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CAS No. : | 98800-10-3 | MDL No. : | MFCD01934498 |
Formula : | C8H6O2S2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VCLNJFSCOKHCEJ-UHFFFAOYSA-N |
M.W : | 198.26 | Pubchem ID : | 2739788 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 8 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 50.98 |
TPSA : | 82.78 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.45 cm/s |
Log Po/w (iLOGP) : | 2.38 |
Log Po/w (XLOGP3) : | 2.9 |
Log Po/w (WLOGP) : | 2.75 |
Log Po/w (MLOGP) : | 1.95 |
Log Po/w (SILICOS-IT) : | 4.14 |
Consensus Log Po/w : | 2.82 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.26 |
Solubility : | 0.11 mg/ml ; 0.000553 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.3 |
Solubility : | 0.00996 mg/ml ; 0.0000502 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -2.69 |
Solubility : | 0.403 mg/ml ; 0.00203 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.48 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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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 |
---|---|---|
83% | With triethylamine In dimethyl sulfoxide; ethyl acetate | Thieno[3,2-b]thiophene-2-carboxamidine hydrochloride Methyl 2-(2-formylthien-3-ylthio)ethanoate (47.8 mg, 0.22 mmol) and triethylamine (0.20 g, 2 mmol) were heated in DMSO (2 mL) under N2 with stirring for 2 h. The reaction mixture was diluted with ether (30 mL), and was washed with dilute HCl (1M, 10 mL), water (2*10 mL), and saturated brine (10 mL), and dried (MgSO4). The solvent was removed under reduced pressure, and the residue was purified by preparative tlc on silica (10% EtOAc in hexanes) to give methyl thieno[3,2-b]thiophene-2-carboxylate (36.2 mg, 83%) as a crystalline solid mp 96°-7° C. |
36.93 g | With piperidine; acetic acid In benzene for 5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With sulfuric acid; In water; at 0℃; for 8h;Reflux; | 500 mg (2.7 mmol, 1.0 eq) of <strong>[1723-27-9]thieno [3,2-B] thiophene-2-carboxylic acid</strong> (Compound 12-1) was added to methanol 5.0 ml, cooled to 0 C,Concentrated sulfuric acid (265 mg, 2.7 mmol, l.Oeq)After the addition was complete, the reaction was warmed to room temperature and then heated to reflux overnight.TLC raw materials are surplus,The reaction was cooled to 0 C,Supplemented with concentrated sulfuric acid (530 mg, 5.4 mmol, 2.0 eq)Then heated to reflux for 8 hours, TLC reaction completely.The reaction solution was cooled to room temperature, poured into about 50 ml of ice water, stirred for 20 minutes, filtered and the filter cake was rinsed with water and dried to give the product as yellowish solid compound 12-2 (504 mg, yield 94%Directly for the next reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With sodium hydride In N,N-dimethyl-formamide for 3h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.8% | With lithium aluminium tetrahydride In tetrahydrofuran at -30 - 20℃; for 1h; Inert atmosphere; | 12 Lithium aluminium hydride (474 mg, 12.48 mmol, 1.5 eq)Was suspended in dry THF (5.0 ml), protected with nitrogen,To a solution of 1.65 g (8.32 mmol, 1. Oeq) of thieno [3,2-B] thiophene-2-carboxylate in THF (10 ml) was cooled to -30 ° C., Slowly dropwise added to the reaction solution, after dropping slowly warming to room temperature for 1 hour, TLC reaction completely. After the reaction was cooled to -20 ° C, EA was slowly added dropwise to produce no bubbles, then 20% aqueous solution of sodium hydroxide was added dropwise to form a loose precipitate; the filter cake was rinsed well with EA; the filtrate was saturated with chlorinated Ammonium chloride solution 2 times, washed 1 times, brine washed 1 times, anhydrous sodium sulfate drying, filtration, the filtrate was concentrated to dry in crude.15 ml of n-hexane was added to the crude product and the mixture was beaten for 30 minutes. The filter cake was concentrated under reduced pressure to give compound 12-3, 1.29 g, yield 90.8%. |
