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CAS No. : | 50868-68-3 | MDL No. : | MFCD03002751 |
Formula : | C7H5BrO2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | N/A |
M.W : | 233.08 g/mol | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501 | UN#: | N/A |
Hazard Statements: | H302-H312-H332 | Packing Group: | N/A |
GHS Pictogram: |
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* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide | ||
With water; sodium hydroxide In tetrahydrofuran; methanol at 20℃; | 5.1.22. (E)-3-(5-Bromothiophen-2-yl)acryloyl azide (17a) General procedure: A mixture of ethyl (E)-3-(5-bromothiophen-2-yl)acrylate (16a) (6.34g, 24.3 mmol) and 1 M NaOH aq. (48.6 mL, 48.6 mmol) in THF (20 mL) and MeOH (20 mL) was stirred at rt overnight. The mixture wasneutralized with 1 M HCl aq. and the solution was extracted with EtOAc.The organic layer was separated, washed with brine, dried over Na2SO4and concentrated in vacuo. This residue was used to the next reactionwithout further purification. Ethyl chloroformate (3.49 mL, 36.5 mmol)was added to a mixture of the crude product, TEA (5.09 mL, 36.5 mmol)in acetone (48 mL) at 0 C. After stirring at this temperature for 1 h, amixture of sodium azide (2.52 g, 38.8 mmol) in water (9.5 mL) wasadded dropwise to the reaction mixture. The mixture was stirred at 0 Cfor 1 h. The resulting mixture was poured into water and stirred at rt for10 min. The precipitate was collected by filteration to give the titlecompound as a pale pink solid (4.62 g, 17.9 mmol, 78%). 1H NMR (300MHz, CDCl3) δ 6.10 (1H, d, J = 15.4 Hz), 6.98-7.12 (2H, m), 7.59-7.86(1H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With piperidine; pyridine for 3h; Reflux; Inert atmosphere; | |
94% | With piperidine; pyridine for 3h; Reflux; | (E)-3-(5-Bromothiophen-2-yl)acrylic acid (5). To a solution of 5-bromothiophene- 2-carboxaldehyde (4) (10.15 g, 51.53 mmol) in pyridine (128 mL) were added malonic acid (16.25 g, 154.6 mmol) and piperidine (2.57 mL, 25.76 mmol). The reaction mixture was heated at reflux for 3 h, cooled to room temperature and concentrated to give a dark oil. The oil was diluted with TbO (30 mL), at which time a solid precipitated. The suspension was then acidified to pH 2 with 6 M HC1. The precipitate was filtered and washed with H2O (3 x 15 mL). The filter cake was dissolved in EtOAc, dried (MgSCL), filtered, and concentrated to give 5 (11.29 g, 94%) as a tan solid: NMR (300 MHz, DMSO-de) d 12.41 (brs, 1 H), 7.66 (d, J= 15.9 Hz, 1 H), 7.35 (d, J= 3.9 Hz, 1 H), 7.27 (d, J= 3.9 Hz, 1 H), 6.15 (d, J= 15.9 Hz, 1 H). Spectral data are consistent with literature properties.37 |
90.5% | Stage #1: 5-bromo-2-thiophencarboxaldehyde; malonic acid With piperidine; pyridine at 80℃; for 1h; Stage #2: at 100℃; for 12h; Stage #3: With hydrogenchloride | INTERMEDIATE 47 [ (2E)-3- (5-BROMOTHIEN-2-YL) ACRYLIC ACID] INTERMEDIATE 47 [ (2E)-3- (5-BROMOTHIEN-2-YL) ACRYLIC ACID] Malonic acid (44.40 g, 426.7 mmol) was added to a mixture [OF 5-BROMOTHIOPHENE-2-] carbaldehyde (50 g, 261.7 mmol), piperidine (2.84 mL) and pyridine (150 mL). The mixture was refluxed for 1 h at [80°C] and than at [100 °C] over night. The volatiles were evaporated and the residue was dissolved in water and acidified with hydrochloric acid (pH 2). The crude product was crystallized in ethanol. Yield: 55.24 g (90.5 %). 1H NMR (270 MHz, CH30H-d4) 8 ppm 6.14 (d, [J=15.] 83 Hz, 1 H) 7.11-7. 16 [(M,] 2 H) 7.68 (d, J=16. 36 Hz, 1 H); MS 233.1 [(M-H) +] ; Purity (HPLC) [94 %.] |
72% | With piperidine In pyridine for 2h; Reflux; | General procedure for the synthesis of the 3-(5-bromo-2-thienyl)acrylic acid 4 and 3-(5-phenyl-2-thienyl)acrylic 5 via Knoevenagel condensation General procedure: 2-Thiophenecarboxyaldehyde derivative (1 eq, 30 mmol) was dissolved in pyridine (60 mL) and piperidine (3 mL). After addition of malonic acid (1.2 eq, 36 mmol), the mixture was refluxed for 2 h. After cooling, the mixture was poured into a mixture of 200 mL water, 200 mL ice and 200 mL concentrated hydrochloric acid to yield a solid. The precipitating solid was filtered off, washed with water and dried under pressure to give the corresponding 3-(2-thienyl)acrylic acid derivative.; 4.1.1.1 3-(5-bromo-2-thienyl)acrylic acid 4 (0023) 1H NMR (DMSO-d6, 250MHz): δ=12.46 (bs, 1H), 7.67 (d, J=15.7Hz, 1H), 7.36 (d, J=3.9Hz, 1H), 7.28 (d, J=3.9Hz, 1H), 6.16 (d, J=15.8Hz, 1H); 13C NMR (DMSO-d6, 62MHz): δ=167.53, 141.25, 136.28, 132.85, 132.28, 118.74, 115.42; LC/MS (ESI): 230.87 [M-H]- and isotopic peak 232.88; HRMS (FAB) cald for C7H4O2SBr (M+H)+ 230.9115, found 230.9131; purity>99%; beige powder. Yield=72%. |
70% | With piperidine; pyridine for 5h; Inert atmosphere; Reflux; | (E)-3-(5-Bromothiophen-2-yl)acrylic acid (SI-2). To a solution of 5-bromothiophene-2-carboxaldehyde (SI-1,32.9 g, 172 mmol) in pyridine (430 mL), malonic acid (54.3 g, 516 mmol) and piperidine (8.6 mL, 86.1 mmol) wasadded. The reaction mixture was heated at reflux for 5 h, cooled to room temperature, and concentrated to give adark oil. The oil was diluted with H2O (500 mL), and a solid precipitate was formed. The suspension was acidifiedto pH 2 with 6 M HCl. The precipitate was filtered and washed with H2O (3 x 50 mL). The filter cake was triturated with EtOAc, and the resulting solid was washed with EtOAc (3 X 50 mL) to give a tan solid (~25 g) that wasdissolved in hot acetone (~700 mL) and filtered through a pad of SiO2. The filtrate was partially concentrated andfiltered. This process was repeated to give an off-white solid (20.5 g). The retained aqueous filtrate wassubsequently reextracted with EtOAc (3 X 100 mL), and the combined organic extracts were washed withsaturated aqueous NaCl, dried (MgSO4), filtered, and added to the EtOAc trituration washings. The dark solutionwas concentrated to give a black residue that was dissolved in hot acetone, filtered through a plug of SiO2, andconcentrated. Trituration of the residue with EtOAc and recrystallization of the resulting solid in acetone gaveadditional off-white solid SI-2 (28.0 g total, 70%): 1H NMR (300 MHz, DMSO-d6): δ 12.46 (brs, 1 H), 7.66 (d, J =15.6 Hz, 1 H), 7.35 (d, J = 3.6 Hz, 1 H), 7.27 (d, J = 4.0 Hz, 1 H), 6.15 (d, J = 16.0 Hz, 1 H). Spectral propertieswere consistent with literature data.1 |
