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[ CAS No. 1370025-54-9 ] {[proInfo.proName]}

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Product Details of [ 1370025-54-9 ]

CAS No. :1370025-54-9 MDL No. :MFCD22056736
Formula : C8H6BrFO Boiling Point : -
Linear Structure Formula :- InChI Key :DQSGYGLIKSWXKJ-UHFFFAOYSA-N
M.W : 217.04 Pubchem ID :60155444
Synonyms :

Calculated chemistry of [ 1370025-54-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.45
TPSA : 17.07 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.82 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.87
Log Po/w (XLOGP3) : 2.54
Log Po/w (WLOGP) : 3.13
Log Po/w (MLOGP) : 2.94
Log Po/w (SILICOS-IT) : 3.53
Consensus Log Po/w : 2.8

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.12
Solubility : 0.163 mg/ml ; 0.000753 mol/l
Class : Soluble
Log S (Ali) : -2.55
Solubility : 0.618 mg/ml ; 0.00285 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.87
Solubility : 0.0291 mg/ml ; 0.000134 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.55

Safety of [ 1370025-54-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338-P304+P340-P405 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1370025-54-9 ]

* 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.

  • Downstream synthetic route of [ 1370025-54-9 ]

[ 1370025-54-9 ] Synthesis Path-Downstream   1~48

  • 1
  • [ 50-00-0 ]
  • [ 18349-09-2 ]
  • [ 1370025-54-9 ]
YieldReaction ConditionsOperation in experiment
38% Stage #1: 2-bromo-6-fluoro-4-methyl aniline With hydrogenchloride; sodium acetate; copper(II) sulfate; sodium sulfite; sodium nitrite In water at 0℃; Stage #2: formaldehyd With hydroxylamine hydrochloride; sodium acetate In water Stage #3: With hydrogenchloride In water Reflux;
  • 2
  • [ 1370025-54-9 ]
  • C10H10BrFO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium hexamethylsilazane / toluene 2: hydrogenchloride / water; acetone / Reflux 3: periodic acid; pyridinium chlorochromate / acetonitrile 4: hydrogenchloride / water / Reflux
  • 3
  • [ 1370025-54-9 ]
  • C11H11Br2FO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: potassium hexamethylsilazane / toluene 2: hydrogenchloride / water; acetone / Reflux 3: periodic acid; pyridinium chlorochromate / acetonitrile 4: hydrogenchloride / water / Reflux 5: lithium diisopropyl amide / tetrahydrofuran / -78 - -40 °C 6: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / Reflux
  • 4
  • [ 1370025-54-9 ]
  • C9H8BrFO [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hexamethylsilazane / toluene 2: hydrogenchloride / water; acetone / Reflux
  • 5
  • [ 1370025-54-9 ]
  • [ 1377934-85-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium hexamethylsilazane / toluene 2: hydrogenchloride / water; acetone / Reflux 3: periodic acid; pyridinium chlorochromate / acetonitrile
  • 6
  • [ 1370025-54-9 ]
  • [ 1377934-87-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium hexamethylsilazane / toluene 2: hydrogenchloride / water; acetone / Reflux 3: periodic acid; pyridinium chlorochromate / acetonitrile 4: hydrogenchloride / water / Reflux 5: lithium diisopropyl amide / tetrahydrofuran / -78 - -40 °C
  • 7
  • [ 1370025-54-9 ]
  • [ 1377934-89-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: potassium hexamethylsilazane / toluene 2.1: hydrogenchloride / water; acetone / Reflux 3.1: periodic acid; pyridinium chlorochromate / acetonitrile 4.1: hydrogenchloride / water / Reflux 5.1: lithium diisopropyl amide / tetrahydrofuran / -78 - -40 °C 6.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / Reflux 7.1: potassium carbonate / acetone / 0.25 h / 20 °C 7.2: 12 h / Reflux
  • 8
  • [ 1370025-54-9 ]
