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CAS No. : | 2251-50-5 | MDL No. : | MFCD00000657 |
Formula : | C7ClF5O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MYHOHFDYWMPGJY-UHFFFAOYSA-N |
M.W : | 230.52 | Pubchem ID : | 75256 |
Synonyms : |
|
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P264-P301+P330+P331-P305+P351+P338-P363-P403-P501 | UN#: | 3265 |
Hazard Statements: | H314 | Packing Group: | Ⅱ |
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 |
---|---|---|
100% | With thionyl chloride; for 2h;Reflux; | General procedure: A mixture of various carboxylic acids (1.0mmol), an excess of thionyl chrolide (5mL) was refluxed for 2h and concentrated in vacuo to give corresponding acyl chloride (quant). |
> 99% | With thionyl chloride; for 3h;Reflux; | Solid C6F5CO2H (5.00 g, 23.58 mmol) was added portionwise to SOCl2 (20 mL, 274.19 mmol) at room temperature and then was refluxed for 3 h. All volatile materials were removed under reduced pressure resulting to yellowish low melting glassy solid, C6F5COCl (5.42 g, >99%). The substance was pure and used without further purification. 19F NMR (376.498 MHz, CDCl3): delta=135.64 to 135.68 (m, 1F), 137.38 to 137.48 (m, 1F), 143.33 to 144.94 (m, 1F), 158.84 to 159.05 (m, 2F) ppm. |
75% | With phosphorus pentachloride; for 2h;Reflux; | Pentafluorobenzoic acid (1) (20.2 g, 95 mmol) and PCl5 (21.9 g, 105 mmol) were refluxed with stirring for 2 h. The title product was distilled in vacuo, collecting the first fraction (51-53 C/ 14 Torr) (60-67 C/ 23 Torr [35]). Colorless liquid, yield: 16.4 g (75 %). |
With thionyl chloride; In dichloromethane; for 4h;Reflux; | General procedure: SOCl2 (1.65 mL) was added to a solution of benzoic or phenylaceticacid derivatives (2 mmol) in dry CH2Cl2 (1.65 mL), and thesuspension was refluxed for 4 h. The resulting solution was evaporated,the residue was dissolved in dry acetone (10 mL) and 3-(4-aminophenyl)-7-hydroxy-coumarin 4 (0.51 g, 2 mmol) was added.The mixture was refluxed with anhydrous K2CO3 (1.104 g, 8 mmol)for 4 h. Acetone was removed under reduced pressure and coldwater (20 mL) was added. 3 N HCl was added until the solutionbecame acidic. The resulting precipitate was filtered, washed withwater and recrystallized from methanol or ethanol to give thedesired products 5a-k. | |
With sulfuryl dichloride; for 3h;Reflux; | a) Synthesis of C6F5C(O)Cl. At 0 C C6F5CO2H (3.00 g, 14.2 mmol)was added portionwise to SOCl2 (5.20 mL, 70.7 mmol) (Attention HCl and SO2 evolution) and the mixture obtained was refluxed for3 h, then all volatile materials were removed under reduced pressure. The C6F5C(O)Cl obtained (3.20 g, >99%) as a gray powder was used further without additional purification. | |
With thionyl chloride; at 20℃; for 12h; | Thionyl chloride is used as an acid chlorination reagent. The addition amount is 5 times the molar amount of pentafluorobenzoic acid. Thionyl chloride is added to the flask containing pentafluorobenzoic acid. After the dropwise addition, the mixture is stirred at room temperature.After 12 hours of reaction, the product was distilled under reduced pressure to remove excess sulfoxide,Compound (II) pentafluorobenzoyl chloride is obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | In dichloromethane at 20℃; for 8.5h; Inert atmosphere; | Synthesis of receptor L 2,3,4,5,6-Pentafluorophenylhydrazine (5 mmol) was dissolvedin 25 ml of dichloromethane (DCM) with constantstirring at room temperature (RT), and 2,3,4,5,6-pentafluorobenzoylchloride(5 mmol) 25 mL of DCM was added dropwise30 min under inert atmosphere. After 8 h of constantstirring, sandal yellow turbid-containing solution is threetimes washed with 50 ml of water to remove ethylene triaminehydrochloride (Et3N·HCl). Washed organic layer isevaporated to obtain the product. The 1H-NMR spectroscopy,infrared (IR) spectroscopy and elemental analysis dataof receptor L match with their proposed formulation. Yield:79% 1H-NMR (400 MHz, DMSO-d6): δ 8.53 and 11.104 ppmfor amide-NH-NH- and PF-Ar-NH-NH- resonances.Elemental analysis: C13H2F10N2O:Calculated C = 39.82;H = 0.51; F = 48.45; N = 7.14; O = 4.08: Experimental:C = 40.18%; N = 7.08 and O = 3.98. IR Analysis:3282 cm-1, and 3336 cm-1 for amide-NH-NH- andPF-Ar-NH-NH- (See supporting information). |
In benzene for 1h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19% | With aluminium trichloride In dichloromethane at 23℃; for 8h; | |
In dichloromethane for 4.5h; | 1A Improved Benzo[b]thiophene Derivative Syntheses Compound 15A-3-(2',3',4', 5',6'-pentafluorobenzoyl)-2-(4'-methoxyphenyl)-6-methoxybenzo[b]thiophene (see FIG. 18) was synthesized as follows. To a well-stirred solution of 2-(4'methoxyphenyl)-6-methoxybenzo[b]thiophene (0.538 g, 1.989 mmol) and 2,3,4,5,6-pentafluoro benzoyl chloride (1.000 g, 4.338 mmol) in CH2Cl2 (80 ml) was added AlCl3 (2.147 g, 16.103 mmol) portionwise over a 5 min period. After 4.5 h, water was added, and the product was isolated initially by extraction with CH2Cl2 and subsequently by extraction with EtOAc. The organic layers were washed separately with brine and then combined and dried over MgSO4. Purification by flash chromatography (silica gel, 90:10 hexane/EtOAc then with 80:20 hexane/EtOAc) afforded the desired product (0.5086 g, 60%) as a yellow colored solid. Recrystallization with ethylacetate/hexane mixture, gave highly pure product (0.206 g). 1H-NMR (CDCl3, 360 MHz) d 8.47 (d, J=9.0 Hz, 1H, ArH), 7.30 (d, J=2.4 Hz, 1H, ArH), 7.24 (d, J=8.8 Hz, 2H, ArH), 7.16 (dd, J=9.0, 2.2 Hz, 1H, ArH), 6.77 (d, J=8.8, Hz, 2H, ArH), 3.91 (s, 3H, -OCH3), 3.78 (s, 3H, OCH3). HRMS (EI) M+ calcd for C23H13O3SF5 464.0537, found 464.0506. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With ammonia; In water; at 20℃; for 0.5h; | To the saturated aqueous solution of ammonia (70 mL) in a 100 mL glass pentafluorobenzoyl chloride (2) (8.5 g, 37 mmol) was carefully added dropwise with intensive stirring at r.t. The abundant white precipitate was filtered out in vacuo, washed with water 5 times and air dried to a constant weight. White solid; yield: 7.1 g (92 %); mp 147.4-147.7 C (150 C [35]). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 190℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In hexane at 55℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In hexane at 55℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In hexane at 55℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | In tetrahydrofuran; at 20℃; for 0.5h; | Following the general procedure described above, reaction of pentafluorobenzoyl chloride (6.92 g, 30.0 mmol) with 2-mercaptopyridine (3.33 g, 30.0 mmol) in THF (30 mL) for 30 min at room temperature afforded pale yellow solid after precipitation (7.97 g, 87%): mp 51 C.; 1H NMR delta 7.37-7.42 (m, 1H), 7.75-7.79 (m, 1H), 7.81-7.87 (m, 1H), 8.67-8.71 (m, 1H); Anal. Calcd for C12H4NOS: C, 47.22; H, 1.32; N, 4.59. Found: C, 47.59; H, 1.29; N, 4.38. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With pyridine In benzene at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | 2-(perfluorophenyl)benzo[d]oxazole was produced as a white solid in 33% yield. 