Stage #1: 5-bromo-2-thiophencarboxaldehyde; malonic acid With piperidine; pyridine for 6h; Heating / reflux; Stage #2: With hydrogenchloride In water at 0℃; | 2.a Example 2 3-[5-(4-Chloro-phenyl)-thiophen-2-yl]-1-(piperidin-1-yl)-propenone [Show Image] (a) 3-(5-Bromo-thiophen-2-yl)-acrylic acid 3 g (15.7 mmol) of 5-bromo-thiophene-2-carbaldehyde were dissolved in 30 ml of pyridine and 1.96 g (18.8 mmol) of malonic acid and 133 mg (1.6 mmol) of piperidine was added. The reaction mixture was boiled under reflux for 6 h. After cooling to room temperature, it was poured into a mixture of ice and concentrated aqueous hydrochloric acid whereupon the product precipitated. The product was isolated by filtration, dissolved in ethyl acetate, and the solution was washed with 0.1 M hydrochloric acid. The organic phase was dried with sodium sulfate, filtered and the solvent was removed under reduced pressure. Yield: 3.0 g. MS: m/e = 234 (M+H)+ | |
With piperidine In dimethyl sulfoxide at 100℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83.4% | Stage #1: (E)-3-(5-bromo-2-thienyl)-2-propenoic acid With thionyl chloride In chloroform at 75℃; for 2h; Stage #2: With 1,4-dioxane; sodium azide; water at 0℃; for 0.166667h; | INTERMEDIATE 48 [(2E)-3- (5-BROMOTHIEN-2-YL)] acryloyl azide INTERMEDIATE 48 [(2E)-3- (5-BROMOTHIEN-2-YL)] acryloyl azide Thionyl chloride (1.04 mL) was added to a solution of [(2E)-3- (5-BROMOTHIEN-2-YL)] acrylic acid (1.04 g, 4.46 mmol) in chloroform (20 mL) and the mixture was refluxed for 2h at [75°C] and than used in the next step. The above solution was added drop wise to a stirred suspension of sodium azide (0.58 g, 8.93 mmol), dioxane (3 mL) and water (3 mL) in an ice bath. After 10 min a precipitate appeared which was filtered off and washed with water. The residue was dissolved in dichloromethane, dried with MgS04, filtered and the solvent was removed to afford: 0.96 g (83.4 [%).'H] NMR (270 MHz [CH30H-D4)] 8 ppm 6.20 (d, [J=15.] 57 Hz, 1 H) 7.15-7. 25 (m, 2 H) 7.80 (d, [J=15.] 57 Hz, 1 H); MS 258.1 [(M-H)] [+ ;] Purity (HPLC) 65 %. |
Stage #1: (E)-3-(5-bromo-2-thienyl)-2-propenoic acid With chloroformic acid ethyl ester; triethylamine In acetone at 0℃; for 1.5h; Inert atmosphere; Stage #2: With sodium azide In water; acetone at 0℃; Inert atmosphere; | ||
4.62 g | Stage #1: (E)-3-(5-bromo-2-thienyl)-2-propenoic acid With chloroformic acid ethyl ester; triethylamine In acetone at 0 - 20℃; for 1h; Stage #2: With sodium azide In water; acetone at 0℃; for 1h; | 5.1.22. (E)-3-(5-Bromothiophen-2-yl)acryloyl azide (17a) General procedure: A mixture of ethyl (E)-3-(5-bromothiophen-2-yl)acrylate (16a) (6.34g, 24.3 mmol) and 1 M NaOH aq. (48.6 mL, 48.6 mmol) in THF (20 mL) and MeOH (20 mL) was stirred at rt overnight. The mixture wasneutralized with 1 M HCl aq. and the solution was extracted with EtOAc.The organic layer was separated, washed with brine, dried over Na2SO4and concentrated in vacuo. This residue was used to the next reactionwithout further purification. Ethyl chloroformate (3.49 mL, 36.5 mmol)was added to a mixture of the crude product, TEA (5.09 mL, 36.5 mmol)in acetone (48 mL) at 0 C. After stirring at this temperature for 1 h, amixture of sodium azide (2.52 g, 38.8 mmol) in water (9.5 mL) wasadded dropwise to the reaction mixture. The mixture was stirred at 0 Cfor 1 h. The resulting mixture was poured into water and stirred at rt for10 min. The precipitate was collected by filteration to give the titlecompound as a pale pink solid (4.62 g, 17.9 mmol, 78%). 1H NMR (300MHz, CDCl3) δ 6.10 (1H, d, J = 15.4 Hz), 6.98-7.12 (2H, m), 7.59-7.86(1H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: (E)-3-(5-bromo-2-thienyl)-2-propenoic acid With N-ethylmorpholine;; O-<[cyano(ethoxycarbonyl)methylene]amino>-1,1,3,3-tetramethyluronium tetrafluoroborate In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: piperidine In N,N-dimethyl-formamide at 20℃; for 16h; | 3.a Example 3 3-[5-(4-Fluoro-phenyl)-thiophen-2-yl]-1-(piperidin-1-yl)-propenone [Show Image] (a) 3-(5-Bromo-thiophen-2-yl)-1-(piperidin-1-yl)-propenone; 50 g (2.1 mmol) of 3-(5-bromo-thiophen-2-yl)-acrylic acid, 2.47 g (21.5 mmol) of NEM and 774 mg (2.4 mmol) of TOTU were dissolved in 5 ml of DMF and stirred at room temperature for 15 min. 201 mg (0.5 mmol) of piperidine were added, and the reaction mixture was stirred at room temperature for 16 h. The solvent was removed under reduced pressure. The product was purified by silica gel chromatography. Yield: 458 mg. MS: m/e = 300 (M)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate In 1,2-dimethoxyethane; water at 20 - 95℃; for 20.1667h; | 4.a Example 4 3-[5-(2-Fluoro-phenyl)-th iophen-2-yl]-1-(piperidin-1-yl)-propenone [Show Image] (a) 3-[5-(2-Fluoro-phenyl)-thiophen-2-yl]-acrylic acid; 9.38 g (40.2 mmol) of 3-(5-Bromo-thiophen-2-yl)-acrylic acid and 6.97 g (6 mmol) of tetrakis(triphenylphosphine)palladium were dissolved in 50 ml of degassed DME and stirred for 10 min at room temperature. 8.44 g (60.4 mmol) of 2-fluorophenylboronic acid and 50 ml of a 2 M aqueous sodium carbonate solution were added together with an additional 5 ml of degassed DME. The reaction mixture was heated to 95 °C for 4 h, and then stirred at room temperature for 16 h. The product precipitated partially from the reaction solution and was collected by filtration. This solid was boiled for 1 h in ethyl acetate and filtered while hot. The solvent was removed under reduced pressure. The remaining reaction solution was evaporated to dryness. The residue was taken up in ethyl acetate/water and filtered. The organic phase was dried with sodium sulfate, filtered and the solvent was removed under reduced pressure. The combined product was purified by silica gel chromatography. Yield: 7.5 g. MS: m/e = 249 (M+H)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate In 1,2-dimethoxyethane; water at 25 - 95℃; for 20.1667h; | 2.b (b) 3-[5-(4-Chloro-phenyl)-thiophen-2-yl]-acrylic acid 0.250 g (1.1 mmol) of 3-(5-bromo-thiophen-2-yl)-acrylic acid and 61.9 mg (0.1 mmol) of tetrakis(triphenylphosphine)palladium were dissolved in 5 ml of degassed DME and stirred for 10 min at room temperature. 