  • [ 1377934-90-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: potassium hexamethylsilazane / toluene 2.1: hydrogenchloride / water; acetone / Reflux 3.1: periodic acid; pyridinium chlorochromate / acetonitrile 4.1: hydrogenchloride / water / Reflux 5.1: lithium diisopropyl amide / tetrahydrofuran / -78 - -40 °C 6.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / Reflux 7.1: potassium carbonate / acetone / 0.25 h / 20 °C 7.2: 12 h / Reflux 8.1: hydrogenchloride; water; acetic acid / Reflux
  • 9
  • [ 1370025-54-9 ]
  • [ 1377934-91-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 1.1: potassium hexamethylsilazane / toluene 2.1: hydrogenchloride / water; acetone / Reflux 3.1: periodic acid; pyridinium chlorochromate / acetonitrile 4.1: hydrogenchloride / water / Reflux 5.1: lithium diisopropyl amide / tetrahydrofuran / -78 - -40 °C 6.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / Reflux 7.1: potassium carbonate / acetone / 0.25 h / 20 °C 7.2: 12 h / Reflux 8.1: hydrogenchloride; water; acetic acid / Reflux 9.1: dmap / 1,2-dichloro-ethane 10.1: trans-bromo(N-succinimidyl)-bis(triphenylphosphine)palladium(II); sodium carbonate / tetrahydrofuran; water / 3 h / Reflux 11.1: water; potassium hydroxide / ethanol / Reflux
  • 10
  • [ 1370025-54-9 ]
  • C16H18BrFO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: potassium hexamethylsilazane / toluene 2.1: hydrogenchloride / water; acetone / Reflux 3.1: periodic acid; pyridinium chlorochromate / acetonitrile 4.1: hydrogenchloride / water / Reflux 5.1: lithium diisopropyl amide / tetrahydrofuran / -78 - -40 °C 6.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / Reflux 7.1: potassium carbonate / acetone / 0.25 h / 20 °C 7.2: 12 h / Reflux 8.1: hydrogenchloride; water; acetic acid / Reflux 9.1: dmap / 1,2-dichloro-ethane
  • 11
  • [ 1370025-54-9 ]
  • C22H23FO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: potassium hexamethylsilazane / toluene 2.1: hydrogenchloride / water; acetone / Reflux 3.1: periodic acid; pyridinium chlorochromate / acetonitrile 4.1: hydrogenchloride / water / Reflux 5.1: lithium diisopropyl amide / tetrahydrofuran / -78 - -40 °C 6.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / Reflux 7.1: potassium carbonate / acetone / 0.25 h / 20 °C 7.2: 12 h / Reflux 8.1: hydrogenchloride; water; acetic acid / Reflux 9.1: dmap / 1,2-dichloro-ethane 10.1: trans-bromo(N-succinimidyl)-bis(triphenylphosphine)palladium(II); sodium carbonate / tetrahydrofuran; water / 3 h / Reflux
  • 12
  • [ 1370025-54-9 ]
  • [ 4009-98-7 ]
  • C10H10BrFO [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium hexamethylsilazane In toluene
YieldReaction ConditionsOperation in experiment
Stage #1: With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: In tetrahydrofuran for 1h; Inert atmosphere; 1 (1) Synthesis of compound 1a General procedure: Under nitrogen protection, m-bromofluorobenzene (1.000 g, 5.3 mmol) and 30 mL of anhydrous tetrahydrofuran (THF) were added to a dry 100 mL three-necked flask, Then the reaction flask was transferred to a low temperature reactor at -78°C, and after stirring for 30 minutes, 2.9 mL of lithium diisopropylamide (LDA, 2M in THF) was slowly added dropwise to the above reaction device, and after 30 minutes of reaction, 0.5 mL of anhydrous DMF was added dropwise to the above solution, and the reaction was continued for 1 h. After the reaction was completed, slowly drop 2 mL of saturated ammonium chloride solution into the above device to quench the reaction, then drop 5 mL of 0.5 mol/L HCl, and stir for another 15 minutes. After the reaction flask was removed from the low temperature reactor, 10 mL of 0.5 mol/L HCl was continued to be added, the solvent THF was removed by evaporation under reduced pressure, the residual mixture was extracted and separated with ethyl acetate (EA), and the collected organic phase was dried over anhydrous sodium sulfate. The drying agent was removed by filtration, and the concentrated filtrate was separated by column chromatography (petroleum ether) to obtain a white solid 1a.