90% | With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; for 5h; | |
77.6% | With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere; | 6B; XIII Example 6-B Under nitrogen, compound 3 (300 g, 1.52 mol) dissolved in anhydrous THF (2500 mL) was added dropwise to a mixture of LiAlH4 (75 g, 1.98 mol) in anhydrous THF (1500 mL) at 0° C. After the addition, the mixture was stirred at rt for 2 hs and compound 3 was consumed completely. Cooled to 0° C., water (75 mL) was added dropwise followed by the addition of 10% NaOH aq. (125 mL) dropwise. The mixture was filtered and the cake was washed with DCM several times. The filtration was concentrated under reduced pressure to give compound 4 (258 g, 77.6%) as a white solid. |
With lithium aluminium tetrahydride In diethyl ether for 3h; Ambient temperature; Yield given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 92.5 percent / NaOAc / acetic acid / 0.5 h / Heating 2: 93 g / 8 percent NaOH / 0.5 h / 45 - 60 °C 3: Cl2 / 1,1,2-trichloro-ethane / 1.) RT, 1 h, 2.) reflux, 1 h 4: 400 g / HCl / 2 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 62 percent / NaH / dimethylformamide / 3 h / Ambient temperature 2: 1.) acetic anhydride, 98 percent formic acid, 2.) NaIO4 / 1.) 65 deg C, 30 min, 2.) from 65 deg C to 55 deg C, 20 min 3: 1 N NaOH / methanol / 0.5 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 62 percent / NaH / dimethylformamide / 3 h / Ambient temperature 2: 1.) acetic anhydride, 98 percent formic acid, 2.) NaIO4 / 1.) 65 deg C, 30 min, 2.) from 65 deg C to 55 deg C, 20 min |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 62 percent / NaH / dimethylformamide / 3 h / Ambient temperature 2: 1.) acetic anhydride, 98 percent formic acid, 2.) NaIO4 / 1.) 65 deg C, 30 min, 2.) from 65 deg C to 55 deg C, 20 min 3: 1 N NaOH / methanol / 0.5 h / Ambient temperature 4: 1 g / NaOH / methanol / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 62 percent / NaH / dimethylformamide / 3 h / Ambient temperature 2: 1.) acetic anhydride, 98 percent formic acid, 2.) NaIO4 / 1.) 65 deg C, 30 min, 2.) from 65 deg C to 55 deg C, 20 min 3: 1 N NaOH / methanol / 0.5 h / Ambient temperature 4: 1 g / NaOH / methanol / Ambient temperature 5: oxalyl chloride / dimethylformamide; acetonitrile / 2 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 62 percent / NaH / dimethylformamide / 3 h / Ambient temperature 2: 1.) acetic anhydride, 98 percent formic acid, 2.) NaIO4 / 1.) 65 deg C, 30 min, 2.) from 65 deg C to 55 deg C, 20 min 3: 1 N NaOH / methanol / 0.5 h / Ambient temperature 4: 1 g / NaOH / methanol / Ambient temperature 5: oxalyl chloride / dimethylformamide; acetonitrile / 2 h / 0 °C 6: 1.5 g / BSTFA / acetonitrile / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: 62 percent / NaH / dimethylformamide / 3 h / Ambient temperature 2: 1.) acetic anhydride, 98 percent formic acid, 2.) NaIO4 / 1.) 65 deg C, 30 min, 2.) from 65 deg C to 55 deg C, 20 min 3: 1 N NaOH / methanol / 0.5 h / Ambient temperature 4: 1 g / NaOH / methanol / Ambient temperature 5: oxalyl chloride / dimethylformamide; acetonitrile / 2 h / 0 °C 6: 1.5 g / BSTFA / acetonitrile / 0 - 20 °C 7: 50 percent HCOOH, zinc / methanol / 2 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: 62 percent / NaH / dimethylformamide / 3 h / Ambient temperature 2: 1.) acetic anhydride, 98 percent formic acid, 2.) NaIO4 / 1.) 