0.251 g (1.6 mmol) of 4-chlorophenylboronic acid and 1 ml of a 2 M aqueous sodium carbonate solution were added together with an additional 5 ml of degassed DME. The reaction mixture was heated to 95 °C for 4 h, and then stirred at room temperature for 16 h. Solids were removed by filtration and the resulting solution was evaporated to dryness. The residue was dissolved in ethyl acetate and washed three times with a saturated aqueous sodium hydrogencarbonate solution, and once with a saturated sodium chloride solution. The organic phase was dried with sodium sulfate, filtered, and the solvent was removed under reduced pressure. The product was purified by silica gel chromatography. Yield: 0.12 g. MS: m/e = 265 (M+H)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In water; acetonitrile at 160℃; for 0.333333h; Irradiation; | INTERMEDIATE A22 (2JE)-3-(5-{2-[l-(tert-Butoxycarbonyl)piperidin-4-yl]-4H-l,3-benzodioxin-6-yl}-2- thienyl)acrylic acid A suspension of tert-butyi 4-[6-(dimethoxyboryl)-4H-l,3-benzodioxin-2-yl]piperidine-l- carboxylate (Intermediate Al 9; 100 mg, 0.255 mmol), (2E)-3-(5-bromo-2-thienyl)acrylic acid (77.4 mg, 0.332 mmol), K2CO3 (88 mg, 0.64 mmol), PdCfcdppf-DCM (22 mg, 0.025 mmol) in MeCNZH2O (4 mL; 2:1) was heated at 160 0C for 20 min in a microwave reactor. The mixture was filtered through a pad of silica and concentrated to give the title compound which was used directly in Example A137 and A138. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate Reflux; Inert atmosphere; | 1 General procedure for two steps synthesis of 1,3,4-oxadiazole derivatives 8-17 (Method A) and general procedure for one-step synthesis of 1,3,4-oxadiazole derivatives 8-28 (Method B) General procedure: Method A; To a stirred solution of acrylic acid (200mg, 1 eq) and substituted hydrazide (1 eq) in dry ethyl acetate (5-10mL) were added dropwise T3P (2.5 eq, 50% solution in EtOAc) and triethylamine (3 eq), and the mixture was refluxed under argon atmosphere for 1h-24h. The completion of reaction was confirmed by TLC. The mixture was cooled to room temperature, and poured into ice/water. The precipitating solid was filtered off, washed with water, cyclohexan and dried under pressure to give the pure diacylhydrazine derivative. An example of diacylhydrazine derivatives 6-7 synthesis is given below.; 4.1.2.1 N'-[(2E)-3-(5-bromothiophene-2-yl)prop-2-enoyl]-3-chlorobenzohydrazide 6 1H NMR (DMSO-d6, 250 MHz): δ = 10.74 (s, 1H), 10.33 (s, 1H), 8.02 (bs, 1H), 7.95 (d, J = 7.7 Hz, 1H), 7.75 (d, J = 15.6 Hz, 1H), 7.76-7.61 (m, 2H), 7.41 (d, J = 3.9 Hz, 1H), 7.37 (d, J = 3.8 Hz, 1H), 6.52 (d, J = 15.6 Hz, 1H); LC/MS (ESI): 382.84 [M-H]- and isotopic peak: 384.81; purity = 95%. Yield = 59%.; The corresponding diacylhydrazine derivative was placed under argon atmosphere and POCl3 was added dropwise (10 mL). The mixture was refluxed for 1h30. The mixture was cooled to room temperature, and poured into ice/water. The precipitating solid was filtered off, washed with water, cyclohexane and dried under pressure to give the desired 1,3,4-oxadiazole derivative. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate Reflux; Inert atmosphere; | 1 General procedure for two steps synthesis of 1,3,4-oxadiazole derivatives 8-17 (Method A) and general procedure for one-step synthesis of 1,3,4-oxadiazole derivatives 8-28 (Method B) General procedure: Method A; To a stirred solution of acrylic acid (200mg, 1 eq) and substituted hydrazide (1 eq) in dry ethyl acetate (5-10mL) were added dropwise T3P (2.5 eq, 50% solution in EtOAc) and triethylamine (3 eq), and the mixture was refluxed under argon atmosphere for 1h-24h. The completion of reaction was confirmed by TLC. The mixture was cooled to room temperature, and poured into ice/water. The precipitating solid was filtered off, washed with water, cyclohexan and dried under pressure to give the pure diacylhydrazine derivative.; The corresponding diacylhydrazine derivative was placed under argon atmosphere and POCl3 was added dropwise (10 mL). The mixture was refluxed for 1h30. The mixture was cooled to room temperature, and poured into ice/water. The precipitating solid was filtered off, washed with water, cyclohexane and dried under pressure to give the desired 1,3,4-oxadiazole derivative. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate at 160℃; Sealed tube; Inert atmosphere; Microwave irradiation; | 5 General procedure for two steps synthesis of 1,3,4-oxadiazole derivatives 8-17 (Method A) and general procedure for one-step synthesis of 1,3,4-oxadiazole derivatives 8-28 (Method B) General procedure: Method B; To a stirred solution of acrylic acid (200mg, 1 eq) and substituted hydrazide (1 eq) in dry ethyl acetate (5-10mL) were added dropwise T3P (3 eq, 50% solution in EtOAc) and triethylamine (5 eq). The reaction vessel was sealed under argon atmosphere and the mixture was heated under microwave conditions at 160°C for 20min to 30min. The completion of reaction was confirmed by TLC. The mixture was cooled to room temperature. The organic layer was washed twice with 1N HCl, once with H2O and once with brine. The organic layer was dried under Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel flash chromatography (cyclohexan/EtOAc or DCM/Methanol) to afford the desired 1,3,4-oxadiazole derivative.; 4.1.2.5 2-[(E)-2-(5-bromothiophen-2-yl)ethenyl]-5-(3,4-dichlorophenyl)-1,3,4-oxadiazole 10 1H NMR (DMSO-d6, 250 MHz): δ = 8.19 (d, J = 1.9 Hz, 1H), 7.95 (dd, J = 8.5 Hz and J = 2.0 Hz, 1H), 7.84 (d, J = 16.2 Hz, 1H), 7.81 (d, J = 8.4 Hz, 1H), 7.32 (d, J = 3.9 Hz, 1H), 7.22 (d, J = 3.9 Hz, 1H), 6.96 (d, J = 16.2 Hz, 1H); 13C NMR (DMSO-d6, 101 MHz): δ = 164.59, 162.18, 141.88, 135.31, 132.95, 132.46, 132.33, 132.12, 131.75, 128.80, 127.19, 124.39, 115.33, 109.33; LC/MS (ESI): 400.74 [M+H]+ and isotopic peaks: 402.73, 404.74; HRMS (TOF, ESI+) cald for C14H8N2OSCl2Br (M + H)+ 400.8918, found 400.8912; beige powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate at 160℃; Sealed tube; Inert atmosphere; Microwave irradiation; | 7 General procedure for two steps synthesis of 1,3,4-oxadiazole derivatives 8-17 (Method A) and general procedure for one-step synthesis of 1,3,4-oxadiazole derivatives 8-28 (Method B) General procedure: Method B; To a stirred solution of acrylic acid (200mg, 1 eq) and substituted hydrazide (1 eq) in dry ethyl acetate (5-10mL) were added dropwise T3P (3 eq, 50% solution in EtOAc) and triethylamine (5 eq). The reaction vessel was sealed under argon atmosphere and the mixture was heated under microwave conditions at 160°C for 20min to 30min. The completion of reaction was confirmed by TLC. The mixture was cooled to room temperature. The organic layer was washed twice with 1N HCl, once with H2O and once with brine. The organic layer was dried under Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel flash chromatography (cyclohexan/EtOAc or DCM/Methanol) to afford the desired 1,3,4-oxadiazole derivative.; 4.1.2.7 2-[(E)-2-(5-bromothiophen-2-yl)ethenyl]-5-(4-fluorophenyl)-1,3,4-oxadiazole 