg (0.2 mmol) of bis(2-fluorophenyl)disulfide 14.5 mg (0.06 mmol) of benzoyl peroxide, 101.6 mg (0.4 mmol) of iodine, 108.1 mg (0.4 mmol) of potassium persulfate was added to the reaction tube, 2 mL of nitromethane was added, and the reaction tube was filled with N2. 120 ° C for 24 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, the organic layer was dried over anhydrous MgSO4, filtered and the filtrate was evaporated to dryness. The solvent was removed and the residue was chromatographed on silica gel using a petroleum ether and ethyl acetate volume ratio of 200: 1 mixture of the eluent, the effluent was collected according to the actual gradient, TLC detected, and the product-containing effluent was combined. The solvent was distilled off on a rotary evaporator and dried in vacuo to give 40.6 mg of 2-(2-fluorophenylthio)-3-phenylinden-1-one as a red solid in 61percent yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In tetrahydrofuran; at 80℃; for 4h;Inert atmosphere; Sealed tube; | General procedure: Under N2, a 20 mL Schlenk tube equipped with a stir bar was charged with diphenylphosphine oxide 1 (0.2 mmol), diphenyl sulfide 2 (0.2 mmol), THF (2.0 mL). The tube was sealed with a Teflon cap. The reaction mixture was stirred at 80 C for 4 h in oil bath. After the completion of the reaction (monitored by TLC), the reaction mixture was concentrated in vacuum and the residue was purified by flash column chromatography on silica gel with petroleum ether-EtOAc as the eluent to give the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With iodine; sodium carbonate; In dimethyl sulfoxide; at 100℃; for 24h;Green chemistry; | A solution of 50.8 mg (0.2 mmol) of o-fluorodiphenyl disulfide, 40.5 mg (0.4 mmol) of triethylamine, 42.4 mg (0.4 mmol) of Na2CO3, 101.6 mg (0.4 mmol) of iodine was added in the reaction tube, 2 ml of DMSO was added , heated at 100OC for 24 hours. After completion of the reaction was cooled, filtered, and the filtrate was rotary evaporated to remove the solvent, the residue was purified by silica gel column chromatography, petroleum ether Elution, TLC detection, the combined product containing effluent, rotary evaporator to remove the solvent, vacuum drying to be yellow liquid 26.1 mg 2,2-bis-fluorophenylthioacetaldehyde, the yield of 44percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With iron(III) chloride; iodine; dibenzoyl peroxide; In nitromethane; at 120℃; for 12h;Schlenk technique; Inert atmosphere; | General procedure: To a flame-dried Schlenk tube with a magnetic stirring bar wascharged with 1 (0.1 mmol), 2 (0.2 mmol), FeCl3 (6.4 mg, 0.04mmol), BPO (0.02 mmol, 4.8 mg), and I2 (101.6 mg, 0.4 mmol) in MeNO2 (2 mL) under N2 atmosphere. The reaction mixture was stirred at 120°C until complete consumption of starting material as detected by TLC or GC-MS analysis. After the reaction was finished, the mixture was poured into EtOAc, which was washed with sat. Na2S2O3 (2 × 15 mL) and brine (1 × 15 mL). After the aqueous layer was extracted with EtOAc, the combined organic layers were dried over anhydrous Na2SO4, and evaporated under vacuum. The residue was purified by flash column chromatography (PE?EtOAc) to afford the desired products 3-20. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With iodine; sodium carbonate; In dimethyl sulfoxide; at 100℃; for 24h;Schlenk technique; | General procedure: Under air atmosphere, a reaction tube was charged with disulfide (0.2 mmol), Tertiary amine (0.4 mmol), I2 (0.4 mmol) Na2CO3 (0.4 mmol) and DMSO (2 mL). The vessel was sealed and heated at 100 °C (oil bath temperature) for 24 h and then cooled to room temperature. The reaction mixture was washed with saturated Na2S2O3(2 x 15 mL) and then brine (1 x 15 mL). After the aqueous layer was extracted with ethyl acetate, the combined organic layers were dried over anhydrous Na2SO4 and evaporated under vacuum. The residue was purified by flash column chromatography (hexane/ethyl acetate) to afford the desired products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27% | With dipotassium peroxodisulfate; In water; acetonitrile; at 90℃; for 24h;Inert atmosphere; Schlenk technique; | General procedure: To a 25 mL Schlenk tube were added aryl alkynoates 1 (0.2 mmol), disulfides 2 (0.3 mmol, 1.5 equiv), K2S2O8 (0.6 mmol, 3.0 equiv) and CH3CN/H2O (1:1, 2 mL). Then the tube was charged with nitrogen, and the reaction mixture was stirred at 90 °C for 24 h until entire consumption of substrates as monitored by TLC. The resulting mixture was extracted with ethyl acetate. The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuum. The resulting residue was purified by column chromatography on silica gel (eluent: petroleum ether/ethyl acetate) affording the desired product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With silver hexafluoroantimonate; In 1,2-dichloro-ethane; at 100℃; for 9h;High pressure; | At room temperature, isoquinoline-1 (2Eta)-one (10 mmol), bis(2-fluorophenyl)disulfide was sequentially added to a pressure-resistant reaction tube. Ether (10 mmol), silver hexafluoroantimonate (ll mmol) and dichloroethane (6 mL). The reaction mixture is then reacted at 100 C for 9 hours. Time. The reaction was stopped, concentrated under reduced pressure to give a crude product, and finally rinsed with a mixture of petroleum ether and ethyl acetate. Chromatography gave the corresponding product 4-(2-fluorophenylthio)isoquinolin-1(2H)-one. Yield 90%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With copper diacetate; In N,N-dimethyl-formamide; at 100℃; for 24h; | 2-[(o-fluorophenylthio)methyl]-1-toluenesulfonic acid indoline: In a 10 mL tube reactor,Substrate 1 (0.2 mmol, 57.4 mg),2 (0.3 mmol, 72.3 mg),Cu(OAc) 2 (0.02 mmol, 4.0 mg),Weigh the reaction tubes in turn,Then 3 mL of DMF was added.The reaction system is heated to 100 ° C,Reaction for 24 hours.After TLC detects the reaction,The system was cooled to room temperature.Add saturated NH4Cl solution,Extract three times with ether,Spin the organic phase,Column chromatography gave 52.9 mg of a white solid.The yield was 64percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With copper(l) iodide; XPhos; In dimethyl sulfoxide; at 120℃; for 24h;Sealed tube; Schlenk technique; | General procedure: Under an air atmosphere, a reaction tube was charged with 2-(1H-pyrrol-1-yl)pyridine (1a) (0.2 mmol), diphenyldisulfane (2a) (0.4 mmol), CuI (10 molpercent), XPhos (2-dicyclohexylphosphino-2?,4?,6?-triisopropylbiphenyl) (10 molpercent) and DMSO (2 mL). The vessel was sealed and heated at 120 °C (oil bath temperature) for 24 h and then cooled to room temperature. The reaction mixture was washed withs aturated Na2S2O3 (2 × 15 mL) and then brine (15 mL). After the aqueous layer had been extracted with EtOAc, the combined organic layers were dried over anhydrous Na2SO4 and evaporated under vacuum. The residue was purified by flash column chromatography (hexane/EtOAc) to afford the product 3a. |
Tags: 14135-38-7 synthesis path| 14135-38-7 SDS| 14135-38-7 COA| 14135-38-7 purity| 14135-38-7 application| 14135-38-7 NMR| 14135-38-7 COA| 14135-38-7 structure
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