65 deg C, 30 min, 2.) from 65 deg C to 55 deg C, 20 min 3: 1 N NaOH / methanol / 0.5 h / Ambient temperature 4: 1 g / NaOH / methanol / Ambient temperature 5: oxalyl chloride / dimethylformamide; acetonitrile / 2 h / 0 °C 6: 1.5 g / BSTFA / acetonitrile / 0 - 20 °C 7: 50 percent HCOOH, zinc / methanol / 2 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 93 g / 8 percent NaOH / 0.5 h / 45 - 60 °C 2: Cl2 / 1,1,2-trichloro-ethane / 1.) RT, 1 h, 2.) reflux, 1 h 3: 400 g / HCl / 2 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Cl2 / 1,1,2-trichloro-ethane / 1.) RT, 1 h, 2.) reflux, 1 h 2: 400 g / HCl / 2 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 17.6 g / pyridinium tosylate / toluene / 1 h / Heating 3: p-toluenesulfonic acid hydrate / acetone / 1 h 4: 36.93 g / piperidine, acetic acid / benzene / 5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 2: p-toluenesulfonic acid hydrate / acetone / 1 h 3: 36.93 g / piperidine, acetic acid / benzene / 5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: LiAlH4 / diethyl ether / 3 h / Ambient temperature 2: 23.30 g / pyridinium chlorochromate / CH2Cl2 / 2.5 h | ||
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / diethyl ether / 5 h / 0 - 20 °C 2: pyridinium chlorochromate / dichloromethane / 2.5 h / 20 °C | ||
Multi-step reaction with 3 steps 1: lithium hydroxide; water / tetrahydrofuran / 4 h / 100 °C 2: copper(l) iodide; N,N,N,N,-tetramethylethylenediamine / 1-methyl-pyrrolidin-2-one / 1 h / 220 °C 3: trichlorophosphate / 12 h / 25 - 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: LiAlH4 / diethyl ether / 3 h / Ambient temperature 2: 23.30 g / pyridinium chlorochromate / CH2Cl2 / 2.5 h 3: pyridinium tosylate / benzene / 4 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: LiAlH4 / diethyl ether / 3 h / Ambient temperature 2: 23.30 g / pyridinium chlorochromate / CH2Cl2 / 2.5 h 3: pyridinium tosylate / benzene / 4 h / Heating 5: concd. NH4OH / acetone / 0.75 h / 0 - 10 °C 6: 91 percent / p-toluenesulfonic acid monohydrate / acetone / 5 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: LiAlH4 / diethyl ether / 3 h / Ambient temperature 2: 23.30 g / pyridinium chlorochromate / CH2Cl2 / 2.5 h 3: pyridinium tosylate / benzene / 4 h / Heating 5: concd. NH4OH / acetone / 0.75 h / 0 - 10 °C 6: 91 percent / p-toluenesulfonic acid monohydrate / acetone / 5 h / Ambient temperature 7: HCl / methanol / 0.08 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: LiAlH4 / diethyl ether / 3 h / Ambient temperature 2: 23.30 g / pyridinium chlorochromate / CH2Cl2 / 2.5 h 3: pyridinium tosylate / benzene / 4 h / Heating 5: concd. NH4OH / acetone / 0.75 h / 0 - 10 °C 6: 91 percent / p-toluenesulfonic acid monohydrate / acetone / 5 h / Ambient temperature 7: HCl / methanol / 0.08 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: LiAlH4 / diethyl ether / 3 h / Ambient temperature 2: 23.30 g / pyridinium chlorochromate / CH2Cl2 / 2.5 h 3: pyridinium tosylate / benzene / 4 h / Heating 5: concd. NH4OH / acetone / 0.75 h / 0 - 10 °C 6: 91 percent / p-toluenesulfonic acid monohydrate / acetone / 5 h / Ambient temperature 7: HCl / methanol / 0.08 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: LiAlH4 / diethyl ether / 3 h / Ambient temperature 2: 23.30 g / pyridinium chlorochromate / CH2Cl2 / 2.5 h 3: pyridinium tosylate / benzene / 4 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: LiAlH4 / diethyl ether / 3 h / Ambient temperature 2: 23.30 g / pyridinium chlorochromate / CH2Cl2 / 2.5 h 3: pyridinium tosylate / benzene / 4 h / Heating 5: concd. NH4OH / acetone / 0.75 h / 0 - 10 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: LiAlH4 / diethyl ether / 3 h / Ambient temperature 2: 23.30 g / pyridinium chlorochromate / CH2Cl2 / 2.5 h 3: pyridinium tosylate / benzene / 4 h / Heating 5: concd. NH4OH / acetone / 0.75 h / 0 - 10 °C 6: 91 percent / p-toluenesulfonic acid monohydrate / acetone / 5 h / Ambient temperature 7: 1.) HCl, 2b.) 4 A sieves / 1.) methanol, 10 min, 2a.) 24 h, 2b.) 6 d |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: LiAlH4 / diethyl ether / 3 h / Ambient temperature 2: 23.30 g / pyridinium chlorochromate / CH2Cl2 / 2.5 h 3: pyridinium tosylate / benzene / 4 h / Heating 5: concd. NH4OH / acetone / 0.75 h / 0 - 10 °C 6: 91 percent / p-toluenesulfonic acid monohydrate / acetone / 5 h / Ambient temperature 7: HCl / methanol / 0.08 h / Heating 8: NaBH4 / methanol; tetrahydrofuran / 0.