12 1H NMR (DMSO-d6, 400 MHz): δ = 8.15 (dd, J = 8.8 Hz, 1H), 8.13 (d, J = 8.8 Hz, 1H), 7.87 (d, J = 16.2 Hz, 1H), 7.48 (t, J = 8.8 Hz, 2H), 7.41 (d, J = 3.9 Hz, 1H), 7.31 (d, J = 3.9 Hz, 1H), 7.04 (d, J = 16.2 Hz, 1H); 13C NMR (DMSO-d6, 101 MHz): δ = 164.11, 163.02, 141.82, 132.38, 131.74, 131.52, 129.85, 129.76, 120.48, 120.46, 117.29, 117.07, 115.23, 109.42; LC/MS (ESI): 350.99 [M+H]+ and isotopic peak: 352.98; HRMS (TOF, ESI+) cald for C14H9N2OFSBr (M + H)+ 350.9303, found 350.9599; yellow powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate at 160℃; Sealed tube; Inert atmosphere; Microwave irradiation; | 9 General procedure for two steps synthesis of 1,3,4-oxadiazole derivatives 8-17 (Method A) and general procedure for one-step synthesis of 1,3,4-oxadiazole derivatives 8-28 (Method B) General procedure: Method B; To a stirred solution of acrylic acid (200mg, 1 eq) and substituted hydrazide (1 eq) in dry ethyl acetate (5-10mL) were added dropwise T3P (3 eq, 50% solution in EtOAc) and triethylamine (5 eq). The reaction vessel was sealed under argon atmosphere and the mixture was heated under microwave conditions at 160°C for 20min to 30min. The completion of reaction was confirmed by TLC. The mixture was cooled to room temperature. The organic layer was washed twice with 1N HCl, once with H2O and once with brine. The organic layer was dried under Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel flash chromatography (cyclohexan/EtOAc or DCM/Methanol) to afford the desired 1,3,4-oxadiazole derivative.; 4.1.2.9 2-[(E)-2-(5-bromothiophen-2-yl)ethenyl]-5-(4-methoxyphenyl)-1,3,4-oxadiazole 14 1H NMR (DMSO-d6, 250 MHz): δ = 8.03 (d, J = 8.4 Hz, 2H), 7.84 (d, J = 16.2 Hz, 1H), 7.41 (d, J = 3.5 Hz, 1H), 7.32 (d, J = 3.6 Hz, 1H), 7.18 (d, J = 8.5 Hz, 2H), 7.02 (d, J = 16.2 Hz, 1H), 3.88 (s, 3H); 13C NMR (DMSO-d6, 101 MHz): δ = 163.78, 163.67, 162.68, 141.99, 132.41, 131.66, 131.08, 129.05, 116.13, 115.44, 115.08, 109.67, 56.10; LC/MS (ESI): 362.86 [M+H]+ and isotopic peak: 364.89; HRMS (TOF, ESI+) cald for C15H12N2O2SBr (M + H)+ 362.9803, found 362.9804; beige powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate at 160℃; Sealed tube; Inert atmosphere; Microwave irradiation; | 11 General procedure for two steps synthesis of 1,3,4-oxadiazole derivatives 8-17 (Method A) and general procedure for one-step synthesis of 1,3,4-oxadiazole derivatives 8-28 (Method B) General procedure: Method B; To a stirred solution of acrylic acid (200mg, 1 eq) and substituted hydrazide (1 eq) in dry ethyl acetate (5-10mL) were added dropwise T3P (3 eq, 50% solution in EtOAc) and triethylamine (5 eq). The reaction vessel was sealed under argon atmosphere and the mixture was heated under microwave conditions at 160°C for 20min to 30min. The completion of reaction was confirmed by TLC. The mixture was cooled to room temperature. The organic layer was washed twice with 1N HCl, once with H2O and once with brine. The organic layer was dried under Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel flash chromatography (cyclohexan/EtOAc or DCM/Methanol) to afford the desired 1,3,4-oxadiazole derivative.; 4.1.2.11 2-[(E)-2-(5-bromothiophen-2-yl)ethenyl]-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazole 16 1H NMR (DMSO-d6, 250 MHz): δ = 8.30 (d, J = 8.1 Hz, 2H), 8.02 (d, J = 8.3 Hz, 2H), 7.93 (d, J = 16.2 Hz, 1H), 7.45 (d, J = 4.0 Hz, 1H), 7.33 (d, J = 3.9 Hz, 1H), 7.09 (d, J = 16.2 Hz, 1H); 13C NMR (DMSO-d6, 101 MHz): δ = 164.71, 162.82, 141.81, 132.48, 132.25, 132.12, 132.03, 127.98, 127.62, 126.95, 126.91, 125.65, 122.93, 115.53, 109.34; LC/MS (APCI): 400.86 [M+H]+ and isotopic peak: 402.72; HRMS (TOF, ESI+) cald for C15H9N2OF3SBr (M + H)+ 400.9571, found 400.9574; yellow powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In ethyl acetate; at 160℃;Sealed tube; Inert atmosphere; Microwave irradiation; | General procedure: Method B; To a stirred solution of acrylic acid (200mg, 1 eq) and substituted hydrazide (1 eq) in dry ethyl acetate (5-10mL) were added dropwise T3P (3 eq, 50% solution in EtOAc) and triethylamine (5 eq). The reaction vessel was sealed under argon atmosphere and the mixture was heated under microwave conditions at 160C for 20min to 30min. The completion of reaction was confirmed by TLC. The mixture was cooled to room temperature. The organic layer was washed twice with 1N HCl, once with H2O and once with brine. The organic layer was dried under Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel flash chromatography (cyclohexan/EtOAc or DCM/Methanol) to afford the desired 1,3,4-oxadiazole derivative.; 4.1.2.13 2-(3-bromophenyl)-5-[(E)-2-(5-bromothiophen-2-yl)ethenyl]- 1,3,4-oxadiazole 18 1H NMR (DMSO-d6, 300 MHz): delta = 8.22 (t, J = 1.6 Hz, 1H), 8.08 (dm, J = 8.1 Hz, 1H), 7.91 (d, J = 16.2 Hz, 1H), 7.85 (dm, J = 8.0 Hz, 1H), 7.59 (t, J = 8.0 Hz, 1H), 7.42 (d, J = 3.9 Hz, 1H), 7.31 (d, J = 3.9 Hz, 1H), 7.03 (d, J = 16.2 Hz, 1H); 13C NMR (DMSO-d6, 101 MHz): delta = 164.40, 162.50, 141.82, 135.18, 132.40, 132.10, 131.95, 131.83, 129.43, 126.10, 125.90, 122.93, 115.37, 109.27; LC/MS (ESI): 410.67 [M+H]+ and isotopic peaks: 412.73, 414.78; purity = 95%; HRMS (TOF, ESI+) cald for C14H9N2OSBr2 (M + H)+ 410.8802, found 410.8798; yellow powder. Yield = 49%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate at 160℃; Sealed tube; Inert atmosphere; Microwave irradiation; | 15 General procedure for two steps synthesis of 1,3,4-oxadiazole derivatives 8-17 (Method A) and general procedure for one-step synthesis of 1,3,4-oxadiazole derivatives 8-28 (Method B) General procedure: Method B; To a stirred solution of acrylic acid (200mg, 1 eq) and substituted hydrazide (1 eq) in dry ethyl acetate (5-10mL) were added dropwise T3P (3 eq, 50% solution in EtOAc) and triethylamine (5 eq). The reaction vessel was sealed under argon atmosphere and the mixture was heated under microwave conditions at 160°C for 20min to 30min. The completion of reaction was confirmed by TLC. The mixture was cooled to room temperature. The organic layer was washed twice with 1N HCl, once with H2O and once with brine. The organic layer was dried under Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel flash chromatography (cyclohexan/EtOAc or DCM/Methanol) to afford the desired 1,3,4-oxadiazole derivative.; 4.1.2.15 2-[(E)-2-(5-bromothiophen-2-yl)ethenyl]-5-[(4-N,N-dimethyl)phenyl]-1,3,4-oxadiazole 20 1H RMN (DMSO-d6, 400 MHz): δ = 7.81 (d, J = 8.9 Hz, 2H), 7.72 (d, J = 16.1 Hz, 1H), 7.34 (d, J = 3.8 Hz, 1H), 7.25 (d, J = 3.8 