  • 14
  • [ 1370025-54-9 ]
  • 4-bromo-6-methyl-1H-indazol-3-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium dodecyl-sulfate; [bis(acetoxy)iodo]benzene; ammonium acetate / water / 0.5 h / 70 °C 2: hydrazine hydrate / ethanol / 4 h / Reflux
Multi-step reaction with 2 steps 1: sodium dodecyl-sulfate; [bis(acetoxy)iodo]benzene; ammonium acetate / water / 0.5 h / 70 °C 2: hydrazine hydrate / ethanol / 4 h / Reflux
  • 15
  • [ 1370025-54-9 ]
  • tert-butyl 4-(10-bromo-8-methyl-2-oxo-1,2-dihydropyrimido[1,2-b]indazol-4-yl)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium dodecyl-sulfate; [bis(acetoxy)iodo]benzene; ammonium acetate / water / 0.5 h / 70 °C 2.1: hydrazine hydrate / ethanol / 4 h / Reflux 3.1: acetonitrile / 4 h / Reflux 3.2: 6 h / 70 °C
Multi-step reaction with 3 steps 1.1: sodium dodecyl-sulfate; [bis(acetoxy)iodo]benzene; ammonium acetate / water / 0.5 h / 70 °C 2.1: hydrazine hydrate / ethanol / 4 h / Reflux 3.1: acetonitrile / 4 h / Reflux 3.2: 6 h / 70 °C
  • 16
  • [ 202865-83-6 ]
  • [ 68-12-2 ]
  • [ 1370025-54-9 ]
YieldReaction ConditionsOperation in experiment
95% l-Bromo-3-fluoro-5-methylbenzene (5.00 g, 26.5 mmol) was dissolved in tetrahydrofuran (100 mL) and cooled to -78 C. Lithium diisopropyl amide (1.8 M in tetrahydrofuran, 16.2 mL, 29.1 mmol) was added. After stirring at -78 C for 30 min, N,N-dimethylformamide (2.32 g, 31.7 mmol) was added. After stirring at -78 C for an additional 15 min, acetic acid (6 mL) and water (100 mL) was added and the mixture was warmed to RT. After extraction with ethyl acetate, the organic phase was washed with 1 M hydrochloride acid solution and brine, and dried over magnesium sulfate. Concentration in vacuo afforded the title compound (5.45 g, 95% of theory). GC-MS (Method 1G): Rt = 4.39 min, MS (ESIPos): m/z = 217 [M+H]+
5.45 g Example 148A 2-Bromo-6-fluoro-4-methylbenzaldehyde 1-Bromo-3-fluoro-5-methylbenzene (5.00 g, 26.5 mmol) was dissolved in tetrahydrofuran (100 mL) and cooled to -78 C. Lithium diisopropyl amide (1.8 M in tetrahydrofuran, 16.2 mL, 29.1 mmol) was added. After stirring at -78 C. for 30 min, N,N-dimethylformamide (2.32 g, 31.7 mmol) was added. After stirring at -78 C. for an additional 15 min, acetic acid (6 mL) and water (100 mL) was added and the mixture was warmed to RT. After extraction with ethyl acetate, the organic phase was washed with 1 M hydrochloride acid solution and brine, and dried over magnesium sulfate. Concentration in vacuo afforded the title compound (5.45 g, 95% of theory). GC-MS (Method 1G): Rt=4.39 min, MS (ESIPos): m/z=217 [M+H]+
  • 17
  • [ 1370025-54-9 ]
  • [ 1023971-89-2 ]
YieldReaction ConditionsOperation in experiment
