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CAS No. : | 19075-59-3 | MDL No. : | MFCD12032270 |
Formula : | C9H5BrO2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YYKIKWNYRWUIKB-UHFFFAOYSA-N |
M.W : | 257.10 | Pubchem ID : | 17979583 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With acetic acid; silver carbonate In dimethyl sulfoxide at 120℃; for 16 h; | A mixture 3a or 4b (0.5 mmol), Ag2CO3 (0.05 mmol), AcOH(0.025 mmol) in DMSO (1.0 mL)was stirred at 120 °C. After 16 h, thereactionwas cooled down to room temperature and quenched with1 M hydrochloric acid solution (2 mL) and the aqueous phaseextracted with ethyl acetate. The combined organic layers werewashed with brine and dried sodium sulfate, filtered, and the solventswere removed under reduced pressure to give analyticallypure 4a or 4b. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With sodium hydroxide In methanol for 2 h; Reflux | The second step in the preparation of methyl 7-bromo-benzo [b] thiophene-2- carboxylate 64 mg (0.22 mmol) was dissolved in a 3 ml of methanol and then, 3N sodium hydroxide, 240 ul (0.72 mmol) was added 2 hours and heated to reflux. The reaction mixture was acidified with 3N hydrochloric acid and extracted with ethyl acetate 30 ml. It was charged and the organic dried and concentrated under reduced pressure over anhydrous sodium sulfate (Na2SO4). To give the 62 mg yield as a white solid target compound without a residue purified by silica gel column chromatography 100percent (0.24 mmol). |
96% | Stage #1: With potassium hydroxide In water for 3 h; Reflux Stage #2: With hydrogenchloride In water |
General procedure: The solution of compound 2a or 2b (1.1 mmol) in water (10 mL)was stirred and then potassium hydroxide pellets (5.4 mmol) wasadded, which was refluxed for 3 h. The aqueous layer was thenacidified to pH 1 with 1 M hydrochloric acid solution. The aqueouslayer was extracted with dichloromethane (3 15 mL). The combinedorganic layers were dried with sodium sulfate, filtered, andthe solvents were removed under reduced pressure to afford thetitle compound 3a or 3b. |
272 mg | With lithium hydroxide monohydrate In methanol; water at 75℃; for 2 h; | A mixture of 300 mg of methyl 7-bromobenzo[b]thiophene-2-carboxylate, 100 mg of lithium hydroxide monohydrate,3 ml of water, and 9 ml of methanol was stirred for 2 hours at 75°C. The reaction mixture was concentratedunder reduced pressure. Water was added to the residues, and the residue was washed three times with tert-butylmethyl ether. Concentrated hydrochloric acid was added to the aqueous layer, and then extraction was performed threetimes by using tert-butyl methyl ether. The collected organic layer was washed with saturated saline, dried over magnesiumsulfate, and then concentrated under reduced pressure, thereby obtaining 272 mg of 7-bromobenzo[b]thiophene-2-carboxylic acid (hereinafter, described as a "compound 13 of the present invention"). 1H-NMR (DMSO-D6) δ: 13.74 (br s, 1H), 8.27 (s, 1H), 8.06 (dd, 1H, J = 7.8, 0.9 Hz), 7.78 (dd, 1H, J = 7.8, 0.9 Hz), 7.44(t, 1H, J = 7.8 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | Zu einer [AUF 0C] gekuehlten Loesung von 4.0 g (15.6 mmol) [7-BROM-L-BENZOTHIOPHEN-] 2-carbonsaeure (Beispiel 7A) und 3.10 [G] (15.6 mmol) (S)-3-Aminochinuklidin- Dihydrochlorid in 50 mL DMF werden 3.58 g (18.7 mmol) EDC, 2.52 g (18.7 mmol) HOBt und 7.8 mL (56 mmol) Triethylamin zugegeben. Bei Raumtemperatur wird [18] geruehrt. Die Reaktion wird durch Zugabe von 10%-iger [NATRIUMHYDROGEN-] carbonat-Loesung abgebrochen. Der nach der Zugabe von Essigsaeureethylester [ENT-] stehende Niederschlag wird abfiltriert. Die waessrige Phase wird mit Essigsaeure- ethylester extrahiert, die vereinigten organischen Phasen werden ueber Natriumsulfat getrocknet, eingeengt und der Rueckstand im Hochvakuum getrocknet. Man erhaelt 4.70 g (68 % d. Th. ) der Titelverbindung. Die spektroskopischen Daten stimmen mit denen der enantiomeren Verbindung (Beispiel 8A) ueberein. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2-(7-aza-1H-benzotriazol-1-yl)-1,1,3,3-tetratetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); | 903.8 mg (3.52 mmol) [7-BROM-L-BENZOTHIOPHEN-2-CARBONSaeURE] (Beispiel 7A), 700 mg (3.52 mmol) (R)-3-Aminochinuklidin-Dihydrochlorid, 1604.0 mg (4.22 mmol) HATU, [1635.] 7 mg (12.66 mmol) N, N-Diisopropylethylamin und 7.0 [ML] DMF werden gemaess der allgemeinen Arbeitsvorschrift C umgesetzt. Das Reaktionsgemisch wird durch praeparative HPLC gereinigt. Das Produkt wird in einem [1] : l-Gemisch aus 4 M Chlorwasserstoff in Dioxan und 1 N Salzsaeure geloest, anschliessend eingeengt und im Hochvakuum getrocknet. Es werden 1087 mg (77 % d. Th. ) der Titelverbindung erhalten. [H-NMR] (200 MHz, DMSO-d6) : [8] = 10.01 (br. [S,] 1H), 9.15 (d, 1H), 8.47 (s, 1H), 8.02 (m, 1H), 7.74 (m, 1H), 7.43 (dd, 1H), 4.34 (m, [1H),] 3.80-3. 10 (m, [6H),] 2.22 [(M,] 1H), 2.14 (m, 1H), 1.93 (m, 2H), 1.78 (m, 1H). HPLC (Methode [1)] : Rt = 4.1 min. MS (ESIpos) : m/z = 365 (M+H) [+] (freie Base). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydride; | Ausgehend von 27.8 g (137.1 mmol) 3-Brom-2-fluorbenzaldehyd werden mit 8.2 g. (205.7 mmol) Natriumhydrid (60%-ig in [PARaFFINoeL)] und 16.0 g [(150.] 9 mmol) [MERCAPTOESSIGSaeUREMETHYLESTER] 20.57 g eines Gemisches aus der Titelverbindung und der korrespondierenden Saeure (ca. 1 : 1) nach der allgemeinen Arbeitsvorschrift A erhalten. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With sodium hydroxide; In methanol; for 2h;Reflux; | The second step in the preparation of methyl 7-bromo-benzo [b] thiophene-2- carboxylate 64 mg (0.22 mmol) was dissolved in a 3 ml of methanol and then, 3N sodium hydroxide, 240 ul (0.72 mmol) was added 2 hours and heated to reflux. The reaction mixture was acidified with 3N hydrochloric acid and extracted with ethyl acetate 30 ml. It was charged and the organic dried and concentrated under reduced pressure over anhydrous sodium sulfate (Na2SO4). To give the 62 mg yield as a white solid target compound without a residue purified by silica gel column chromatography 100% (0.24 mmol). |
96% | General procedure: The solution of compound 2a or 2b (1.1 mmol) in water (10 mL)was stirred and then potassium hydroxide pellets (5.4 mmol) wasadded, which was refluxed for 3 h. The aqueous layer was thenacidified to pH 1 with 1 M hydrochloric acid solution. The aqueouslayer was extracted with dichloromethane (3 15 mL). The combinedorganic layers were dried with sodium sulfate, filtered, andthe solvents were removed under reduced pressure to afford thetitle compound 3a or 3b. | |
93% | With potassium hydroxide; In water; for 3h;Reflux; | General procedure: The solution of compound 2a-2n (1.1 mmol) in water (10 mL)was stirred and then potassium hydroxide pellets (5.4 mmol) wereadded, which was refluxed for 3 h. The aqueous layer was thenacidified to pH 1 with 1M hydrochloric acid solution. The aqueouslayer was extracted with dichloromethane (3 x 15 mL). The combinedorganic layers were dried with sodium sulfate, filtered, andthe solvents were removed under reduced pressure to afford thetitle compound 3a-3n [31,34]. |