Hz, 1H), 6.94 (d, J = 16.2 Hz, 1H), 6.80 (d, J = 9.0 Hz, 2H), 2.98 (s, 6H); 13C NMR (DMSO-d6, 101 MHz): δ = 164.52, 162.95, 152.89, 142.14, 132.35, 131.40, 130.30, 128.46, 114.75, 112.28, 110.07, 109.86, 40.18; LC/MS (ESI): 375.77 [M+H]+ and isotopic peak: 377.77; purity = 96%; HRMS (TOF, ESI+) cald for C16H15N3OSBr (M + H)+ 376.0119, found 376.0119; orange powder. Yield = 43%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate at 160℃; Sealed tube; Inert atmosphere; Microwave irradiation; | 17 General procedure for two steps synthesis of 1,3,4-oxadiazole derivatives 8-17 (Method A) and general procedure for one-step synthesis of 1,3,4-oxadiazole derivatives 8-28 (Method B) General procedure: Method B; To a stirred solution of acrylic acid (200mg, 1 eq) and substituted hydrazide (1 eq) in dry ethyl acetate (5-10mL) were added dropwise T3P (3 eq, 50% solution in EtOAc) and triethylamine (5 eq). The reaction vessel was sealed under argon atmosphere and the mixture was heated under microwave conditions at 160°C for 20min to 30min. The completion of reaction was confirmed by TLC. The mixture was cooled to room temperature. The organic layer was washed twice with 1N HCl, once with H2O and once with brine. The organic layer was dried under Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel flash chromatography (cyclohexan/EtOAc or DCM/Methanol) to afford the desired 1,3,4-oxadiazole derivative.; 4.1.2.17 2-[(E)-2-(5-bromothiophen-2-yl)ethenyl]-5-phenyl-1,3,4-oxadiazole 22 1H RMN (DMSO-d6, 400 MHz): δ = 8.04 (dd, J = 7.6 Hz and J = 1.9 Hz, 2H), 7.83 (d, J = 16.2 Hz, 1H), 7.62-7.56 (m, 3H), 7.38 (d, J = 3.9 Hz, 1H), 7.27 (d, J = 3.9 Hz, 1H), 7.01 (d, J = 16.1 Hz, 1H); 13C NMR (DMSO-d6, 101 MHz): δ = 164.15, 163.81, 141.91, 132.60, 132.43, 131.85, 131.55, 129.96, 127.16, 123.80, 115.29, 109.53; LC/MS (ESI): 332.80 [M+H]+ and isotopic peak: 334.76; purity = 96%; HRMS (TOF, ESI+) cald for C14H10N2OSBr (M + H)+ 332.9697, found 332.9696; yellow powder. Yield = 15%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate at 160℃; Sealed tube; Inert atmosphere; Microwave irradiation; | 19 General procedure for two steps synthesis of 1,3,4-oxadiazole derivatives 8-17 (Method A) and general procedure for one-step synthesis of 1,3,4-oxadiazole derivatives 8-28 (Method B) General procedure: Method B; To a stirred solution of acrylic acid (200mg, 1 eq) and substituted hydrazide (1 eq) in dry ethyl acetate (5-10mL) were added dropwise T3P (3 eq, 50% solution in EtOAc) and triethylamine (5 eq). The reaction vessel was sealed under argon atmosphere and the mixture was heated under microwave conditions at 160°C for 20min to 30min. The completion of reaction was confirmed by TLC. The mixture was cooled to room temperature. The organic layer was washed twice with 1N HCl, once with H2O and once with brine. The organic layer was dried under Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel flash chromatography (cyclohexan/EtOAc or DCM/Methanol) to afford the desired 1,3,4-oxadiazole derivative.; 4.1.2.19 2-[(E)-2-(5-bromothiophen-2-yl)ethenyl]-5-(4-chlorophenyl)-1,3,4-oxadiazole 24 1H NMR (DMSO-d6, 250 MHz): δ = 8.04 (d, J = 8.6 Hz, 2H), 7.83 (d, J = 16.2 Hz, 1H), 7.66 (d, J = 8.6 Hz, 2H), 7.37 (d, J = 3.9 Hz, 1H), 7.27 (d, J = 3.8 Hz, 1H), 7.00 (d, J = 16.2 Hz, 1H); 13C NMR (DMSO-d6, 101 MHz): δ = 164.31, 163.09, 141.87, 137.32, 132.45, 131.86, 131.76, 130.14, 128.94, 122.72, 115.35, 109.43; LC/MS (ESI): 366.74 [M+H]+ and isotopic peak: 368.72; purity = 95%; HRMS (TOF, ESI+) cald for C14H9N2OSClBr (M + H)+ 366.9307, found 366.9306; yellow powder. Yield = 38%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate at 160℃; Sealed tube; Inert atmosphere; Microwave irradiation; | 20 General procedure for two steps synthesis of 1,3,4-oxadiazole derivatives 8-17 (Method A) and general procedure for one-step synthesis of 1,3,4-oxadiazole derivatives 8-28 (Method B) General procedure: Method B; To a stirred solution of acrylic acid (200mg, 1 eq) and substituted hydrazide (1 eq) in dry ethyl acetate (5-10mL) were added dropwise T3P (3 eq, 50% solution in EtOAc) and triethylamine (5 eq). The reaction vessel was sealed under argon atmosphere and the mixture was heated under microwave conditions at 160°C for 20min to 30min. The completion of reaction was confirmed by TLC. The mixture was cooled to room temperature. The organic layer was washed twice with 1N HCl, once with H2O and once with brine. The organic layer was dried under Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel flash chromatography (cyclohexan/EtOAc or DCM/Methanol) to afford the desired 1,3,4-oxadiazole derivative.; 4.1.2.20 2-(4-bromophenyl)-5-[(E)-2-(5-bromothiophen-2-yl)ethenyl]-1,3,4-oxadiazole 25 1H RMN (DMSO-d6, 400 MHz): δ = 8.02 (d, J = 8.6 Hz, 2H), 7.91 (d, J = 16.2 Hz, 1H), 7.86 (d, J = 8.7 Hz, 2H), 7.43 (d, J = 3.9 Hz, 1H), 7.33 (d, J = 3.9 Hz, 1H), 7.06 (d, J = 16.2 Hz, 1H); 13C NMR (DMSO-d6, 101 MHz): δ = 164.26, 163.13, 141.81, 133.00, 132.39, 131.84, 131.72, 128.99, 126.16, 122.98, 115.33, 109.35; LC/MS (ESI): 410.68 [M+H]+ and isotopic peaks: 412.69, 414.69; purity = 97%; HRMS (TOF, ESI+) cald for C14H9N2OSBr2 (M + H)+ 410.8802, found 410.8805; yellow powder. Yield = 27%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate at 160℃; Sealed tube; Inert atmosphere; Microwave irradiation; | 21 General procedure for two steps synthesis of 1,3,4-oxadiazole derivatives 8-17 (Method A) and general procedure for one-step synthesis of 1,3,4-oxadiazole derivatives 8-28 (Method B) General procedure: Method B; To a stirred solution of acrylic acid (200mg, 1 eq) and substituted hydrazide (1 eq) in dry ethyl acetate (5-10mL) were added dropwise T3P (3 eq, 50% solution in EtOAc) and triethylamine (5 eq). The reaction vessel was sealed under argon atmosphere and the mixture was heated under microwave conditions at 160°C for 20min to 30min. The completion of reaction was confirmed by TLC. The mixture was cooled to room temperature. The organic layer was washed twice with 1N HCl, once with H2O and once with brine. The organic layer was dried under Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel flash chromatography (cyclohexan/EtOAc or DCM/Methanol) to afford the desired 1,3,4-oxadiazole derivative.; 4.1.2.21 2-[(E)-2-(5-bromothiophen-2-yl)ethenyl]-5-(3-fluorophenyl)-1,3,4-oxadiazole 26 1H RMN (DMSO-d6, 250 MHz): δ = 7.99 (d, J = 16.1 Hz, 1H), 7.99-7.91 (m, 2H), 7.75 (dd, J = 7.9 Hz and J = 2.1 Hz, 1H), 7.58 (td, J = 8.7 Hz and J = 1.9 Hz, 1H), 7.49 (d, J = 3.9 Hz, 1H), 7.39 (d, J = 3.8 Hz, 1H), 7.13 (d, J = 16.2 Hz, 1H); 13C NMR (DMSO-d6, 101 MHz): δ = 164.41, 162.83, 141.85, 132.46, 132.39 (C-F), 132.31, 131.96, 131.87, 125.80, 123.41, 119.62, 119.41, 115.43, 114.08, 113.84, 109.34; LC/MS (ESI): 350.78 [M+H]+ and isotopic peak: 352.87; purity = 97%; HRMS (TOF, ESI+) cald for C14H9N2OSBrF (M + H)+ 350.9603, found 350.9605; yellow powder. Yield = 33%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate at 160℃; Sealed tube; Inert atmosphere; Microwave irradiation; | 22 General procedure for two steps synthesis of 1,3,4-oxadiazole derivatives 8-17 (Method A) and general procedure for one-step synthesis of 1,3,4-oxadiazole derivatives 8-28 (Method B) General procedure: Method B; To a stirred solution of acrylic acid (200mg, 1 eq) and substituted hydrazide (1 eq) in dry ethyl acetate (5-10mL) were added dropwise T3P (3 eq, 50% solution in EtOAc) and triethylamine (5 eq). The reaction vessel was sealed under argon atmosphere and the mixture was heated under microwave conditions at 160°C for 20min to 30min. The completion of reaction was confirmed by TLC. The mixture was cooled to room temperature. The organic layer was washed twice with 1N HCl, once with H2O and once with brine. The organic layer was dried under Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel flash chromatography (cyclohexan/EtOAc or DCM/Methanol) to afford the desired 1,3,4-oxadiazole derivative.; 4.1.2.22 2-[(E)-2-(5-bromothiophen-2-yl)ethenyl]-5-(3,5-dichlorophenyl)-1,3,4-oxadiazole 27 1H RMN (DMSO-d6, 400 MHz): δ = 8.02 (d, J = 1.9 Hz, 2H), 7.90 (d, J = 16.1 Hz, 1H), 7.87 (t, J = 1.9 Hz, 1H), 7.36 (d, J = 3.9 Hz, 1H), 7.26 (d, J = 3.9 Hz, 1H), 6.99 (d, J = 16.1 Hz, 1H); 13C NMR (DMSO-d6, 101 MHz): δ = 164.72, 161.69, 141.81, 135.75, 132.48, 132.43, 131.94, 131.81, 126.98, 125.56, 115.62, 109.10; LC/MS (ESI): 400.71 [M+H] + and isotopic peaks: 402.70, 404.68; purity = 98%; HRMS (TOF, ESI+) cald for C14H8N2OSCl2Br (M + H)+ 400.8918, found 400.8921; yellow powder. Yield = 55%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate at 160℃; Sealed tube; Inert atmosphere; Microwave irradiation; | 23 General procedure for two steps synthesis of 1,3,4-oxadiazole derivatives 8-17 (Method A) and general procedure for one-step synthesis of 1,3,4-oxadiazole derivatives 8-28 (Method B) General procedure: Method B; To a stirred solution of acrylic acid (200mg, 1 eq) and substituted hydrazide (1 eq) in dry ethyl acetate (5-10mL) were added dropwise T3P (3 eq, 50% solution in EtOAc) and triethylamine (5 eq). The reaction vessel was sealed under argon atmosphere and the mixture was heated under microwave conditions at 160°C for 20min to 30min. The completion of reaction was confirmed by TLC. The mixture was cooled to room temperature. The organic layer was washed twice with 1N HCl, once with H2O and once with brine. The organic layer was dried under Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel flash chromatography (cyclohexan/EtOAc or DCM/Methanol) to afford the desired 1,3,4-oxadiazole derivative.; 4.1.2.23 2-[(E)-2-(5-bromothiophen-2-yl)ethenyl]-5-(3-methoxyphenyl)-1,3,4-oxadiazole 28 1H RMN (DMSO-d6, 250 MHz): δ = 7.96 (d, J = 16.2 Hz, 1H), 7.73 (d, J = 8.0 Hz, 1H), 7.64 (d, J = 1.8 Hz, 1H), 7.59 (d, J = 7.9 Hz, 1H), 7.49 (d, J = 4.0 Hz, 1H), 7.38 (d, J = 3.9 Hz, 1H), 7.28 (dd, J = 8.2 Hz and J = 2.6 Hz, 1H), 7.12 (d, J = 16.2 Hz, 1H), 3.93 (s, 3H); 13C NMR (DMSO-d6, 101 MHz): δ = 164.21, 163.72, 160.25, 141.94, 132.46, 131.86, 131.65, 131.29, 124.98, 119.48, 118.52, 115.34, 112.08, 109.51, 56.04; LC/MS (ESI): 362.80 [M+H]+ and isotopic peak: 364.80; purity = 98%; HRMS (TOF, ESI+) cald for C15H12N2O2SBr (M + H)+ 362.9803, found 362.9807; brown solid. Yield = 18%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate Reflux; Inert atmosphere; | 1 General procedure for two steps synthesis (Method C) and one-step synthesis (Method D) of 1,2,4-oxadiazole derivatives 33-36 General procedure: Method C; To a stirred solution of acrylic acid (200mg, 1 eq) and substituted amidoxime (1 eq) in dry ethyl acetate (5-10mL) were added dropwise T3P (2.5 eq, 50% solution in EtOAc) and triethylamine (3 eq-5 eq), and the mixture was refluxed under argon atmosphere for 24h. The completion of reaction was confirmed by TLC. The mixture was cooled to room temperature and poured into ice/water. The aqueous layer was extracted twice with EtOAc and then the organic layer was washed twice with saturated NaHCO3, and once with brine. The organic layer was dried under Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel flash chromatography (cyclohexan/EtOAc) to afford the desired acylamidoxime. An example of the acylamidoxime derivative 29 synthesis is given below.; 4.1.3.1 (E)-[amino(4-chlorophenyl)methylidene]amino-(2E)-3-(5-bromothiophen-2-yl)prop-2-enoate 29 1H NMR (acetone-d6, 250 MHz): δ = 7.72 (d, J = 8.8 Hz, 2H), 7.70 (d, J = 15.7 Hz, 1H), 7.36 (d, J = 8.8 Hz, 2H), 7.18 (d, J = 3.9 Hz, 1H), 7.09 (d, J = 3.9 Hz, 1H), 6.38 (bs, 2H), 6.33 (d, J = 15.8 Hz, 1H); LC/MS (ESI): 382.74 [M-H]- and isotopic peak: 384.81, 384.80 [M+H]+ and isotopic peak: 386.85; purity = 98%; beige powder. Yield = 9%. The corresponding acylamidoxime (1 eq) was placed under argon atmosphere, anhydrous THF (3 mL) and TBAF (0.1 eq, 1 M in THF) was added. The mixture was stirred at room temperature for 16-18 h. The completion of reaction was confirmed by TLC. The solvent was evaporated and EtOAc was added. The organic layer was washed twice with water and twice with brine. The organic layer was dried under Na2SO4 and concentrated under reduced pressure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate at 160℃; for 0.5h; Sealed tube; Inert atmosphere; Microwave irradiation; | 3 General procedure for two steps synthesis (Method C) and one-step synthesis (Method D) of 1,2,4-oxadiazole derivatives 33-36 General procedure: Method D; To a stirred solution of acrylic acid (200mg, 1 eq) and substituted (1 eq) in dry ethyl acetate (5-10mL) were added dropwise T3P (3 eq, 50% solution in EtOAc) and triethylamine (5 eq). The reaction vessel was sealed under argon atmosphere and the mixture was heated under microwave conditions at 160°C for 30min. The completion of reaction was confirmed by TLC. The mixture was cooled to room temperature. The organic layer was washed twice with 1N HCl, once with H2O and once with brine. The organic layer was dried under Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel flash chromatography (cyclohexan/EtOAc) to