79% With [bis(acetoxy)iodo]benzene; ammonium acetate; sodium dodecyl-sulfate; In water; at 70℃; for 0.5h; A mixture of 2-bromo-6-fluoro-4-methylbenzaldehyde (5.45 g, 25.1 mmol), sodium lauryl sulfate (1.45 g, 5.03 mmol), (Diacetoxyiodo)benzene (12.1 g, 37.7 mmol) and ammonium acetate (9.68 g, 125.6 mmol) in water (25 mL) was stirred at 70 C for 30 min. After extraction with dichloromethane, the organic phase was dried over magnesium sulfate and concentrated in vacuo. Purification via preparative HPLC (Method 1A) afforded the title compound (4.26 g, 79% of theory). GC-MS (Method 1G): Rt = 4.43 min, MS (ESIPos): m/z = 215 [M+H]+
4.26 g With [bis(acetoxy)iodo]benzene; ammonium acetate; sodium dodecyl-sulfate; In water; at 70℃; for 0.5h; Example 149A 2-Bromo-6-fluoro-4-methylbenzonitrile A mixture of 2-bromo-6-fluoro-4-methylbenzaldehyde (5.45 g, 25.1 mmol), sodium lauryl sulfate (1.45 g, 5.03 mmol), (Diacetoxyiodo)benzene (12.1 g, 37.7 mmol) and ammonium acetate (9.68 g, 125.6 mmol) in water (25 mL) was stirred at 70 C. for 30 min After extraction with dichloromethane, the organic phase was dried over magnesium sulfate and concentrated in vacuo. Purification via preparative HPLC (Method 1A) afforded the title compound (4.26 g, 79% of theory). GC-MS (Method 1G): Rt=4.43 min, MS (ESIPos): m/z=215 [M+H]+
  • 18
  • [ 1370025-54-9 ]
  • 10-bromo-8-methyl-4-(piperidin-4-yl)pyrimido[1,2-b]indazol-2(1H)-one hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium dodecyl-sulfate; [bis(acetoxy)iodo]benzene; ammonium acetate / water / 0.5 h / 70 °C 2.1: hydrazine hydrate / ethanol / 4 h / Reflux 3.1: acetonitrile / 4 h / Reflux 3.2: 6 h / 70 °C 4.1: hydrogenchloride / 1,4-dioxane / 4 h / 20 °C
  • 19
  • [ 1370025-54-9 ]
  • [ 623-51-8 ]
  • ethyl 4-bromo-6-methylbenzo[b]thiophene-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 12h; Inert atmosphere; 31.4 Step 4) Synthesis of ethyl 4-bromo-6-methylbenzo[b]thiophene-2-carboxylate 2-Bromo-6-fluoro-4-methylbenzaldehyde (4.34 g, 20 mmol), potassium carbonate (5.53 g,40 mmol), ethyl 2-mercaptoacetate (2.88 g, 24 mmol) and N,N-dimethylformamide (40 mL) were added to a 100 mL single-neck flask. The resulting mixture was stirred at 80 °C for 12 h under nitrogen. The reaction mixture was cooled to room temperature and to the mixture was added saturated aqueous ammonium chloride (150 mL). The resulting mixture was extracted with ethyl acetate (100 mL x 2), and the organic layers were combined. The combined organic layers were washed with saturated brine (100 mL), dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated in vacuo. The residue was purified by silica-gel column chromatography (ethyl acetate/petroleum ether (v/v) = 1/100) to give the title compound as a white solid (5.09 g, 85%).‘H NIVIR (400 IVIFIz, CDC13) (ppm): 8.10 (s, 1H), 7.57 (s, 1H), 7.42 (s, 1H), 4.41 (q, J= 7.1 Hz, 2H), 2.46 (s, 3H), 1.42 (t, J= 7.1 Hz, 3H).