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: LiAlH4 / diethyl ether / 3 h / Ambient temperature 2: 23.30 g / pyridinium chlorochromate / CH2Cl2 / 2.5 h 3: pyridinium tosylate / benzene / 4 h / Heating 5: concd. NH4OH / acetone / 0.75 h / 0 - 10 °C 6: 91 percent / p-toluenesulfonic acid monohydrate / acetone / 5 h / Ambient temperature 7: HCl / methanol / 0.08 h / Heating 8: NaBH4 / methanol; tetrahydrofuran / 0.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: LiAlH4 / diethyl ether / 3 h / Ambient temperature 2: 23.30 g / pyridinium chlorochromate / CH2Cl2 / 2.5 h 3: pyridinium tosylate / benzene / 4 h / Heating 5: concd. NH4OH / acetone / 0.75 h / 0 - 10 °C 6: 91 percent / p-toluenesulfonic acid monohydrate / acetone / 5 h / Ambient temperature 7: HCl / methanol / 0.08 h / Heating 8: NaBH4 / methanol; tetrahydrofuran / 0.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: LiAlH4 / diethyl ether / 3 h / Ambient temperature 2: 23.30 g / pyridinium chlorochromate / CH2Cl2 / 2.5 h 3: pyridinium tosylate / benzene / 4 h / Heating 5: concd. NH4OH / acetone / 0.75 h / 0 - 10 °C 6: 91 percent / p-toluenesulfonic acid monohydrate / acetone / 5 h / Ambient temperature 7: 1.) HCl, 2b.) 4 A sieves / 1.) methanol, 10 min, 2a.) 24 h, 2b.) 6 d 8: NaCNBH3 / methanol / 48 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: p-toluenesulfonic acid hydrate / acetone / 1 h 2: 36.93 g / piperidine, acetic acid / benzene / 5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: tin (IV)-chloride; carbon disulfide 2: potassium hexacyanoferrate(III); aqueous KOH-solution 3: diethyl ether | ||
Multi-step reaction with 3 steps 1.1: trichlorophosphate / 1,2-dichloro-ethane / 48 h / 90 °C / Cooling with ice 1.2: Cooling with ice 2.1: 2-methyl-but-2-ene; sodium chlorite; sodium dihydrogenphosphate dihydrate / water; tetrahydrofuran; <i>tert</i>-butyl alcohol / 20 °C / Cooling with ice 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 20 °C 3.2: 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate; acetic acid In water; toluene; benzene | 1.E Methyl thieno[3,2-b]thiophene-2-carboxylate (6) STR9 Step E Methyl thieno[3,2-b]thiophene-2-carboxylate (6) STR9 Piperidine (37.9 g., 445 mmoles) was added to a solution of acetic acid (26.7 g., 445 mmole) in benzene (1 L) and stirred for 5 minutes. Methyl 2-formylthiophen-3-yl-3-thiapropionate (5) (96.91 g., 448 mmoles) was added in benzene to a total volume of benzene (2.2 L). The solution was refluxed while stirring and water was collected via a Dean-Stark trap. After 5 hours of reflux, 7.8 ml of water was collected. The mixture was cooled to room temperature and extracted with water two times, then 1N.HCl followed by water, and then by a saturated solution of sodium bicarbonate two times. The resulting benzene solution was dried (MgSO4), filtered and evaporated to leave 88 g. of crude product. This was extracted with room temperature ether, then three times with boiling ether, leaving a tarry gum. Silica gel (100 g.) was added to the ether solution of the product. The solvent was evaporated and the clumps broken up leaving a free flowing product adsorbed on silica gel. This was chromatographed on silica gel eluding with 50% hexane in toluene. The solvent was evaporated from the fractions containing the product and after trituration with hexane, 36.93 g. of methyl thieno[3,2-b]thiophene-2-carboxylate (6), mp 96°-97° C. was isolated. Calc. for C8 H6 O2 S2: C, 48.47; H, 3.05; Found: C, 48.85; H, 3.14. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | Stage #1: picoline; methyl thieno<3,2-b>thiophene-2-carboxylate With lithium hexamethyldisilazane In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Stage #2: With hydrogenchloride In water Stage #3: <i>N</i>,<i>N</i>-dimethyl-formamide dimethyl acetal | 4-[3-(3-Thieno[3,2-b]thiophen-2-yl)-lH-pyrazol-4-yl]pyridineTo a solution of 4-methylpyridine (1 eq, 22.6 mmol) and methyl 3-thieno[3,2-b]thiophene-2 carboxylate (1.12 eq, 25.3 mmol) in anhydrous tetrahydroiurane (20 mL) at 0 °C, under N2 was added dropwise a solution of lithium bis(trimethylsilyl)amide (1 molar solution in tetrahydrofurane, 2 eq, 45.1 mmol). The mixture was stirred 3 h at 5 °C and overnight at room temperature. The resulting precipitate was filtered, washed with diisopropylether and dried to afford a yellow solid (7.4g).This solid was dissolved in 150 mL of water and a 1M solution of hydrochloric acid was carefully added until pH reached 5. The resulting precipitated was filtered and dried to afford a green solid (5.3g). This solid was dissolved in Ν,Ν-dimethylformamide dimethylacetal (30 mL). The mixture was refluxed for 1 h. The solvant was evaporated. The residue was purified by colomn chromatography on silica gel (ethyl acetate) to afford 3.8 g of a brown solid.This solid was dissolved in 80 mL of absolute ethanol and hydrazine hydrate (17.2 mmol) and triethylamine (17.2 mmol) were added. The resulting mixture was stirred at reflux for 3 h. The solvant was then evaporated and the residue was suspended in 50 mL of ethanol. The resulting precipitate was filtered and dried to afford 2.8 g of 4-[3-(3-thieno[3,2-b]thiophen-2-yl)-lH-pyrazol- 4-yl]pyridine (44% yield).'H-NMR (400 MHz, dg-DMSO): δ = 13.42 (bs, 1H), 8.56 (d, 2H), 8.23 (s, 1H), 7.67 (d, 1H), 7.45 (m, 3H), 7.37 (s, lH) ppm |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82.6% | With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 5h; | To a mixture of compound 1 (350 g, 1.83 mol) and K2CO3 (1000 g, 7.33 mol) in DMF (4000 mL) was added compound 2 (195 g, 1.83 mol) at rt. The resultant mixture was stirred at 70 C. for 5 hs. After cooled to rt, the mixture was poured into ice-water and solids were precipitated out which was obtained by filtration and dried in vacuo at 50 C. to give compound 3 (300 g, 82.6%) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: lithium aluminium tetrahydride / diethyl ether / 5 h / 0 - 20 °C 2: pyridinium chlorochromate / dichloromethane / 2.5 h / 20 °C 3: sodium hydrogencarbonate; bromine / chloroform / 2 h / 0 - 20 °C 4: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 1 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: lithium aluminium tetrahydride / diethyl ether / 5 h / 0 - 20 °C 2: pyridinium chlorochromate / dichloromethane / 2.5 h / 20 °C 3: sodium hydrogencarbonate; bromine / chloroform / 2 h / 0 - 20 °C 4: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 1 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: lithium aluminium tetrahydride / diethyl ether / 5 h / 0 - 20 °C 2: pyridinium chlorochromate / dichloromethane / 2.5 h / 20 °C 3: sodium hydrogencarbonate; bromine / chloroform / 2 h / 0 - 20 °C 4: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; 1,2-dimethoxyethane / 4 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: lithium aluminium tetrahydride / diethyl ether / 5 h / 0 - 20 °C 2: pyridinium chlorochromate / dichloromethane / 2.5 h / 20 °C 3: sodium hydrogencarbonate; bromine / chloroform / 2 h / 0 - 20 °C 4: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 2 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: lithium aluminium tetrahydride / diethyl ether / 5 h / 0 - 20 °C 2: pyridinium chlorochromate / dichloromethane / 2.5 h / 20 °C 3: sodium hydrogencarbonate; bromine / chloroform / 2 h / 0 - 20 °C 4: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 2 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: lithium aluminium tetrahydride / diethyl ether / 5 h / 0 - 20 °C 2: pyridinium chlorochromate / dichloromethane / 2.5 h / 20 °C 3: sodium hydrogencarbonate; bromine / chloroform / 2 h / 0 - 20 °C 