afford the desired 1,2,4-oxadiazole derivative.; 4.1.3.3 5-[(E)-2-(5-bromothiophen-2-yl)ethenyl]-3-(3-chlorophenyl)-1,2,4-oxadiazole 34 1H NMR (DMSO-d6, 400 MHz): δ = 8.07 (d, J = 16.0 Hz, 1H), 8.02-7.97 (m, 2H), 7.66-7.59 (m, 1H), 7.63 (t, J = 7.8 Hz, 1H), 7.52 (d, J = 4.0 Hz, 1H), 7.35 (d, J = 3.9 Hz, 1H), 7.09 (d, J = 16.1 Hz, 1H); 13C NMR (DMSO-d6, 101 MHz): δ = 175.79, 167.43, 141.30, 135.46, 134.40, 133.56, 132.54, 131.93, 131.83, 128.70, 127.05, 126.10, 116.80, 109.27; LC/MS (APCI): 366.59 [M-H-] and isotopic peak 368.56, 368.70 [M + H+] and isotopic peak: 370.10; HRMS (TOF, ESI+) cald for C14H9N2OSClBr (M + H)+ 366.9307, found 366.9310; pale orange powder. Method C - Two-step conversion yield determined by LC/MS = 8%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate Reflux; Inert atmosphere; | 1 General procedure for two steps synthesis (Method C) and one-step synthesis (Method D) of 1,2,4-oxadiazole derivatives 33-36 General procedure: Method C; To a stirred solution of acrylic acid (200mg, 1 eq) and substituted amidoxime (1 eq) in dry ethyl acetate (5-10mL) were added dropwise T3P (2.5 eq, 50% solution in EtOAc) and triethylamine (3 eq-5 eq), and the mixture was refluxed under argon atmosphere for 24h. The completion of reaction was confirmed by TLC. The mixture was cooled to room temperature and poured into ice/water. The aqueous layer was extracted twice with EtOAc and then the organic layer was washed twice with saturated NaHCO3, and once with brine. The organic layer was dried under Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel flash chromatography (cyclohexan/EtOAc) to afford the desired acylamidoxime.; The corresponding acylamidoxime (1 eq) was placed under argon atmosphere, anhydrous THF (3 mL) and TBAF (0.1 eq, 1 M in THF) was added. The mixture was stirred at room temperature for 16-18 h. The completion of reaction was confirmed by TLC. The solvent was evaporated and EtOAc was added. The organic layer was washed twice with water and twice with brine. The organic layer was dried under Na2SO4 and concentrated under reduced pressure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate at 160℃; for 0.5h; Sealed tube; Inert atmosphere; Microwave irradiation; | 4 General procedure for two steps synthesis (Method C) and one-step synthesis (Method D) of 1,2,4-oxadiazole derivatives 33-36 General procedure: Method D; To a stirred solution of acrylic acid (200mg, 1 eq) and substituted (1 eq) in dry ethyl acetate (5-10mL) were added dropwise T3P (3 eq, 50% solution in EtOAc) and triethylamine (5 eq). The reaction vessel was sealed under argon atmosphere and the mixture was heated under microwave conditions at 160°C for 30min. The completion of reaction was confirmed by TLC. The mixture was cooled to room temperature. The organic layer was washed twice with 1N HCl, once with H2O and once with brine. The organic layer was dried under Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel flash chromatography (cyclohexan/EtOAc) to afford the desired 1,2,4-oxadiazole derivative.; 4.1.3.4 5-[(E)-2-(5-bromothiophen-2-yl)ethenyl]-3-[4-trifluoro(methoxy)phenyl]-1,2,4-oxadiazole 35 1H NMR (DMSO-d6, 400 MHz): δ = 8.07 (d, J = 8.9 Hz, 2H), 7.97 (d, J = 16.1 Hz, 1H), 7.50 (d, J = 8.8 Hz, 2H), 7.44 (d, J = 4.0 Hz, 1H), 7.26 (d, J = 3.9 Hz, 1H), 7.01 (d, J = 16.1 Hz, 1H); 13C NMR (DMSO-d6, 101 MHz): δ = 175.73, 167.50, 150.91, 150.89, 141.31, 135.35, 133.53, 132.53, 129.73, 125.87, 122.11, 116.76, 109.35; LC/MS (ESI): 415.26 [M-H]- and isotopic peak: 417.22; HRMS (TOF, ESI+) cald for C15H9N2O2F3SBr (M + H)+ 416.9520, found 416.9520; yellow powder. Method C - Two-step conversion yield determined by LC/MS = 5%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate Reflux; Inert atmosphere; | 1 General procedure for two steps synthesis (Method C) and one-step synthesis (Method D) of 1,2,4-oxadiazole derivatives 33-36 General procedure: Method C; To a stirred solution of acrylic acid (200mg, 1 eq) and substituted amidoxime (1 eq) in dry ethyl acetate (5-10mL) were added dropwise T3P (2.5 eq, 50% solution in EtOAc) and triethylamine (3 eq-5 eq), and the mixture was refluxed under argon atmosphere for 24h. The completion of reaction was confirmed by TLC. The mixture was cooled to room temperature and poured into ice/water. The aqueous layer was extracted twice with EtOAc and then the organic layer was washed twice with saturated NaHCO3, and once with brine. The organic layer was dried under Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel flash chromatography (cyclohexan/EtOAc) to afford the desired acylamidoxime.; The corresponding acylamidoxime (1 eq) was placed under argon atmosphere, anhydrous THF (3 mL) and TBAF (0.1 eq, 1 M in THF) was added. The mixture was stirred at room temperature for 16-18 h. The completion of reaction was confirmed by TLC. The solvent was evaporated and EtOAc was added. The organic layer was washed twice with water and twice with brine. The organic layer was dried under Na2SO4 and concentrated under reduced pressure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate at 160℃; for 0.5h; Sealed tube; Inert atmosphere; Microwave irradiation; | 5 General procedure for two steps synthesis (Method C) and one-step synthesis (Method D) of 1,2,4-oxadiazole derivatives 33-36 General procedure: Method D; To a stirred solution of acrylic acid (200mg, 1 eq) and substituted (1 eq) in dry ethyl acetate (5-10mL) were added dropwise T3P (3 eq, 50% solution in EtOAc) and triethylamine (5 eq). The reaction vessel was sealed under argon atmosphere and the mixture was heated under microwave conditions at 160°C for 30min. The completion of reaction was confirmed by TLC. The mixture was cooled to room temperature. The organic layer was washed twice with 1N HCl, once with H2O and once with brine. The organic layer was dried under Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel flash chromatography (cyclohexan/EtOAc) to afford the desired 1,2,4-oxadiazole derivative.; 4.1.3.5 5-[(E)-2-(5-bromothiophen-2-yl)ethenyl]-3-[(4-trifluoromethyl)phenyl]-1,2,4-oxadiazole 36 1H NMR (DMSO-d6, 400 MHz): δ = 8.24 (d, J = 8.1 Hz, 2H), 8.08 (d, J = 16.1 Hz, 1H), 7.96 (d, J = 8.3 Hz, 2H), 7.53 (d, J = 4.0 Hz, 1H), 7.35 (d, J = 3.9 Hz, 1H), 7.11 (d, J = 16.1 Hz, 1H); 13C NMR (DMSO-d6, 101 MHz): δ = 175.95, 167.52, 141.28, 135.51, 133.62, 132.54, 132.01, 128.33, 126.78, 126.75, 126.71, 126.67, 125.66, 122.96, 116.85, 109.25; LC/MS (ESI): 401.14 [M-H]-; HRMS (TOF, ESI+) cald for C15H9N2OF3SBr (M + H)+ 