  • 20
  • [ 18349-09-2 ]
  • [ 1370025-54-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: hydrogenchloride; sodium nitrite / water; acetonitrile / 1 h / 0 °C 1.2: 0 - 20 °C 2.1: tetrahydrofuran / 1 h / -45 °C 2.2: 20 °C
  • 21
  • [ 452-80-2 ]
  • [ 1370025-54-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: acetic acid; bromine / methanol / 4.5 h / 0 - 20 °C 2.1: hydrogenchloride; sodium nitrite / water; acetonitrile / 1 h / 0 °C 2.2: 0 - 20 °C 3.1: tetrahydrofuran / 1 h / -45 °C 3.2: 20 °C
  • 22
  • [ 202865-83-6 ]
  • [ 1068-55-9 ]
  • [ 1370025-54-9 ]
YieldReaction ConditionsOperation in experiment
96% 1-Bromo-3-fluoro-5-methylbenzene (18.5 g, 58.7 mmol) and anhydrous tetrahydrofuran (250 mL) were added to a 500 mL single-neck flask, then to the mixture in flask was added dropwise slowly isopropylmagnesium chloride solution (35.2 mL, 2 M in THF) at -45 C. After the addition, the reaction mixture was stirred at -45 C for 1.0 h, then to the flask was added anhydrous N,N-dimethylformamide (17.2 g, 235 mmol). After the addition, the reaction mixture was warmed solwly to rt and stirred overnight. To the reaction mixture was added diluted hydrochloric acid (200 mL, 4 M), and the resulting mixture was stirred at rt for 2 h. The mixture was concentrated in vacuo to remove tetrahydrofuran. The residue was extracted with ethylacetate (100 mL x 2), and the organic layers were combined. The combined organic layers were washed with saturated brine (100 mL), dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated in vacuo. The residue was purified by silica-gel column chromatography (ethyl acetate/petroleum ether (v/v) = 1/200) to give the title compound as a light yellow solid(12.3 g, 96%).?HNMR (400 IVIHz, CDC13) (ppm): 10.31 (s, 1H), 7.31 (s, 1H), 6.95 (d, J 11.2 Hz, 1H), 2.39 (s, 3H).
  • 23
  • [ 1370025-54-9 ]
  • 4-(6-cyano-2-fluorobenzo[b]thiophen-4-yl)-2-hydroxybenzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 80 °C / Inert atmosphere 2.1: sodium hydroxide; water / methanol; tetrahydrofuran / 12 h / 20 °C 3.1: copper / quinoline / 0.5 h / 200 °C 4.1: 2-Methyl-2-nitropropane; N-hydroxyphthalimide; palladium diacetate / acetonitrile / 48 h / 80 °C 5.1: lithium diisopropyl amide / tetrahydrofuran / 1.5 h / -70 - 20 °C / Inert atmosphere 5.2: 12 h / 20 °C 6.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate / N,N-dimethyl-formamide; water / 0.5 h / 90 °C / Inert atmosphere 7.1: trifluoroacetic acid / dichloromethane / 12 h / 20 °C
  • 24
  • [ 1370025-54-9 ]
  • 4-bromo-2-fluorobenzo[b]thiophene-6-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 80 °C / Inert atmosphere 2.1: sodium hydroxide; water / methanol; tetrahydrofuran / 12 h / 20 °C 3.1: copper / quinoline / 0.5 h / 200 °C 4.1: 2-Methyl-2-nitropropane; N-hydroxyphthalimide; palladium diacetate / acetonitrile / 48 h / 80 °C 5.1: lithium diisopropyl amide / tetrahydrofuran / 1.5 h / -70 - 20 °C / Inert atmosphere 5.2: 12 h / 20 °C
  • 25
  • [ 1370025-54-9 ]
  • 4-bromobenzo[b]thiophene-6-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 80 °C / Inert atmosphere 2: sodium hydroxide; water / methanol; tetrahydrofuran / 12 h / 20 °C 3: copper / quinoline / 0.5 h / 200 °C 4: 2-Methyl-2-nitropropane; N-hydroxyphthalimide; palladium diacetate / acetonitrile / 48 h / 80 °C
  • 26
  • [ 1370025-54-9 ]
  • tert-butyl 4-(6-cyano-2-fluorobenzo[b]thiophene-4-yl)-2-hydroxybenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 80 °C / Inert atmosphere 2.1: sodium hydroxide; water / methanol; tetrahydrofuran / 12 h / 20 °C 3.1: copper / quinoline / 0.5 h / 200 °C 4.1: 2-Methyl-2-nitropropane; N-hydroxyphthalimide; palladium diacetate / acetonitrile / 48 h / 80 °C 5.1: lithium diisopropyl amide / tetrahydrofuran / 1.5 h / -70 - 20 °C / Inert atmosphere 5.2: 12 h / 20 °C 6.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate / N,N-dimethyl-formamide; water / 0.5 h / 90 °C / Inert atmosphere