2- (perfluorophenyl)benzo[d]oxazole was prepared by following the literature procedure (Senaweera et al., 2014). Triethylamine (1.7 g, 16.9 mmol) was added dropwise to a solution of 2-aminophenol (1.4 g, 12.7 mmol) and pentafluorobenzoyl chloride (3.2 g, 14.1 mmol) in ethyl acetate (50 mL). The mixture was refluxed overnight and then aq NaOH (1M, 30 mL) was added and stirred for 3 hours at room temperature. The resulting mixture was extracted with EtOAc (5 x 20 mL) and washed with H20 (25 mL) and brine (25 mL). The organic layer was dried over anhydrous MgSO4 to yield 4 g of intermediate. Next, P205 (4.0 g, 28 mmol) was added to the intermediate and then heated at 175C for 1 hour. After the mixture had cooled to room temperature, ice water (50 mL) was added and mixture was extracted with EtOAc (5 x 20 mL). The combined organic layers were washed with aq NaOH (0.25 M, 50 mL), followed by water, brine and dried over anhydrous MgSO4 and then concentrated in vacuo to afford the crude product. The resultant crude residue was purified by automated flash chromatography (hexane:EtOAc 90:10) to give the product (1.2 g, 4.2 mmol), which matches with NMR spectra of product reported in the literature (Tanaka et al., 2001). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10% | With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63.4% | With hydrazine hydrate; In 1-methyl-pyrrolidin-2-one; at -10℃; | Perfluorobenzoylchloride (PFBC) 23.5 g (102 mmol) and N-methyl-2-pyrrolidinone (NMP) 100 mL were charged into a 250 mL flask equipped with a dropping funnel and a nitrogen gas inlet tube. The flask was cooled to -10 C. and N2H4.H2O 2.6 g (52 mmol) was dropwise added slowly to the flask under stirring condition. On completion of the dropping addition, the mixture was reacted at -10 C. for 6 hours. Next, the reaction mixture was added to excess water, filtered, and dried. The obtained product was recrystallized twice using methanol and water to produce a white crystal of 10F-BH (yield 63.4%). The melting point of 10F-BH was 270.3 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | In tetrahydrofuran at 0 - 20℃; for 2h; | |
68% | In tetrahydrofuran at 0℃; for 1.75h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | 1,9-Bis(pentafluorobenzoyl)-5-(pentafluorophenyl)dipyrromethane (2). A sample of 5-pentafluorophenyldipyrromethane (1) (1.87 g, 6.00 mmol) was placed in oven-dried round bottom flask. The flask was purged with argon for 10 min and anhydrous toluene (12 mL) was added with an oven dried glass syringe. The resulting solution was stirred at room temperature for 10 min and cooled to 0 C. MesitylMgBr (25.2 mmol, 25.2 mL, 1 M in THF) was added dropwise to this cooled solution. The mixture was stirred for 30 min at 0 C. and a sample of pentafluorobenzoyl chloride (1.76 mL, 12.2 mmol) was added. The resulting reaction mixture was stirred 1 h at 0 C. Over this time, the solution turned to dark ink-blue. The reaction mixture was poured into a saturated aqueous NH4Cl (~200 mL) solution that was pre-cooled to 0 C. The reaction mixture turned dark brown in 5 min. Ethyl acetate (~200 mL) was added. The organic phase was washed with water and brine, dried over Na2SO4, and concentrated to dryness to afford a brown paste. The crude product was dissolved in ethyl acetate (5 mL) and CH2Cl2 (20 mL) was added slowly. The solution was allowed to stand for 20 min. The resulting precipitate was filtered and dried under vacuum to give a white powder (2.91 g, 69%). 1H NMR, 13C NMR and ESI-MS analytical data are consistent with that reported in the literature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine In dichloromethane at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With triethylamine In dichloromethane at 0℃; for 0.5h; | |
89% | With pyridine In dichloromethane at 0℃; Inert atmosphere; Sealed tube; | |
With triethylamine In dichloromethane at 0℃; Cooling with ice; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
> 100% | With (piperidinomethyl)-polystyrene; In tetrahydrofuran; for 2.16667h; | A mixture of 4-[3-aminobenzoyl]-1-methylpiperidine (25 mg, 0.115 mmol) and (piperidinomethyl)-polystyrene (100 mg, 0.260 mmol) in tetrahydrofuran (2 mL) was allowed to stand for 10 min. Pentafluorobenzoyl chloride (33 muL, 0.229 mmol) was added to the reaction mixture. The reaction mixture was mixed for 2 h at ambient temperature. The reaction mixture was filtered and the filter cake was rinsed with methanol. Glacial acetic acid (0.5 mL) was added to the filtrate solution and the solution was mixed. This mixture was poured over a Varian Mega Bond Elut strong cation exchange column. The column was rinsed with methanol to remove impurities, then treated with a 7M ammonia in methanol to elute the product from the column. The solvent was evaporated to give 51 mg (>100%) of the title compound. [00559] MS(m/e): 413 (M+1), 411 (M-1). [00560] The compounds of Examples 48 through 66 were prepared by the procedure described in detail in Example 47. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With aluminum (III) chloride; In dichloromethane; at 15 - 20℃; for 1.16667h;Heating / reflux; | 473 mg of pentafluorobenzoyl chloride (1.90 mmol) are dissolved in 20 ml of dichloromethane, cooling to 15C under stirring, then added with 274 mg of anhydrous AlCl3 (2.05 mmol) finely powdered. Afterwards 0.5 g of 9,9-spirobifluorene (1.58 mmol) dissolved in 10 mi of dichloromethane are added drop wise under stirring in a period of 10 minutes. The reaction mixture is allowed reaching room temperature (RT) then heated, refluxing for 1 hour. The solvent is evaporated off under vacuum and the residue is added with 50 g of ice and 25 ml of a solution 2N of HCl. The aqueous phase is extracted with CH2Cl2 (3 x 15 ml). The combined organic phases are washed with a saturated solution of NaHCO3 (20 ml), water (20 ml), dried and concentrated to obtain a solid residue. The product is purified by silica chromatography with eluant hexane: CH2Cl2 70 : 30, to obtain 482 mg of 2-(pentafluoro)-benzoyl-9,9-spirobifluorene (C32H15F50]; MW = 510.46; yields of 60 %).1 H-NMR (CDCl3, 200 MHz, delta vs SiMe4) : 6.80- 8.00 (15 H, mc, ArH). 13C-NMR (CDCl3, 50 MHz, delta vs SiMe4): 184.33 (C=O), 150.61, 149.98, 148.71, 147.32, 141.92, 140.03, 139.75, 135.35 (all quaternary carbons), 130.91, 129.91, 129.06, 128.16, 128.03, 124.95, 124.57, 124.39, 123.93, 121.34, 120.63, 120.26, 120.15 (all CH), 65.90 (C-spiro). IR (CCl4, cm-1): 1677 (C=O). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With aluminum (III) chloride; In dichloromethane; at 15 - 20℃; for 1.16667h;Heating / reflux; | 870 mg of pentafluorobenzoyl chloride (3.48 mmol) are dissolved in 20 mi of dichloromethane, cooling to 15C under stirring, then added with 695 mg of anhydrous AlCl3 (5.21 mmol) finely powdered. Afterwards 0.5 g of 9,9-spirobifluorene (1. 