400.9571, found 400.9570; yellow powder. Method C - Two-step conversion yield determined by LC/MS = 3%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate at 160℃; for 0.5h; Sealed tube; Inert atmosphere; Microwave irradiation; | 2 General procedure for two steps synthesis (Method C) and one-step synthesis (Method D) of 1,2,4-oxadiazole derivatives 33-36 General procedure: Method D; To a stirred solution of acrylic acid (200mg, 1 eq) and substituted (1 eq) in dry ethyl acetate (5-10mL) were added dropwise T3P (3 eq, 50% solution in EtOAc) and triethylamine (5 eq). The reaction vessel was sealed under argon atmosphere and the mixture was heated under microwave conditions at 160°C for 30min. The completion of reaction was confirmed by TLC. The mixture was cooled to room temperature. The organic layer was washed twice with 1N HCl, once with H2O and once with brine. The organic layer was dried under Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel flash chromatography (cyclohexan/EtOAc) to afford the desired 1,2,4-oxadiazole derivative.; 4.1.3.2 5-[(E)-2-(5-bromothiophen-2-yl)ethenyl]-3-(4-chlorophenyl)-1,2,4-oxadiazole 33 1H NMR (DMSO-d6, 400 MHz): δ = 8.02 (d, J = 8.5 Hz, 2H), 7.99 (d, J = 16.3 Hz, 1H), 7.62 (d, J = 8.5 Hz, 2H), 7.48 (d, J = 4.0 Hz, 1H), 7.30 (d, J = 3.9 Hz, 1H), 7.05 (d, J = 16.2 Hz, 1H); 13C NMR (DMSO-d6, 101 MHz): δ = 175.74, 167.75, 141.37, 136.84, 135.39, 133.61, 132.60, 129.99, 129.33, 125.62, 116.82, 109.42; LC/MS (ESI): 364.80 [M-H]- and isotopic peak: 366.77, 366.73 [M+H]+ and isotopic peak: 368.77; HRMS (TOF, ESI+) cald for C14H9N2OSClBr (M + H)+ 366.9307, found 366.9307; yellow powder. Method C - Two-step conversion yield determined by LC/MS = 8%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; dichloromethane at 20℃; for 5h; | 1 Procedure A General procedure: To a stirred solution of 3-(Thien-2-yl)- or 3-(Thiazol-5-yl)acrylic acid derivative (1.5eq, 200mg) and substituted aniline (l eq) in dry dichloromethane or in dry THF (20mL), l -(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2eq) and DMAP (2eq) were added. The reaction mixture was stirred at room temperature for 5h. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was poured into IN aqueous solution of hydrochloric acid (lOmL). At this stage, compounds 9, 33, 53 and 99 precipitated. Precipitates were filtered off, washed with water and dried to afford pure hydrochloride salts. For all other compounds, the organic layer was washed twice with IN aqueous solution of hydrochloric acid (IN), then twice with saturated NaHCC , water and brine. The organic layer was dried under MgS04, then filtered off and concentrated under reduced pressure. The crude product was purified by flash chromatography (cyclohexane/ethyl acetate or dichloromethane/methanol) afforded the final product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | Stage #1: chloroformic acid ethyl ester; (E)-3-(5-bromo-2-thienyl)-2-propenoic acid With triethylamine In acetone at 0℃; for 1.5h; Stage #2: With sodium azide In water; acetone at 0℃; for 0.25h; Stage #3: With tributyl-amine In diphenylether; dichloromethane at 240℃; for 0.916667h; | [0099] 2-Bromothieno[3,2-c]pyridin-4(5Lf)-one (6). Et3N (6.02 mL, 42.9 mmol) was added to a solution of (A)-3 -(5 -bromothiophen-2-yl (acrylic acid (5, 5.00 g, 21.4 mmol) in acetone (55 mL) at 0 °C (ice-bath). Ethyl chloroformate (6.25 mL, 64.3 mmol) was then added, and the reaction mixture was stirred at 0 °C for 1.5 h. A solution of NaN3 (2.09 g, 32.1 mmol) in H2O (16 mL) was added to this reaction mixture slowly at 0 °C (ice-bath). The mixture became homogeneous, and then a solid began to precipitate. Stirring was continued for 15 min. The reaction mixture was poured into ice-chilled H2O (30 mL) and extracted with EtOAc (3 x 30 mL). The combined organic layers were dried (MgSCL), filtered and concentrated to give crude acyl azide as a tan solid that was used for the next step without further purification. (0147) [00100] A 3-neck flask fitted with a stopper, addition funnel, and condenser was charged with BU3N (6.63 mL, 27.8 mmol) and PI12C) (20 mL). The solution was heated to 240 °C. The addition funnel was charged with a solution of the crude acyl azide (5.53 g, 21.4 mmol) in CH2CI2 (50 mL). The acyl azide solution was added to the hot reaction mixture over a period of ca. 40 min, allowing the CH2CI2 to boil off. The mixture was stirred at 240 °C for another 15 min, cooled to rt, and hexanes (20 mL) was added, at which point a solid began to precipitate. The hexane layer was decanted, and the remaining residue was suspended in EtOAc (15 mL). A tan solid precipitated out of solution and was filtered to give 6 (2.56 g, 52%) : Mp >250 °C; IR (ATR) Vmax 2809, 1637, 1607, 1513, 1472, 1274, 1222, 1144, 994, 928, 803, 762, 692 cm 1; NMR (400 MHz, DMSO-de) d 11.54 (brs, 1 H), 7.54 (d, J= 0.4 Hz, 1 H), 7.28-7.25 (m, 1 H), 6.81 (d, J= 6.8 Hz, 1 H); 13C NMR (100 MHz, DMSO-de) d 157.5, 149.7, 130.7, 130.4, 126.8, 111.4, 100.5; HRMS (ESI+) m/z calcd for C7H5ONSBr (M+H) 229.9270, found 229.9270. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: chloroformic acid ethyl ester; (E)-3-(5-bromo-2-thienyl)-2-propenoic acid With triethylamine In water; acetone at 0℃; for 0.5h; Inert atmosphere; Stage #2: With sodium azide In water; acetone at 0℃; Inert atmosphere; | 2-Bromothieno[3,2-c]pyridin-4(5H)-one (SI-3). Triethylamine (6.63 mL, 47.2 mmol) was added to a solution of(E)-3-(5-bromothiophen-2-yl)acrylic acid (SI-2, 5.50 g, 23.6 mmol) in acetone (55 mL) at 0 °C (ice-bath). Subsequently, ethyl chloroformate (6.76 mL, 70.8 mmol) was added, and the reaction mixture was stirred at 0 °C for 30 min. A solution of NaN3 (2.30 g, 35.4 mmol) in H2O (17 mL) was slowly added to the reaction mixture at 0°C. The mixture became homogeneous before a solid began to precipitate. The mixture was stirred for 15 min.The reaction mixture was poured into ice-chilled H2O (30 mL), extracted with EtOAc (3 x 40 mL), and thecombined organic layers were dried (MgSO4), filtered, and concentrated to give crude acyl azide as a tan solidthat was used for the next step without further purification. |
Tags: 50868-68-3 synthesis path| 50868-68-3 SDS| 50868-68-3 COA| 50868-68-3 purity| 50868-68-3 application| 50868-68-3 NMR| 50868-68-3 COA| 50868-68-3 structure
[ 29079-97-8 ]
3-(5-Bromothiophen-2-yl)acrylic acid
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3-(5-Bromothiophen-2-yl)acrylic acid
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