  • 27
  • [ 1370025-54-9 ]
  • 4-(6-cyanobenzo[b]thiophen-4-yl)-2-hydroxybenzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 80 °C / Inert atmosphere 2: sodium hydroxide; water / methanol; tetrahydrofuran / 12 h / 20 °C 3: copper / quinoline / 0.5 h / 200 °C 4: 2-Methyl-2-nitropropane; N-hydroxyphthalimide; palladium diacetate / acetonitrile / 48 h / 80 °C 5: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate / N,N-dimethyl-formamide; water / 0.5 h / 90 °C / Inert atmosphere 6: trifluoroacetic acid / dichloromethane / 12 h / 20 °C
  • 28
  • [ 1370025-54-9 ]
  • 4-bromo-6-methylbenzo[b]thiophene-2-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 80 °C / Inert atmosphere 2: sodium hydroxide; water / methanol; tetrahydrofuran / 12 h / 20 °C
  • 29
  • [ 1370025-54-9 ]
  • [ 1427423-34-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 80 °C / Inert atmosphere 2: sodium hydroxide; water / methanol; tetrahydrofuran / 12 h / 20 °C 3: copper / quinoline / 0.5 h / 200 °C
  • 30
  • [ 1370025-54-9 ]
  • tert-butyl 4-(6-cyanobenzo[b]thiophen-4-yl)-2-hydroxybenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 80 °C / Inert atmosphere 2: sodium hydroxide; water / methanol; tetrahydrofuran / 12 h / 20 °C 3: copper / quinoline / 0.5 h / 200 °C 4: 2-Methyl-2-nitropropane; N-hydroxyphthalimide; palladium diacetate / acetonitrile / 48 h / 80 °C 5: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate / N,N-dimethyl-formamide; water / 0.5 h / 90 °C / Inert atmosphere
  • 31
  • [ 1370025-54-9 ]
  • 4-(2-chloro-6-cyanobenzo[b]thiophen-4-yl)-2-hydroxybenzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 80 °C / Inert atmosphere 2.1: sodium hydroxide; water / methanol; tetrahydrofuran / 12 h / 20 °C 3.1: copper / quinoline / 0.5 h / 200 °C 4.1: 2-Methyl-2-nitropropane; N-hydroxyphthalimide; palladium diacetate / acetonitrile / 48 h / 80 °C 5.1: lithium diisopropyl amide / tetrahydrofuran / 1.5 h / -70 °C 5.2: 20 °C 6.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate / N,N-dimethyl-formamide; water / 0.5 h / 90 °C / Inert atmosphere 7.1: trifluoroacetic acid / dichloromethane / 12 h / 20 °C
  • 32
  • [ 1370025-54-9 ]
  • 4-bromo-2-chlorobenzo[b]thiophene-6-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 80 °C / Inert atmosphere 2.1: sodium hydroxide; water / methanol; tetrahydrofuran / 12 h / 20 °C 3.1: copper / quinoline / 0.5 h / 200 °C 4.1: 2-Methyl-2-nitropropane; N-hydroxyphthalimide; palladium diacetate / acetonitrile / 48 h / 80 °C 5.1: lithium diisopropyl amide / tetrahydrofuran / 1.5 h / -70 °C 5.2: 20 °C
  • 33
  • [ 1370025-54-9 ]
  • tert-butyl 4-(2-chloro-6-cyanobenzo[b]thiophen-4-yl)-2-hydroxybenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 80 °C / Inert atmosphere 2.1: sodium hydroxide; water / methanol; tetrahydrofuran / 12 h / 20 °C 3.1: copper / quinoline / 0.5 h / 200 °C 4.1: 2-Methyl-2-nitropropane; N-hydroxyphthalimide; palladium diacetate / acetonitrile / 48 h / 80 °C 5.1: lithium diisopropyl amide / tetrahydrofuran / 1.5 h / -70 °C 5.2: 20 °C 6.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate / N,N-dimethyl-formamide; water / 0.5 h / 90 °C / Inert atmosphere
  • 34
  • [ 824-54-4 ]
  • [ 1370025-54-9 ]
YieldReaction ConditionsOperation in experiment
63% With 4-aminobenzene-1,3-disulfonic acid; palladium diacetate; 1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate at 110℃; for 24h; Sealed tube; regioselective reaction;
  • 35
  • [ 1370025-54-9 ]
  • [4-[[2-(tert-butoxycarbonylamino)-1-methylethyl]amino]-2-cyanobenzothiophen-6-yl]methyl acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2: ammonia / methanol / 110 °C 3: trifluoroacetic acid; pyridine / dichloromethane / 0.5 h / 25 °C 4: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 2 h / 90 °C 5: N,N-dimethyl-formamide / 1 h / 60 °C / Inert atmosphere 6: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / toluene / 3 h / 130 °C