4: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 1 h / Inert atmosphere; Reflux 5: piperidine / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With iodine; bis-[(trifluoroacetoxy)iodo]benzene In tetrachloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: lithium hydroxide; water / tetrahydrofuran / 4 h / 100 °C 2: copper(l) iodide; N,N,N,N,-tetramethylethylenediamine / 1-methyl-pyrrolidin-2-one / 1 h / 220 °C 3: trichlorophosphate / 12 h / 25 - 60 °C 4: aluminum oxide / dichloromethane / 12 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: lithium hydroxide; water / tetrahydrofuran / 4 h / 100 °C 2: copper(l) iodide; N,N,N,N,-tetramethylethylenediamine / 1-methyl-pyrrolidin-2-one / 1 h / 220 °C 3: N,N-dimethyl-formamide / 12 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: lithium hydroxide; water / tetrahydrofuran / 4 h / 100 °C 2: copper(l) iodide; N,N,N,N,-tetramethylethylenediamine / 1-methyl-pyrrolidin-2-one / 1 h / 220 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: lithium hydroxide; water / tetrahydrofuran / 4 h / 100 °C 2: copper(l) iodide; N,N,N,N,-tetramethylethylenediamine / 1-methyl-pyrrolidin-2-one / 1 h / 220 °C 3: trichlorophosphate / 12 h / 25 - 60 °C 4: aluminum oxide / dichloromethane / 12 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: lithium hydroxide; water / tetrahydrofuran / 4 h / 100 °C 2: copper(l) iodide; N,N,N,N,-tetramethylethylenediamine / 1-methyl-pyrrolidin-2-one / 1 h / 220 °C 3: trichlorophosphate / 12 h / 25 - 60 °C 4: aluminum oxide / dichloromethane / 12 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: lithium hydroxide; water / tetrahydrofuran / 4 h / 100 °C 2: copper(l) iodide; N,N,N,N,-tetramethylethylenediamine / 1-methyl-pyrrolidin-2-one / 1 h / 220 °C 3: trichlorophosphate / 12 h / 25 - 60 °C 4: aluminum oxide / dichloromethane / 12 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: lithium hydroxide; water / tetrahydrofuran / 4 h / 100 °C 2: copper(l) iodide; N,N,N,N,-tetramethylethylenediamine / 1-methyl-pyrrolidin-2-one / 1 h / 220 °C 3: trichlorophosphate / 12 h / 25 - 60 °C 4: aluminum oxide / dichloromethane / 12 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: methyl thieno<3,2-b>thiophene-2-carboxylate With 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex In tetrahydrofuran; toluene at -60℃; for 1h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; toluene at -60 - 20℃; | 3-Iodothieno[3,2-b]thiophene-2-carboxylic acid 3-Iodothieno[3,2-b]thiophene-2-carboxylic acid Under an argon atmosphere, methyl thieno[3,2-b]thiophene-2-carboxylate (5.00 g, 25.2 mmol) was dissolved in 20 ml of dry tetrahydrofuran. The solution was cooled to -60° C. and tetramethylpiperidinemagnesium chloride lithium chloride complex (6.11 g, 25.2 mmol, dissolved 1M in toluene/tetrahydrofuran) was slowly added dropwise. After 1 h of stirring at -60° C., iodine (6.40 g, 25.2 mmol, dissolved in 10 ml of tetrahydrofuran) was added dropwise. The mixture was slowly warmed to room temperature and 200 ml of saturated ammonium chloride solution were added. The organic phase was separated off, the solvent was removed on a rotary evaporator and the crude product methyl 3-iodothieno[3,2-b]thiophene-2-carboxylate was used directly for the subsequent reaction. Methyl 3-iodothieno[3,2-b]thiophene-2-carboxylate (8.1 g, 25 mmol) was dissolved in 100 ml of THF, and lithium hydroxide (2.99 g, 125 mmol) in 20 ml of water was added. The reaction mixture was stirred vigorously at room temperature for 12 h. The mixture was neutralized with 1N hydrochloric acid, and water was added. A precipitate (3-iodothieno[3,2-b]thiophene-2-carboxylic acid) formed, which was isolated by filtration. |
Tags: 98800-10-3 synthesis path| 98800-10-3 SDS| 98800-10-3 COA| 98800-10-3 purity| 98800-10-3 application| 98800-10-3 NMR| 98800-10-3 COA| 98800-10-3 structure
[ 201004-08-2 ]
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