58 mmol) dissolved in 10 ml of dichloromethane are added drop wise under stirring in a period of 10 minutes. The reaction mixture is allowed reaching room temperature (RT) then heated, refluxing for 1 hour. The solvent is evaporated off under vacuum and the residue is added with 50 g of ice and 25 ml of a solution 2N of HCl. The aqueous phase is extracted with CH2Cl2 (3 x 15 ml). The combined organic phases are washed with a saturated solution of NaHCO3 (20 ml), water (20 ml), dried and concentrated to obtain a solid residue. The product is purified by silica chromatography with eluant hexane: CH2CI2 70:30, to obtain 760 mg of 2,2'-di-(pentafluoro)-benzoyl-<strong>[159-66-0]9,9'-spirobifluorene</strong> (C39H14F1002 MW = 704.53; yields of 69 %). 1H-NMR (CDCl3, 200 MHz, delta vs SiMe4): 6.80-8.00 (14 H, mc, ArH), 13C-NMR (CDCI3, 50 MHz, delta vs SiMe4): 184.31 (C=O), 149.01, 148. 70, 148.57, 139.86, 135.44 (all quaternary carbons), 131.43, 130.11, 128. 60, 124.64, 124.26, 121.63, 120.45 (all CH), 65.68 (C-spiro). IR (CCI4, cm-1): 1674 (C=O). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With aluminum (III) chloride; In dichloromethane; at 0 - 20℃; | To a stirred slurry of AIDS (0.56 g, 4.18 mmol) in anhydrous dichloromethane (40 ml) at 0 C and under Ar was added drop wise 4-pentafluorobenzoyl chloride (0.53 ml, 3.7 mmol). To this cooled mixture was added drop-wise a sample of 5-thiophen-2- YLMETHYL-LH-PYRROLE-2-CARBALDEHYDE (16) (0.31 g, 1.62 mmol) dissolved in anhydrous dichloromethane (5ml). The mixture was then stirred overnight at room temperature, during this time a sticky substance came out of solution. The light-brown crude reaction mixture was then evaporated to dryness and the resulting light-brown sticky solid purified by column chromatography eluting with 30% ethyl acetate/hexane (50%, Rf = 0. 34). 1H NMR No. (PPM, CDCL3) 9.88 (br s, 1H, NH), 9.50 (s, 1H, CHO), 7.54 (m, 1H,, thiophene-H), 6.93 (m, 2H, thiophene-H and pyrrole-H), 6.20 (m, 1H, pyrrole-H), 4.29 (s, 2H, CH2) ; MS (EFF) 7NLZ 385 (M+, 100%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; sodium hydroxide; In methanol; dichloromethane; N,N-dimethyl-formamide; | Example 1 Preparation of 5-(pentafluorobenzoylamino)fluorescein (1) and 5-(benzoylamino)fluorescein (2): 5-Aminofluorescein (2 g, 5.8 mmol) is dissolved in 20 mL of anhydrous N,N-dimethylformamide (DMF) that contains anhydrous pyridine (0.94 mL, 11.6 mmol). To the solution is dropwise added 20 mL of an anhydrous dichloromethane solution of pentafluorobenzoyl chloride (1.3 mL, 8.7 mmol) at 0 C. under dry nitrogen protection. The resulting mixture is gradually warmed to room temperature and stirred overnight. This reaction mixture is concentrated in vacuo, and the residue is poured into water (200 mL). The precipitate thus formed is collected by filtration and washed with water. The crude solid is redissolved in methanol (20 mL). To the solution is dropwise added 1M aqueous NaOH solution (6 mL, 6 mmol), and the resulting mixture is stirred at room temperature for 2 h. This reaction solution is neutralized with 10% HCl and concentrated in vacuo. The resulting suspension is diluted with water and filtered to collect the solid, which is then washed with water and air-dried. This treatment converts the diacylated and triacylated aminofluoresceins into the desired N-monoacylated product. The crude solid is recrystallized from ethyl acetate to afford Compound 1 as brown crystals (2.1 g, yield: 67%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; | EXAMPLE 56 2-(Pentafluorobenzoyl)-3-hydroxycrotononitrile A mixture of 6.8 g. of cyanoacetone, sodium salt in 70 ml. of dry tetrahydrofuran is cooled in ice and 5.0 g. of pentafluorobenzoyl chloride diluted to 10 ml. with tetrahydrofuran is added dropwise. The reaction is stirred overnight and then the solvent is evaporated. The residue is acidified and extracted into chloroform. This chloroform phase is then extracted with aqueous sodium bicarbonate which in turn is acidified and the colorless precipitate is again extracted with chloroform. Upon evaporation of the solvent, a yellow semi-solid results which is recrystallized from ethyl ether (-78 C.) to afford off-white crystals, m.p. 62-63 C. Similarly prepared is 2-(2-chloro-6-fluorobenzoyl)-3-hydroxycrotononitrile. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With triethylamine; In chloroform; | EXAMPLES; Synthesis of crosslinkers:; Synthesis of I:; 3,3'-diamino-N-methyldipropylamme (0.29 mL,1.79 mmol, Aldrich) and triethylamine (0.55 mL, 3.93 mmol, Aldrich) were dissolved in 40 mL anhydrous CHCl3 and added dropwise to perfluorobenzoyl chloride (0.54 mL, 3.93 mmol, Aldrich) in another 40ml anhydrous CHCl3. The white precipitate of triethylammonium chloride by-product was filtered off, the filtrate washed with 3x25 mL of half-saturated NaCl solution, then dried with MgSO4, and evaporated to give N-methyl-N,N-dipropylene bis(pentafiuorobenzamide) as colorless liquid (yield, 75%). This was then dissolved (777 mg, 1.34 mmol) in 3.2 mL acetone and reacted with 10% excess sodium azide (192 mg, 2.95 mmol) dissolved in 1.5 mL water and 3 mL acetone, under reflux for 5-8hours. Excess acetone was added, the white precipitate of NaF was filtered off, and the yellow filtrate washed with 3x25 mL of half saturated NaCl solution, dried with MgSO4, and evaporated to give N-methyl-LambdaxiJV-dipropylene bis(4-azido-2,3,5,6-tetrafluorobenzamide) as a pale yellow solid (yield, 65%). This was then dissolved (505 mg, 0.87 mmol) in 10 mL anhydrous CHCl3, and reacted with excess iodomethane (5 mL, 80.3 mmol) overnight at room temperature. The fine pale yellow precipitate was filtered off and recrystallized twice in water to give N,N-dimethyl-izetaN-dipropylene bis(4-azido-2,3,5,6- tetrafluorobenzamide) ammonium iodide (I) as pale yellow crystals (yield, 55%). 1H NuMR (ppm, MeOD) = 4.56 (s), 3.50 (t, J=6.6Hz, 2H), 3.42 (m, 2H), 3.15 (s, 3H), 2.12 (m, 2H). 19F NuMR (ppm, MeOD) = -68.35 (d, J=25Hz), -76.97 (d, J=24Hz). FTIR (cm" l) = 3300 (NH), 3078 (NH), 3032 (NH), 2968 (CH3), 2942 (CH2), 2885 (CH2), 2157- 2129 (N3), 1658 (CO), 1549 (CONH), 1486 (N3), 1437 (CH2), 1407 (CH3, CH2), 1338 (N3), 1278 (N3), 1024, 1000, 989. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In pyridine; dichloromethane at 20℃; Combinatorial reaction / High throughput screening (HTS); | 3 To about 295 mg (1.0 mmoles) of (S)-3- (2,5-dimethocyphenacyl) -5- hydroxymethyl-2-oxazolidinone in dry CH2Cl2 (8 mL CH2Cl2), 1.0 equiv. (1.1 mmoles) of pyridine was added and the reaction mixture stirred at room temperature. To this reaction mixture was added 1.0 equiv. of a mixture of ten different acetyl chlorides. The reaction was stirred overnight at room temperature. Afterwards, TLC of an aliquot indicated that complete conversion of the (S)-3- (2,5-dimethocyphenacyl) -5- hydroxymethyl-2-oxazolidinone to (S)-3- (2,5- dimethocyphenacyl)-5- (substituted methyl) -2- oxazolidinone had occurred. Therefore, about 3 mL of 20% NH4Cl was added to the reaction mixture and the organic layer removed and saved. The aqueous layer was extracted two times with 40 mL aliquots of CH2Cl2. The CH2Cl2 extracts were combined with the saved organic layer and the mixture dried with 2.5 g anhydrous Na2SO4. The mixture was then concentrated in vacuo to provide a crude product. The crude product was analyzed by 1H-NMR, 13C NMR, HPLC, and TLC using a EtOAc: hexane (2: 1) solvent system. An HPLC profile of the (S)-3- (2,5- dimethocyphenacyl)-5- (substituted methyl) -2- oxazolidinone products made is shown in Figure 3. The products represented by the peaks in the HPLC are shown in Figure 4. This example illustrates the principle of the present invention. As shown by this example, providing n=10 acetyl halides in a single reaction produces 10 (S)-3- (2,5-dimethocyphenacyl) -5- (substituted methyl) -2-oxazolidinone products. If n=10 aryl bromides had been used as well to arylate the N at the 3-position, the process would have generated 100 (S)-3- (substituted)-5- (substituted methyl) -2-oxazolidinone products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63.8% | 7 N-(2-methvlcvclohexvl)-2,3,4,5,6-pentafluoro-benzamide EXAMPLE 7 N-(2-methvlcvclohexvl)-2,3,4,5,6-pentafluoro-benzamide The title compound was prepared in a similar manner to Example 5 using cyclohexyl amine and 2,3,4,5,6-pentafluorobenzoyl chloride. A white solid was obtained in a yield of 63.8%. 1H NMR (CDCl3) δ 1.17-1.29 (m, 3H), 1.38-1.47 (m, 2H), 1.63-1.67 (m, 1H), 1.73-1.77 (m, 2H), 2.01-2.05 (m, 2H), 3.98 (m, 1H), 5.83 (br.s, 1H), MS (294.1, M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With triethylamine In tetrahydrofuran at -78 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86.0% | With triethylamine; In dichloromethane; at 10 - 20℃; | 4,4'-Hydoxydiphenyl ether 5.00 g (24.75 mmol), triethylamine 5.01 g (49.50 mmol), and dichloromethane 100 g were charged into a flask and kept at 10 C. in a water bath. Pentafluorobenzoyl chloride 11.41 g (49.50 mmol) and dichloromethane 20 g were added to a dropping funnel and dropwise added slowly to the flask.On completion of the dropping addition, the water bath was taken out, the mixture was reacted at a room temperature for 3 hours. After the reaction, the mixture was added to water and the produced solid was recovered and recrystallized with methanol to obtain BPDES. The yield was 86.0% and the melting point Tm was 130 C. The charts of 1H-NMR and 19F-NMR measurement of the obtained BPDES are shown in FIG. 3 and FIG. 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | Stage #1: dithieno[3,2-b;2',3'-d]thiophene With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 1h; Inert atmosphere; Stage #2: pentafluorobenzoylchloride In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; | |
36% | Stage #1: dithieno[3,2-b;2',3'-d]thiophene With n-butyllithium Stage #2: pentafluorobenzoylchloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | With aluminum (III) chloride In carbon disulfide for 168h; Inert atmosphere; Reflux; | |
With aluminum (III) chloride In dichloromethane at 35℃; for 168h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Synthesis of the N-(4-isopropoxy-3-vinylphenyl)pentafluorobenzamide compound 6c Using the general procedure for obtaining amides from 4-isopropoxy-3-vinylaniline 5 (39 mg; 0.22 mmol) and with pentafluorobenzoyl chloride (38 μL), pentafluorobenzamide is obtained after chromatography on silica gel (eluent: CH2Cl2/EP (9:1)) in the form of a pink solid (75 mg, 92%). Rf (CH2Cl2/EP (9:1))=0.71 NMR 1H (400 MHz, CDCl3) δ (ppm): 7.70 (s, 1H, NH); 7.59 (d, 1H, 4J=2.7 Hz, H7); 7.46 (dd, 1H, 3J=8.9 Hz, 4J=2.7 Hz, H5); 7.02 (dd, 1H, 3Jcis=11.2 Hz, 3Jtrans=17.8 Hz, H9); 6.87 (d, 1H, 3J=8.9 Hz, H4); 5.73 (dd, 1H, 2Jgem=1.3 Hz, 3Jtrans=17.9 Hz, H10a); 5.27 (dd, 1H, 2Jgem=1.3 Hz, 3Jcis=11.2 Hz, Hp); 4.52 (sept., 1H, 3J=6.1 Hz, H2); 1.35 (d, 6H, 3J=6.1 Hz, H1) NMR 19F (376.5 MHz, CDCl3) δ (ppm): -140.5 (d, 2F, 3JF·F=16 Hz, F72); -150.5 (t, 1F, 3JF·F=20 Hz, F14); -160.1 (dt, 2F, 3JF·F=20 Hz, 3JF·F=15 Hz, F13) NMR 13C (100 MHz, CDCl3) δ (ppm): 155.2 (C=O); 152.9 (C3); 145.5-142.9-138.9-136.4 (C12, C13, C14); 131.1 (C9); 129.6 (C8); 128.6 (C6); 121.2 (C7); 119.0 (C5); 115.1 (C4); 114.8 (C10); 111.6 (C11); 71.4 (C2); 22.1 (Cl) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | Stage #1: dithieno[3,2-b;2',3'-d]thiophene With n-butyllithium Stage #2: pentafluorobenzoylchloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With boron trifluoride diethyl etherate; 2,3-dicyano-5,6-dichloro-p-benzoquinone In chloroform | 1 Corrole formation may be a minor side-product under Lindsey conditions. The synthesis of the A3 corrole tris(pentafluorophenyl)corrole (11) was undertaken as an exemplar; the synthetic strategy is shown in FIG. 2. Large scale (75 mmol) synthesis of 11 was performed by condensation of commercially available pyrrole, pentafluorobenzaldehyde and paraformaldehyde under Lindsey conditions. Thin layer chromatography (TLC) and Matrix-Assisted Laser Desorption/Ionization Time of Flight (MALDI-TOF) analysis of the crude reaction mixture revealed 11 as a major product. Trace amounts of porphyrins 12 and 13 were also observed as side products. The desired product 11 was isolated by flash column chromatography in 42% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With triethylamine; In diethyl ether; at -8 - 0℃;Inert atmosphere; | To a cooled (-8 C) solution of 8 (407 mg, 1.34 mmol)and Et3N (0.18 mL, 1.28 mmol) in Et2O (6.7 mL) was added 2,3,4,5,6-<strong>[2251-50-5]pentafluorobenzoylchloride</strong> (0.18 mL, 1.28 mmol) drop-wise. The reaction mixture was stirred at 0 C for 3h andquenched with aqueous 1 N HCl (2 mL). The aqueous layer was extracted with Et2O (3 x 5 mL).The combined organic layers were washed sequentially with H2O (5 mL), saturated aqueousNaHCO3 (5 mL) and brine (5 mL), dried (MgSO4), filtered (Celite) and concentrated in vacuo.The crude oil was purified by flash chromatography (5:95 EtOAc/hexanes to 10:90EtOAc/hexanes) to afford 9 as a white foam/clear oil (610 mg, 96%): 1H NMR (500 MHz,CDCl3) delta 8.31 (s, 1H), 6.17 - 6.06 (m, 1H), 5.19 (d, J = 5.2 Hz, 1H), 4.30 (ddd, J = 17.4, 3.4, 1.8Hz, 1H), 4.20 (dd, J = 17.4, 1.6 Hz, 1H), 3.81 - 3.71 (m, 3H), 3.48 (q, J = 7.0 Hz, 1H), 1.21 (t, J= 7.0 Hz, 1H), 0.88 (s, 9H), 0.07 (s, 6H); 13C NMR (126 MHz, CDCl3) delta 155.4, 133.6, 121.8,76.5, 67.3, 66.0, 61.7, 25.9, 18.3, 15.4, -5.4, -5.5; IR (thin film) 3240, 2950, 2931, 2858, 1780,1759, 1675, 1504, 1329, 1254, 1184, 1097, 1003, 839; HRMS (CI) m / z calcd forC20H24F5NO6Si (M + Na)+ 520.1191, found 520.1188; [alpha]24D -159.8 (c 0.55, CHCl3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | General procedure: To a suspension of sodium hydride (55% in oil, 173 mg, 3.97 mmol, washed with hexane) in tetrahydrofuran, a solution of 7 (910 mg, 3.97 mmol) in tetrahydrofuran was added. The mixture was stirred for 15 min, then benzoyl chloride (0.67 mL, 5.70 mmol) was added. The resulting mixture was heated at 60 C for 18 h and extracted with AcOEt. The organic solution was washed with brine and dried over MgSO4. Volatiles were removed under reduced pressure, and the residue was flash-chromatographed (AcOEt/n-hexane 1:8) to afford 1.23 g (93%) of amide 4b. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With pyridine In benzene at 20℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51.9% | Step 2. 2,7-Bis-(thiophene-2-yl)-benzo[2,l-¾:3,4-¾]dithiazole-4,5-bis(ethyleneoxolane) (1.5 mmol, 0.709 g) was dissolved in anhydrous THF under nitrogen atmosphere and yellow solution was cooled in acetone/dry ice bath. n-Butyllithium (2.85 M in hexanes, 3.0 mmol, 1.05 mL) was added dropwise and yellow solution became lighter in color and then precipitate formed. The reaction mixture was stirred for 1 h and pentafluorobenzoyl chloride (3 eq., 4.5 mmol, 1.04 g) was added quickly to the suspension. Yellow mixture became orange-reddish, and after stirring for 40 minutes bright orange-red solution was allowed to warm to room temperature. After 10 minutes of stirring precipitate was observed. Mixture was treated with aqueous NH C1 and dichloromethane was added. Organic phase was removed and dried over MgS04. The drying agent was filtered off and the organic solvents were removed by rotary evaporation. Crude product was purified by column chromatography (150 mL of silica gel, dichloromethane as eluant). First fractions with a product slightly contaminated by mono-substituted material were combined separately, the solvent was removed by rotary evaporation and red solid was obtained (Pdt - 259-a, 0.45 g, -35% yield). Fractions with pure product were combined separately, the solvent was removed by rotary evaporation and dark red solid was obtained (Pdt - 259-b, 0.67 g, 51.9% yield). 1H NMR (CDCI3, 400 MHz): £7.50 (s, 2H), 7.42 (d, J= 4.1 Hz, 2H), 7.24 (d, J Hz, 2H), 4.23 (m, 4H), 3.76 (m, 4H); DEPT-135 (CDC13, 100 MHz): delta 136.94 (CH), 124.9(3) (CH), 124.8(6) (CH), 61.7 (CH2). HRMS (EI) calculated for C36Hi4Fi0O6S4 859.9514; found 859.9509. Anal. Calc. for C36Hi4Fi0O6S4: C, 50.23; H, 1.64. Found: C, 50.14; H, 1.46. | |
51.9% | Step 2. 2,7-Bis-(thiophene-2-yl)-benzo[2,l-¾:3,4-¾]dithiazole-4,5-bis(ethyleneoxolane) (1.5 mmol, 0.709 g) was dissolved in anhydrous THF under nitrogen atmosphere and yellow solution was cooled in acetone/dry ice bath. n-Butyllithium (2.85 M in hexanes, 3.0 mmol, 1.05 mL) was added dropwise and yellow solution became lighter in color and then precipitate formed. The reaction mixture was stirred for 1 h and pentafluorobenzoyl chloride (3 eq., 4.5 mmol, 1.04 g) was added quickly to the suspension. Yellow mixture became orange-reddish, and after stirring for 40 minutes bright orange-red solution was allowed to warm to room temperature. After 10 minutes of stirring precipitate was observed. Mixture was treated with aqueous NH C1 and dichloromethane was added. Organic phase was removed and dried over MgS04. The drying agent was filtered off and the organic solvents were removed by rotary evaporation. Crude product was purified by column chromatography (150 mL of silica gel, dichloromethane as eluant). First fractions with a product slightly contaminated by mono-substituted material were combined separately, the solvent was removed by rotary evaporation and red solid was obtained (Pdt - 259-a, 0.45 g, -35% yield). Fractions with pure product were combined separately, the solvent was removed by rotary evaporation and dark red solid was obtained (Pdt - 259-b, 0.67 g, 51.9% yield). 1H NMR (CDCI3, 400 MHz): £7.50 (s, 2H), 7.42 (d, J= 4.1 Hz, 2H), 7.24 (d, J Hz, 2H), 4.23 (m, 4H), 3.76 (m, 4H); DEPT-135 (CDC13, 100 MHz): delta 136.94 (CH), 124.9(3) (CH), 124.8(6) (CH), 61.7 (CH2). HRMS (EI) calculated for C36Hi4Fi0O6S4 859.9514; found 859.9509. Anal. Calc. for C36Hi4Fi0O6S4: C, 50.23; H, 1.64. Found: C, 50.14; H, 1.46. | |
Step 2. 2,7-Bis-(thiophene-2-yl)-benzo[2,l-¾:3,4-¾]dithiazole-4,5-bis(ethyleneoxolane) (1.5 mmol, 0.709 g) was dissolved in anhydrous THF under nitrogen atmosphere and yellow solution was cooled in acetone/dry ice bath. n-Butyllithium (2.85 M in hexanes, 3.0 mmol, 1.05 mL) was added dropwise and yellow solution became lighter in color and then precipitate formed. The reaction mixture was stirred for 1 h and pentafluorobenzoyl chloride (3 eq., 4.5 mmol, 1.04 g) was added quickly to the suspension. Yellow mixture became orange-reddish, and after stirring for 40 minutes bright orange-red solution was allowed to warm to room temperature. After 10 minutes of stirring precipitate was observed. Mixture was treated with aqueous NH C1 and dichloromethane was added. Organic phase was removed and dried over MgS04. The drying agent was filtered off and the organic solvents were removed by rotary evaporation. Crude product was purified by column chromatography (150 mL of silica gel, dichloromethane as eluant). First fractions with a product slightly contaminated by mono-substituted material were combined separately, the solvent was removed by rotary evaporation and red solid was obtained (Pdt - 259-a, 0.45 g, -35% yield). Fractions with pure product were combined separately, the solvent was removed by rotary evaporation and dark red solid was obtained (Pdt - 259-b, 0.67 g, 51.9% yield). 1H NMR (CDCI3, 400 MHz): £7.50 (s, 2H), 7.42 (d, J= 4.1 Hz, 2H), 7.24 (d, J Hz, 2H), 4.23 (m, 4H), 3.76 (m, 4H); DEPT-135 (CDC13, 100 MHz): delta 136.94 (CH), 124.9(3) (CH), 124.8(6) (CH), 61.7 (CH2). HRMS (EI) calculated for C36Hi4Fi0O6S4 859.9514; found 859.9509. Anal. Calc. for C36Hi4Fi0O6S4: C, 50.23; H, 1.64. Found: C, 50.14; H, 1.46. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | 5'-Tetrabromo-4,4'-di-n-hexyl-2,2'-bithiophene (3a) Diisopropylamine (distilled from CaH2, 90.0 mmol, 9.11 g) was dissolved in anhydrous THF (160 ml) under nitrogen atmosphere and the resulting solution was cooled (acetone/dry ice bath). n-Butyllithium (2.5 M in hexanes, 82.5 mmol, 33.0 ml) was added dropwise, the cooling bath was removed and the mixture was stirred for half an hour. This freshly prepared solution of LDA was cooled (acetone/dry ice bath) and 2,5-dibromo-3-n- hexylthiophene (75.0 mmol, 24.46 g) was added dropwise. The bright yellow reaction mixture was stirred for lh and CuCl2 (82.5 mmol, 11.09 g) was added in one portion. The mixture from yellow-orange became blue. The reaction mixture was allowed to warm slowly to room temperature overnight (without cooling bath removal). The reaction mixture was treated with water (~70 ml) and hexanes (copper salts precipitated out). The organic phase was removed, the aqueous phase was extracted with hexanes two times and the combined organic phases were dried over MgS04. The solvents were removed by rotary evaporation and the crude product was obtained as brownish oil. The crude product was dissolved in hexanes and filtered through silica gel plug (-400 ml of hexanes as eluant was used). Barely yellowish solution was collected (brown and green matter got stuck on the silica gel), the solvent was removed and the yellowish oil was dried under vacuum. Yellowish oil solidified on scratching and yellowish solid was obtained (19.74 g, 81.0%). HRMS (EI) calculated for C20H26Br4S2 645.8209; found 645.8171. 