  • 36
  • [ 1370025-54-9 ]
  • tert-butyl N-[2-[[2-(N-hydroxycarbamimidoyl)-6-(hydroxymethyl)benzothiophene-4-yl]amino]propyl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2: ammonia / methanol / 110 °C 3: trifluoroacetic acid; pyridine / dichloromethane / 0.5 h / 25 °C 4: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 2 h / 90 °C 5: N,N-dimethyl-formamide / 1 h / 60 °C / Inert atmosphere 6: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / toluene / 3 h / 130 °C 7: potassium carbonate; hydroxylamine hydrochloride / methanol / 1 h / 50 °C / Inert atmosphere
  • 37
  • [ 1370025-54-9 ]
  • tert-butyl N-[2-[[2-carbamimidoyl-6-(hydroxymethyl)-benzothiophen-4-yl]amino]propyl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2: ammonia / methanol / 110 °C 3: trifluoroacetic acid; pyridine / dichloromethane / 0.5 h / 25 °C 4: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 2 h / 90 °C 5: N,N-dimethyl-formamide / 1 h / 60 °C / Inert atmosphere 6: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / toluene / 3 h / 130 °C 7: potassium carbonate; hydroxylamine hydrochloride / methanol / 1 h / 50 °C / Inert atmosphere 8: acetic acid; hydrogen / methanol / 1 h / 40 °C
  • 38
  • [ 1370025-54-9 ]
  • tert-butyl N-[4-[[2-(tert-butoxycarbonylamino)-1-methylethyl] amino]-6-(hydroxymethyl)ben zothiophene-2-carboximidoyl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2: ammonia / methanol / 110 °C 3: trifluoroacetic acid; pyridine / dichloromethane / 0.5 h / 25 °C 4: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 2 h / 90 °C 5: N,N-dimethyl-formamide / 1 h / 60 °C / Inert atmosphere 6: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / toluene / 3 h / 130 °C 7: potassium carbonate; hydroxylamine hydrochloride / methanol / 1 h / 50 °C / Inert atmosphere 8: acetic acid; hydrogen / methanol / 1 h / 40 °C 9: triethylamine; dmap / N,N-dimethyl-formamide / 4 h / 20 °C
  • 39
  • [ 1370025-54-9 ]
  • [4-[[2-(tert-butoxycarbonylamino)-1-methylethyl]amino]-2-(N-tert-butoxycarbonylcarbamimidoyl)benzothiophen-6-yl]methyl methanesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2: ammonia / methanol / 110 °C 3: trifluoroacetic acid; pyridine / dichloromethane / 0.5 h / 25 °C 4: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 2 h / 90 °C 5: N,N-dimethyl-formamide / 1 h / 60 °C / Inert atmosphere 6: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / toluene / 3 h / 130 °C 7: potassium carbonate; hydroxylamine hydrochloride / methanol / 1 h / 50 °C / Inert atmosphere 8: acetic acid; hydrogen / methanol / 1 h / 40 °C 9: triethylamine; dmap / N,N-dimethyl-formamide / 4 h / 20 °C 10: triethylamine / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere
  • 40
  • [ 1370025-54-9 ]
  • S-[[4-[[2-(tert-butoxycarbonylamino)-1-methylethyl]amino]-2-(N-tert-butoxycarbonylcarbamimidoyl)benzothiophen-6-yl]methyl]ethanethioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2: ammonia / methanol / 110 °C 3: trifluoroacetic acid; pyridine / dichloromethane / 0.5 h / 25 °C 4: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 2 h / 90 °C 5: N,N-dimethyl-formamide / 1 h / 60 °C / Inert atmosphere 6: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / toluene / 3 h / 130 °C 7: potassium carbonate; hydroxylamine hydrochloride / methanol / 1 h / 50 °C / Inert atmosphere 8: acetic acid; hydrogen / methanol / 1 h / 40 °C 9: triethylamine; dmap / N,N-dimethyl-formamide / 4 h / 20 °C 10: triethylamine / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere 11: N,N-dimethyl-formamide / 1 h / 20 °C
  • 41
  • [ 1370025-54-9 ]