91.0% | Ausgehend von 10.0 g (36.9 mmol) [7-BROM-L-BENZOTHIOPHEN-2-CARBONSaeUREMETHYL-] ester werden 8. [99 G] (91.0 % d. Th. ) des gewuenschten Produkts nach der allgemeinen Arbeitsvorschrift B erhalten. [H-NMR] (200 MHz, [DMSO-D6)] : [8] 13.76 (br. s, 1H), 8.28 [(S,] 1H), 8. [07] (d, 1H), 7.78 (d, 1H), 7.46 (dd, 1H). HPLC (Methode [1)] : Rt= 4.4 min. | |
272 mg | With lithium hydroxide monohydrate; In methanol; water; at 75℃; for 2h; | A mixture of 300 mg of methyl 7-bromobenzo[b]thiophene-2-carboxylate, 100 mg of lithium hydroxide monohydrate,3 ml of water, and 9 ml of methanol was stirred for 2 hours at 75C. The reaction mixture was concentratedunder reduced pressure. Water was added to the residues, and the residue was washed three times with tert-butylmethyl ether. Concentrated hydrochloric acid was added to the aqueous layer, and then extraction was performed threetimes by using tert-butyl methyl ether. The collected organic layer was washed with saturated saline, dried over magnesiumsulfate, and then concentrated under reduced pressure, thereby obtaining 272 mg of 7-bromobenzo[b]thiophene-2-carboxylic acid (hereinafter, described as a "compound 13 of the present invention"). 1H-NMR (DMSO-D6) delta: 13.74 (br s, 1H), 8.27 (s, 1H), 8.06 (dd, 1H, J = 7.8, 0.9 Hz), 7.78 (dd, 1H, J = 7.8, 0.9 Hz), 7.44(t, 1H, J = 7.8 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With diphenyl phosphoryl azide; N-ethyl-N,N-diisopropylamine; In water; N,N-dimethyl-formamide; at 0 - 8℃; | EXAMPLE 2 7-Bromo-1-benzothiophen-2-amine 156 mg (0.61 mmol) of <strong>[19075-59-3]7-bromo-1-benzothiophene-2-carboxylic acid</strong> are mixed with 156.8 mg (1.21 mmol) of N,N-diisopropylethylamine in 4.0 ml of DMF. At 0 C., 183.7 mg (0.67 mmol) of diphenyl phosphorazidate are added. The reaction mixture is left to stand at 8 C. overnight and then stirred into ice-water. It is neutralized with acetic acid, and the resulting precipitate is filtered off with suction and carefully dried at 40 C. The solid is then suspended in xylene and heated under reflux for 1 h. The solvent is removed under reduced pressure, and the residue is put in water and heated for 3 h. The aqueous phase is extracted several times with ethyl acetate. The organic phase is dried over sodium sulfate and then the solvent is removed under reduced pressure. 128 mg of the title compound are isolated in a purity which is suitable for further reactions. The amine is reacted further without further purification. LC-MS: Rt 5.25 min., MS (ESIpos): m/z=229 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With borane-THF; at 60℃; for 3h;Cooling with ice; | While cooled on ice, <strong>[19075-59-3]7-bromo-1-benzothiophene-2-carboxylic acid</strong> (0.52 g, 2.02 mmol) was added a little at a time to a 1.18 M borane-THF solution (6.86 mL, 8.10 mmol), and the mixture was then stirred for 3 hours at 60 C. The reaction solution was cooled on ice, 1 N hydrochloric acid was added to decompose the excess borane, and the mixture was then diluted with water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was then distilled off at reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) and recrystallized from hexane-ethyl acetate to give 0.41 g of the titled compound (yield 83%). Melting point: 82-83 C.1H NMR (CDCl3) delta: 1.94 (1H, t, J=6.0 Hz), 4.94 (2H, d, J=6.0 Hz), 7.21 (1H, d, J=7.8 Hz), 7.31 (1H, s), 7.47 (1H, d, J=7.8 Hz), 7.67 (1H, d, J=7.8 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | Ethyl 