1H NMR (CDC13, 400 MHz): delta 2.64 (t, J= 7.9 Hz, 2H), 1.53 (m, 2H), 1.43-1.20 (m, 6H), 0.88 (t, J= 6.8 Hz, 3H); 13C{1H} NMR (CDC13, 100 MHz): delta 141.5, 128.5, 114.6, 111.0, 31.5, 30.3, 29.0, 28.5, 22.6, 14.1. Anal. Calc. for C20H26Br4S2: C, 36.95; H, 4.03. Found: C, 37.23; H, 4.03. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With aluminum (III) chloride; In 1,2-dichloro-ethane; at 0 - 40℃; for 6h;Inert atmosphere; | In a three-neck round-bottom flask (10 ml) fitted with a magnet, and a reflux condenser under N2 atmosphere were added 200.0 mg (5.53 x10-1 mmol) of N,N-dihexylanthracen-2-amine (2) and 2.00 ml of 1,2-dichloroethane. This mixture was conducted at a temperature of 0-40 C. Then was added a suspension containing 151.2 mg (1.13 mmol) of aluminum chloride, 263.7 mg (1.14 mmol) of pentafluorobenzoyl chloride and 2.00 ml of 1,2dichloroethane. The reaction was maintained at 0-40 C. After 6 hours of reaction, occurred in both cases by thin layer chromatography, virtually complete consumption of starting material. Was added 5.00 ml of a solution of 10% hydrochloric acid and then extracted the reaction with 50.00 ml of dichloromethane. The organic extract was washed with distilled water, dried over sodium sulfate and then concentrated under reduced pressure. The waste generated was not purified. Obtained as a solid (1e) brown paste. Yield 245.8 mg (80.0%). 1H NMR (500 MHz, CDCl3) delta = 8.21 (s, 1H), 8.16 (s, 1H), 7.84 (m, 3H), 7.30 (m, 2H), 7.16 (m, 1H), 3.33 (t, J = 7.8 x 2 Hz, 4H), 1.58 (s, 4H), 1.24 (m, 15H), 0.80 (t, J = 6.1 x 2 Hz, 6H). 13C NMR (125 MHz, CDCl3) delta = 132.6, 132.5, 130.2, 129.9, 128.1, 127.5, 126.0, 125.4, 124.1, 123.7, 117.5, 53.2, 47.8, 31.5, 31.1, 26.6, 26.4, 25.8, 22.5, 22.4, 13.9, 13.8. UV-vis (THF) lambda1 = 249 nm, epsilon1 = 6.65 x 104 L mol-1 cm-1, lambda2 = 289 nm, epsilon2= 3.84 x 104 L mol-1 cm-1, lambda3 = 434 nm, epsilon3 = 5.54 x 103 L mol-1 cm-1. IR (cm-1) 2930, 1732, 1625. (m/z): [M + H] calculated for C33H35F5NO, 556.2639, found 556.2633. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃;Cooling with ice; | General procedure: A mixture of various carboxylic acids (1.0mmol), an excess of thionyl chrolide (5mL) was refluxed for 2h and concentrated in vacuo to give corresponding acyl chloride (quant). The corresponding acyl chloride was dissolved in 2mL anhydrous DCM, then added dropwise to a solution of compound 2 (1.0mmol), DIPEA (1.2mmol) in 15mL anhydrous DCM in an ice bath. The reaction was then stirred at room temperature and monitored by TLC, after completion, the solvent was evaporated under reduced pressure. The residual solid was purified by column chromatography on silica gel with ethyl acetate - petroleum ether as eluent to afford the title compound 3a-w. White powder, yield 69%, mp 269-271 C. 1H NMR (400 MHz, DMSO-d6) delta 10.18 (s, 1H, CONH), 10.16 (s, 1H, CONH), 8.41 (q, J = 4.8 Hz, 1H, CONH), 7.96 (d, J = 8.0 Hz, 1H, Ph-H), 7.61 (d, J = 7.6 Hz, 1H, Ph-H), 7. 48-7.44 (m, 2H, Ph-H), 7.40-7.24 (m, 7H, Ph-H), 4.17 (s, 2H, CH2), 2.62 (d, J = 4.8 Hz, 3H, NHCH3). 13C NMR (100 MHz, DMSO-d6): delta 167.0, 164.1, 156.7, 145.2 (m), 142.7 (m), 140.7 (m), 138.6 (m), 137.3, 136.1 (m), 135.4, 135.2, 135.0, 133.2, 132.7, 131.3, 130.1, 129.7, 129.3, 128.9, 127.7, 126.8, 123.8, 123.7, 119.9, 112.6 (m), 38.1, 26.3. 19F NMR (376 MHz, DMSO-d6) delta -141.5 (dd, J1 = 22.2 Hz, J2 = 6.0 Hz), -152.5 (t, J = 22.2 Hz), -147.6 (td, J1 = 22.2 Hz, J2 = 6.0 Hz). HRMS (ES+) calcd for C29H19N3O3F5S79BrNa [M+Na]+: 686.0148. Found: 686.0160. Calcd for C29H19N3O3F5S81BrNa [M+Na]+: 688.0128. Found: 688.0121. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | Stage #1: 2-(bromomethyl)-3,3,3-trifluoroprop-1-ene; thiobenzhydroxamic acid With tetra-(n-butyl)ammonium iodide; triethylamine In diethyl ether at 20℃; Stage #2: pentafluorobenzoylchloride With triethylamine In diethyl ether at 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With triethylamine; In chloroform; at 70℃; for 2h; | General procedure: To the solution of 22 (0.1 mmol) in 1 ml of CHCl3, the corresponding aromatic acyl chlorides (49-55, 0.15 mmol) or sulfonyl chloride (56, 0.15 mmol) were added, followed by 3 equivalents of TEA. The resulting mixture was heated to70C and maintained for 2h, monitored by TLC (nhexane/ethyl acetate = 1:1). The precipitated target compounds were filtered off, washed with CHCl3 and dried over vacuo. For Characterization Data of Compounds 57-64, see Supporting Information. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With triethylamine; In dichloromethane; at 20℃; for 2h;Inert atmosphere; Cooling with ice; | General procedure: To the ice-cold solution of 2 (10 mmol) and Et3N (20 mmol) in dry CH2Cl2 (10 mL), alkyl/aryl/heteroaryl acid chloride (12 mmol) was added slowly under N2 atmosphere. The ice bath was removed and the reaction was allowed to proceed at ambient temperature for 2 h. The reaction mixture was poured onto crushed ice and extracted with CH2Cl2 (3 x 25 mL). The combined organic extract was washed with brine (20 mL), dried over sodium sulfate and evaporated under reduced pressure to afford carbohydrazide derivatives 3-17, which were purified through flash column chromatography using EtOAc/hexanes as mobile phase. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | A suspension of a mixture of Ca(OH)2 (1.43 g, 19.3 mmol) and Ba(OH)2 (0.82 g, 4.8 mmol) in THF (50 mL) was added to a solution of 1-phenyl-3-methylpyrazol-5-one (1.68 g, 9.6 mmol) in THF (50 mL). The reaction mixture was stirred at 70C for 1 h and cooled to room temperature; then <strong>[2251-50-5]2,3,4,5,6-pentafluorobenzoyl chloride</strong> (2.22 g, 9.6 mmol) was added over a period of 1 min. The mixture was stirred at 80C for 3 h, cooled to room temperature, and treated with 3 M HCl (350 mL). The precipitate was filtered off, washed with water to neutral reaction, and crystallized from a C2H5OH-H2O-CHCl3 mixture (2 : 2 : 1). HL1 wasformed as colorless crystals in a yield of 3.02 g (85%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85 %Spectr. | In tetrahydrofuran at 23℃; for 0.2h; Glovebox; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With potassium carbonate; In acetone; at 20℃; for 24h; | General procedure: 2 mmol of either amidoxime 1 [30] or 2 [26] were dissolved in acetone (200 mL) in a round-bottomed flask; then, K2CO3 (0.35 g; 2.5 mmol) and the corresponding aroyl chloride (2.5 mmol), were added to the reaction mixture and stirred for 24 h at room temperature. The solvent was removed under vacuum and the residue treated with water and refluxed for 30 min 1,2,4-Oxadiazoles products were obtained by filtration and further purified by chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With dmap; potassium carbonate; In acetonitrile; at 20℃; for 6h; | 1-Aminopyridinium iodide(0.889 g, 4.00 mmol)Of distilled acetonitrile solution(40 mL)Was cooled to 0 C. under nitrogen.4-dimethylaminopyridine(DMAP)(50.4 mg, 0.4114 mmol),Potassium carbonate(1.64 g, 11.8 mmol)And pentafluorobenzoyl chloride(0.955 g, 4.14 