  • S-[[4-[(2-amino-1-methylethyl)amino]-2-carbamimidoylbenzothiophen-6-yl]methyl] ethanethioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 12 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2: ammonia / methanol / 110 °C 3: trifluoroacetic acid; pyridine / dichloromethane / 0.5 h / 25 °C 4: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 2 h / 90 °C 5: N,N-dimethyl-formamide / 1 h / 60 °C / Inert atmosphere 6: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / toluene / 3 h / 130 °C 7: potassium carbonate; hydroxylamine hydrochloride / methanol / 1 h / 50 °C / Inert atmosphere 8: acetic acid; hydrogen / methanol / 1 h / 40 °C 9: triethylamine; dmap / N,N-dimethyl-formamide / 4 h / 20 °C 10: triethylamine / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere 11: N,N-dimethyl-formamide / 1 h / 20 °C 12: trifluoroacetic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere
  • 42
  • [ 1370025-54-9 ]
  • 4-[(2-amino-1-methylethyl)amino]-6-[[[4-[(2-amino-1-methylethyl)amino]-2-carbamimidoylbenzothiophen-6-yl]-methyldisulfanyl]methyl]benzothiophene-2-carboxamidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 13 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2: ammonia / methanol / 110 °C 3: trifluoroacetic acid; pyridine / dichloromethane / 0.5 h / 25 °C 4: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 2 h / 90 °C 5: N,N-dimethyl-formamide / 1 h / 60 °C / Inert atmosphere 6: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / toluene / 3 h / 130 °C 7: potassium carbonate; hydroxylamine hydrochloride / methanol / 1 h / 50 °C / Inert atmosphere 8: acetic acid; hydrogen / methanol / 1 h / 40 °C 9: triethylamine; dmap / N,N-dimethyl-formamide / 4 h / 20 °C 10: triethylamine / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere 11: N,N-dimethyl-formamide / 1 h / 20 °C 12: trifluoroacetic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere 13: potassium carbonate / 1 h / 20 °C
  • 43
  • [ 1370025-54-9 ]
  • 4-[(2-amino-1-methylethyl)amino]-6-(sulfanylmethyl)-benzothiophene-2-carboxamidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 14 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2: ammonia / methanol / 110 °C 3: trifluoroacetic acid; pyridine / dichloromethane / 0.5 h / 25 °C 4: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 2 h / 90 °C 5: N,N-dimethyl-formamide / 1 h / 60 °C / Inert atmosphere 6: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / toluene / 3 h / 130 °C 7: potassium carbonate; hydroxylamine hydrochloride / methanol / 1 h / 50 °C / Inert atmosphere 8: acetic acid; hydrogen / methanol / 1 h / 40 °C 9: triethylamine; dmap / N,N-dimethyl-formamide / 4 h / 20 °C 10: triethylamine / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere 11: N,N-dimethyl-formamide / 1 h / 20 °C 12: trifluoroacetic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere 13: potassium carbonate / 1 h / 20 °C 14: trimethylphosphane / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere
  • 45
  • [ 1370025-54-9 ]
  • 4-bromo-6-methylbenzothiophene-2-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2: ammonia / methanol / 110 °C 3: trifluoroacetic acid; pyridine / dichloromethane / 0.5 h / 25 °C
  • 46
  • [ 1370025-54-9 ]
  • 4-bromo-6-(bromomethyl)benzothiophene-2-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2: ammonia / methanol / 110 °C 3: trifluoroacetic acid; pyridine / dichloromethane / 0.5 h / 25 °C 4: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 2 h / 90 °C
  • 47
  • [ 1370025-54-9 ]
  • (4-bromo-2-cyanobenzothiophen-6-yl)methyl acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2: ammonia / methanol / 110 °C 3: trifluoroacetic acid; pyridine / dichloromethane / 0.5 h / 25 °C 4: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 2 h / 90 °C 5: N,N-dimethyl-formamide / 1 h / 60 °C / Inert atmosphere
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