7-bromobenzo[b]thiophene-2-carboxylate (500.0 mg, 1.7 mmol), lithium hydroxide (250.0 mg, 10.4 mmol), tetrahydrofuran (6ml), and water (8 ml) were added to a 50-ml round-bottom flask and stirred at room temperature until the starting material was consumed as judged by thin layer chromatography analysis. The majority of the tetrahydrofuran was removed in vacuo. The resulting crude mixture was acidified with aqueous hydrochloric acid (pH 3) and cooled in an ice bath. The solids were filtered and washed with cold water (about 6 ml) to give the title compound (392 mg, 90%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | A mixture of <strong>[19075-59-3]7-bromobenzo[b]thiophene-2-carboxylic acid</strong> (25.6 mg, 0.1 mmol), (R)-tert-butyl3-aminopiperidine-1-carboxylate (24.0 mg, 0.12 mmol), N,Ndiisopropylethylamine (52 l, 0.3 mmol), and 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxidhexafluorophosphate (57.0 mg, 0.15 mmol) in dimethylformamide (2 ml) was stirred at room temperature for 12 h. The reaction mixture was diluted with ethyl acetate (15 ml) and washed with water (4 ml, 3). The organic layer was dried (MgSO4) and concentrated in vacuo. The crude residue was dissolved in CH2Cl2 (5 ml), trifluoroacetic acid (TFA) (5 ml) was added, and the reaction was stirred at room temperature for 1 h. The reaction was concentrated in vacuo to give a crude product, which was purified by reverse-phase preparative HPLC (A: methanol and acetonitrile (1:1, v/v); B: water containing TFA (0.1%, v/v)). The title compound was obtained as theTFA salt (31.6 mg, 70%). 1HNMR (CD3OD, 400 MHz) 8.10 (s,1H), 7.90 (dd, 1H, J0.8, 8.0 Hz), 7.63 (dd, 1H, J0.8, 7.6 Hz),7.36 (t, 1H, J8.0 Hz), 4.11 (m, 1H), 3.34 (m, 1H), 3.13 (m, 1H),2.74 (m, 2H), 2.08 (m, 1H), 1.69 (m, 2H). LC/MS (ESI) 339, 341(MH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With acetic acid; silver carbonate; In dimethyl sulfoxide; at 120℃; for 16h; | A mixture 3a or 4b (0.5 mmol), Ag2CO3 (0.05 mmol), AcOH(0.025 mmol) in DMSO (1.0 mL)was stirred at 120 C. After 16 h, thereactionwas cooled down to room temperature and quenched with1 M hydrochloric acid solution (2 mL) and the aqueous phaseextracted with ethyl acetate. The combined organic layers werewashed with brine and dried sodium sulfate, filtered, and the solventswere removed under reduced pressure to give analyticallypure 4a or 4b. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In N,N-dimethyl-formamide; at 20℃; | <strong>[19075-59-3]7-bromobenzo[b]thiophene-2-carboxylic acid</strong> (1 eq) was dissolved in DMF, to which morpholine (1.01 eq), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC, 1.1 eq), 1-hydroxybenzotriazole (HOBT, 1.1 eq), and TEA (3 eq)were added stepwise, followed by stirring at room temperature for overnight. The reaction was terminated with a smallamount of water, followed by extraction using water and EtOAc. The small amount of water remaining in the organiclayer was dried over anhydrous MgSO4. The solvent was eliminated by vacuum distillation, followed by vacuum drying.Then, a target compound was obtained by column separation with the yield of 48%. 1H NMR (300MHz, DMSO-d6) delta 7.95 (d, 1H), 7.90 (s, 1H), 7.70 (d, 1H), 3.66-3.65 (m, 8H). |
Tags: 19075-59-3 synthesis path| 19075-59-3 SDS| 19075-59-3 COA| 19075-59-3 purity| 19075-59-3 application| 19075-59-3 NMR| 19075-59-3 COA| 19075-59-3 structure
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H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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