mmol)Was added and the reaction mixture was stirred at room temperature for 6 hours.The suspension was filtered,The acetonitrile was removed and concentrated in vacuo.The residue was suspended in dichloromethane,And filtered to remove inorganic impurities.The filtrate was concentrated in vacuo,The crude product was purified by silica gel flash column chromatographyPurification by fee (CH 2 Cl 2 / MeOH = 20/1)1- (pentafluorobenzoylamino) -pyridinium ylide as a white solid(0.715 g, 2.48 mmol, 62% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With potassium carbonate; In acetonitrile; at 20℃; for 3h;Inert atmosphere; | General procedure: A mixture of the methylester 6a-d, 7 (0.216 mmol), K2CO3 (0.324 mmol) in CH3CN(25mL), the appropriate acyl chloride (0.26 mmol) wasadded under nitrogen atmosphere, stirred at rt for 3 h,the solvent was evaporated in vacuum. The residue was diluted with water. The whole was extracted with AcOEt for 3 times. The combined organic layer was washed with water, sat.brine, dried over Na2SO4. The crude mixture was purifiedby (n-hexane/AcOEt = 8:1) to afford 8a-z, 10-13. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With triethylamine; In dichloromethane; at 0 - 20℃; | At 0 C the solution of HOCH2CRCH (1.65 mL, 28.20 mmol), Et3N (3.45 mL, 24.76 mmol) in CH2Cl2 (10 mL) was added dropwise to the solution of C6F5COCl (5.42 g, 23.51 mmol) in CH2Cl2 (30 mL). Reaction mixture was warmed to room temperature and stirred overnight. Then water (30 mL) was added, organic phase was separated, aq. phase was extracted with CH2Cl2 (220 mL). Combined organic phases were washed with water (220 mL), dried (MgSO4) and evaporated under reduced pressure. After recrystallization from methanol C6F5C(O)OCH2CRCH (3.77 g, 64%) was isolated as a white low melting substance, m.p. 36 C. 1H NMR (400.130 MHz, CDCl3): delta= 4.95 (d, 4JH,H = 2.4 Hz, 2H, OCH2), 2.56 (t, 4JH,H = 2.4 Hz, 1H, RCH) ppm. 13C NMR (100.613 MHz, CDCl3): delta= 158.3(CO), 146.96-146.79 m, 144.33-144.20 m, 142.54-141.94 m, 139.16-138.83 m, 136.51-136.30 m, 107.38-107.16 m (aromatic carbons), 77.8 (RC), 76.1 (RCH) ppm. One aromatic carbon did not found. 19F NMR (376.498 MHz, CDCl3): delta=137.45 to 137.57 (m, 2F), 147.58 to 147.71 (m, 1F), 160.13 to 160.29 (m, 2F) ppm. Elemental analysis calc. for C10H3F5O2 (Mw 250.1216): C48.02, H 1.21. Found: C 48.37, H 1.41. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With dmap; triethylamine In dichloromethane at 0 - 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With triethylamine; In tetrahydrofuran; at 20℃; for 24h;Inert atmosphere; | A stirred solution of 2,2-(ethylenedioxy)-bis-(ethylamine) (0.148 g, 1 mmol) and Et3N (0.202 g, 2 mmol) in THF (4 mL) was treated dropwise with pentafluorobenzoyl chloride (0.46 g, 2 mmol) in THF (2 mL) and the reaction mixture maintained at room temperature under N2 for 24 h. The solvent was evaporated and water (10 mL) added to the residue. A yellow orange solid precipitated, and was filtered, (0.5 g). Recrystallisation from CH2Cl2 and light petroleum gave 10 as shiny white crystals (0.38 g, 71%); m.p. 128 - 129 C; vmax/cm-1 (film), 3279 (N-H), 2872, 1658 (C=O), 1501, 1135, 1119, 992, 731; deltaH (400 MHz, CDCl3) 6.55 (2H, s, NH), 3.70-3.66 (8H, m), 2.87 (4H, m); deltaC (100 MHz, CDCl3) 157.6, 144.2 (dd, 1JCF 255, 2JCF 12), 142.3 (dd, 1JCF 260, 2JCF 25), 137.5 (dd, 1JCF 230, 2JCF 32), 111.5 (t, 2JCF 30), 70.8, 69.8, 40.1; deltaF (376 MHz, CDCl3) 21.2-21.1 (4F, AA'), 11.26 (2F, t, 3JFF 20.3), 1.74-1.90 (4F, BB'); HRMS (ESI) found m/z 537.0867 (MH+), C20H15F10N2O4 requires 537.0867; Anal. (%) calcd for C20H14F10N2O4 (536): C, 44.79; H, 2.63; N, 5.22; found: C, 44.78; H, 2.44; N, 5.25. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | Several crystals of iodine were added to magnesium turnings (1.2 g, 50 mmol), heated until vigorous sublimation of iodine commences, then MeOH (10 ml, 250 mmol) and a few drops of CCl4 were added. Then acetylacetone (5.0 g 50 mmol) in dry PhMe (25 ml) were added dropwise. The mixture was stirred at reflux temperature until complete dissolution of magnesium turnings and cooled to 20C. A solution of pentafluorobenzoyl chloride (1a) (11.5 g, 50 mmol) in dry PhMe (20 ml) was added dropwise with stirring. The reaction mixture was heated under reflux with vigorous stirring for 6 h. Upon completion of the reaction, the mixture was poured onto ice-cold 10% (wt) H2SO4 (50 ml). Toluene layer was separated and dried over Na2SO4. PhMe was removed under reduced pressure, and the residue recrystallized. Yield 11.0 g (80%), white powder, mp 126C (EtOH). IR spectrum, nu, cm-1: 1717 (MeC=O), 1647 (C=O), 1522, 1494, 1404 (C=C, C-H), 1030, 1004, 969 (CF). 1H NMR spectrum (DMSO-d6), delta, ppm (J, Hz): 2.42 (3H, s, CH3); 2.47 (3H, s, CH3=O). 13C NMR spectrum (DMSO-d6), delta, ppm (J, Hz): 19.2 (s, CH3); 31.9 (s, CH3=O); 76.7-77.3 (m, C-3); 110.7-110.9 (m, C-4a); 136.9 (dddd, J = 1.3, J = 6.0, J = 12.5, J = 256.8, C-8); 138.0 (dddd, J = 1.0, J = 13.0, J = 15.5, J = 254.8, C-6); 140.6-140.8 (m, C-8a);142.7-146.0 (m, C-5, 7); 167.7 (s, C-2); 172.2 (br. s, C-4), 198.7 (s, CH3=O). 19F NMR spectrum (DMSO-d6), delta, ppm (J, Hz): 0.9-1.1 (1F, m); 3.8 (1F, dd, J = 12.2, J = 21.4), 14.2-14.3 (1F, m); 18.3 (1F, dddd, J = 2.0, J = 6.6, J = 12.1, J = 18.8). Mass spectrum, m/z (Irel, %): 274 [M]+ (100), 259 [M-CH3]+ (92). Found, %: C 52.33; H 2.22; F 27.67. C12H6F4O3. Calculated, %: C 52.57; H 2.21; F 27.72. | |
General procedure: In a three-necked flask, equipped with a reflux condenser and a drop funnel, several iodine crystals and 1.2 g (50 mmol) of magnesium turnings were added, heated with stirring until the vigorous sublimation of iodine, then 10 ml (250 mmol) of MeOH and a few drops of CCl4 were added. While vigorous hydrogen evoluation, 25 ml of absolute toluene was added to the mixture. Then 50 mmol of corresponding diketone 2, 3 was added in portions while stirring. The mixture was refluxed until the magnesium turnings were completely dissolved, and then cooled to room temperature. The solvent was removed in vacuo till the mass thickening, then 25 ml of absolute toluene was added. Polyfluorobenzoyl chloride 1a,b (50 mmol) in 20 ml of absolute toluene was added to the mixture dropwise with stirring at the room temperature. The mixture was stirred for 6 h at room temperature, then poured into 150 ml 0.5M HCl. An organic layer was separated and dried over anhydrous Mg2SO4. To the mixture, separated from Mg2SO4, 0.6 g (5 mmol) of DIPEA was added, and then refluxed for 2 h. The solvent was removed in vacuo, and the residue was crystallized fractionally from toluene. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With potassium carbonate; In acetonitrile; at 20℃; for 3h;Inert atmosphere; | General procedure: A mixture of 3 (0.216 mmol), K2CO3 (0.324 mmol) in acetonitrile(25 mL), and the appropriate acyl chloride (0.26 mmol) was addedunder nitrogen atmosphere, stirred at rt for 3 h, the solvent wasevaporated in vacuum. The residue was diluted with water. Thewhole mixture was extracted with AcOEt for three times. Thecombined organic layer was washed with water, sat. brine, anddried over Na2SO4. The crude product was purified by columnchromatography using petroleum ether/AcOEt (2/1-5/1, v/v) aseluent to afford 3a-s. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | A solution of 11beta-hydroxysteroid 13 (190mg, 0.385mmol) in anhydrous THF (5mL) under argon was cooled with stirring to-78C, and butyllithium (0.29mL, 1.6M in hexane) was added dropwise. The reaction mixture was stirred for additional 10min, and pentafluorobenzoyl chloride (0.067mL, 0.46mmol) was added dropwise, followed by N,N-diisopropylethylamine (0.1mL, 0.57mmol). After an overnight stirring, a usual work-up and chromatography (hexane - ethyl acetate 24:1), the pentafluorobenzoyl derivative 14 was crystallized from methanol (190mg, 72%). 1H NMR (CDCl3): delta 5.71 (q, J=2.5Hz, 1H, 11alpha-CH), 4.04-3.80 (m, 5H, OCH2CH2O+3beta-CH), 2.47 (dd, J=14.9, 1.8Hz, 1H), 1.86-1.65 (m, 6H), 1.62-1.45 (m, 6H), 1.45-1.32 (m, 2H), 1.28 (s, 3H, CH3), 1.27-1.05 (m, ?8H), 1.02 (s, 3H, CH3), 0.90 (s, 9H, tert-Bu), 0.87 (s, 3H, CH3), 0.81 (d, J=7.0, 3.0Hz), 0.03 (s, 6H, Si-CH3). 13C NMR (CDCl3): delta 158.7, 144.5 (dm, J?255.8Hz), 142.7 (dm, J?258.7Hz), 137.6 (dm, J?250.7Hz), 111.6, 74.2, 66.5, 65.0, 63.2, 58.5, 57.4, 57.0, 44.5, 41.0, 40.2, 36.2, 35.8, 32.2, 32.1, 31.4, 29.7, 29.2, 27.8, 25.9, 24.5, 23.6, 22.7, 18.1, 14.8, 13.9,-4.9. 19F NMR (CDCl3): delta-138.6 (m, 2F, o-CF),-149.9 (tt, J=17.5, 3.3Hz, 1F, p-CF),-160.2 (m, 2F, m-CF). HR MS: predicted for C36H52O5F5Si [M+H]+: 687.3504; found: 687.3530. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With triethylamine In dichloromethane at 0 - 20℃; for 13h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With triethylamine; In tetrahydrofuran; at 0 - 20℃; for 24h; | Ylide 42 was prepared by slowly adding triethylamine (3.0 g, 29.6 mmol) to a suspension of cyanomethyltriphenylphosphonium chloride 90 (5.0 g, 14.8 mmol) in THF (60 mL) stirred at 0 C. After 20 min, pentafluorobenzoyl chloride (3.41 g, 14.8 mmol) was added dropwise and the resulting mixture was allowed to warm to RT and stirred for 24 h. It was the added to water and the resulting solid was filtered off, washed with water and dried. Recrystallisation from ethyl acetate gave the pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | General procedure: Ylides 38, 39, 40, 41, 44 and 45 were prepared using the method shown in Scheme 2 as follows. A suspension of methyltriphenylphosphonium bromide (12.0g, 33.6mmol) in dry THF (70mL) was stirred under nitrogen while n-butyllithium in hexanes (2.5M, 13.5mL, 33.7mmol) was added slowly at RT. After 20min either hexafluorobenzene or octafluorotoluene (16.8mmol) in dry THF (10mL) was added and the mixture was stirred for 1 h after which time a deep red precipitate had formed. To this mixture a solution of pentafluorobenzoyl chloride, trifluoroacetic anhydride, or methyl or ethyl oxalyl chloride (8.4 mmol) in dry THF (5mL) was added and the mixture was stirred overnight before being added to water. Extraction with diethyl ether (3×50mL), drying and evaporation gave the products, which were recrystallised from ethyl acetate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With N-ethyl-N,N-diisopropylamine; In Dichlorofluoromethane; at 0℃; for 0.25h;Inert atmosphere; | To a stirred solution of benzyl (R)-2-(benzyloxy)-4-(N-(4-cyclohexylbenzyl)pyirolidine-2-carboxamido)benzoate (203mg, 0.337 mmol) in DCM (5mL) at 0 C under nitrogen was added DIPEA (0.088 mL, 0.50 mmol) followed by 2,3,4,5, 6-pentafluorbenzoyl chloride (0.058 ml, 0.40 mmol). The resulting reaction mixture was stirred at 0 C for 15 min before addition of saturated aqueous ammonium chloride. The crude reaction mixture was poured onto water and extracted with DCM (3X). The combined organic extracts were dried over anhydrous sodium sulfate, concentrated under reduced pressure and the resulting residue purified by flash chromatography (10-25% EtOAc/hexanes eluent) to provide benzyl (R)-2-(benzyloxy)-4-(N-(4-cyclohexylbenzyl)-l-(peifluorobenzoyl)pyiTolidine-2-carboxamid o)benzoate (226 mg, 84% yield). MS (ESI) m/z 797.2[M + H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With triethylamine; In diethyl ether; at 0℃; for 2.5h;Reflux; | General procedure: Benzoyl chloride (10.0 mmol) in Et2O (10 mL) was added dropwise to a solution of <strong>[421-85-2]trifluoromethanesulfonamide</strong> (1.5 g,10.0 mmol) and triethylamine (3.5 mL, 25 mmol) in Et2O (30 mL) at 0 C over 10 min. The mixture was stirred for30 min and then heated to reflux for 2 h. The reaction was filtered and the solvent was removed from the filtrate. The crude product was mixed with 50% H2SO4 (aq, 50 mL) and the mixture stirred for 30 min. The precipitate was isolated and dried overnight. The product was purified by recrystallization from toluene. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | Stage #1: 2,3,4,5-tetrahydro-1H-1-benzo[b]azepin-2-one With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: pentafluorobenzoylchloride In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | In dichloromethane; at 22℃; for 0.5h; | Piperidine (148 muIota_, 1 .5 mmol) was added to a solution of (0326) <strong>[2251-50-5]pentafluorobenzoylchloride</strong> (72 muIota_, 0.5 mmol) in DCM (5 mL),. The (0327) reaction was stirred at 22 C for 30 min. The solvent was evaporated (0328) and the crude residue was purified by column chromatography (EtOAc: pentane / 10:90) to afford the product 2b as white solid (132 mg, 95 %); 1H NMR (500 MHz, DMSO-de) delta 3.68 - 3.59 (m, 2H), 3.31 - 3.25 (m, 2H), 1 .67 - 1 .60 (m, 2H), 1 .56 (td, J = 6.8, 6.3, 4.4 Hz, 2H), 1 .50 - 1 .42 (m, 2H); 13C NMR (126 MHz, DMSO) delta 155.56, 143.02, 142.06, 141 .17, 141 .07, 140.99, 140.17, 140.06, 138.38, 138.26, 138.17, 138.13, 136.38, 136.27, 1 1 1.37, 1 1 1 .19, 1 1 1 .02, 47.19, 42.42, 26.21 , 25.21 , 23.64; 19F NMR (470 MHz, DMSO-d6) delta -143.15 (d, J = 18.0 Hz), -154.05 (t, J = 21 .3 Hz), -160.81 (t, J = 21 .3 Hz); MS (ESI+) m/z calcd. For Ci2HnF5NO+ [M+H] + 280.0755, found 280.0762. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.7% | With triethylamine; In dichloromethane; at 0 - 20℃; | General procedure: General procedure for preparation of 5a-s, 6a-e: To a solution of 4 (0.15 g, 0.47 mmol.) and Et3N (0.08 mL, 0.58 mmol) in DCM (10 mL) at 0 C, acyl chloride 7 (0.56 mmol) was added dropwise. The reaction was gradually warmed to room temperature, the termination of the reaction was measured by TLC, then quenched with water and extracted into DCM (3×10 mL). The organic phase was washed saturated aqueous sodium bicarbonate and brine, dried over sodium sulfate and the solvent was removed under reduced pressure. The crude residue was purified by silica flash column chromatography afforded compound 5a-s, 6a-e. |
Tags: 2251-50-5 synthesis path| 2251-50-5 SDS| 2251-50-5 COA| 2251-50-5 purity| 2251-50-5 application| 2251-50-5 NMR| 2251-50-5 COA| 2251-50-5 structure
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