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[ CAS No. 3133-78-6 ] {[proInfo.proName]}

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Quality Control of [ 3133-78-6 ]

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Product Details of [ 3133-78-6 ]

CAS No. :3133-78-6 MDL No. :MFCD01830305
Formula : C10H8O2S Boiling Point : -
Linear Structure Formula :- InChI Key :YVKLUKXESFJRCE-UHFFFAOYSA-N
M.W : 192.23 Pubchem ID :821868
Synonyms :

Calculated chemistry of [ 3133-78-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.1
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 53.75
TPSA : 65.54 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) : -5.23 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.79
Log Po/w (XLOGP3) : 3.16
Log Po/w (WLOGP) : 2.91
Log Po/w (MLOGP) : 2.26
Log Po/w (SILICOS-IT) : 3.46
Consensus Log Po/w : 2.71

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.85

Water Solubility

Log S (ESOL) : -3.47
Solubility : 0.0653 mg/ml ; 0.00034 mol/l
Class : Soluble
Log S (Ali) : -4.21
Solubility : 0.0119 mg/ml ; 0.0000621 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -3.11
Solubility : 0.151 mg/ml ; 0.000783 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.01

Safety of [ 3133-78-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H302-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 3133-78-6 ]

* 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 [ 3133-78-6 ]

[ 3133-78-6 ] Synthesis Path-Downstream   1~100

  • 1
  • [ 1455-18-1 ]
  • [ 3133-78-6 ]
YieldReaction ConditionsOperation in experiment
With n-butyllithium; diethyl ether Behandeln des Reaktionsgemisches mit festem Kohlendioxid;
Multi-step reaction with 2 steps 1: tetrachloromethane; bromine / Behandeln des Reaktionsprodukts mit wss. Kalilauge 2: magnesium; diethyl ether / anschliessend Behandeln mit Kohlendioxid
  • 2
  • [ 5381-23-7 ]
  • [ 3133-78-6 ]
YieldReaction ConditionsOperation in experiment
With diethyl ether; magnesium anschliessend Behandeln mit Kohlendioxid;
  • 3
  • [ 3216-47-5 ]
  • [ 3133-78-6 ]
YieldReaction ConditionsOperation in experiment
With diethyl ether; magnesium anschliessend Behandlung mit Chlorokohlensaeure-aethylester und Hydrolyse des Reaktionsprodukts;
Multi-step reaction with 3 steps 1: amalgamated magnesium; diethyl ether / Behandeln unter Stickstoff dieser Benzo<<i>b</i>>thiophen-3-yl-methylmagnesium-chlorid-Loesung mit Eis und wss. Ammoniumchlorid-Loesung 2: tetrachloromethane; bromine / Behandeln des Reaktionsprodukts mit wss. Kalilauge 3: magnesium; diethyl ether / anschliessend Behandeln mit Kohlendioxid
Multi-step reaction with 3 steps 1: dioxane; tin (II)-chloride; concentrated aqueous HCl 2: tetrachloromethane; bromine / Behandeln des Reaktionsprodukts mit wss. Kalilauge 3: magnesium; diethyl ether / anschliessend Behandeln mit Kohlendioxid
  • 4
  • [ 3133-78-6 ]
  • [ 1455-18-1 ]
YieldReaction ConditionsOperation in experiment
100% With acetic acid; silver carbonate In dimethyl sulfoxide at 120℃; for 16h;
89% With copper(l) iodide; triethylamine In dimethyl sulfoxide at 140℃; for 20h; Inert atmosphere; Schlenk technique;
With quinoline; copper oxide-chromium oxide at 170℃;
  • 5
  • [ 3133-78-6 ]
  • [ 3133-88-8 ]
YieldReaction ConditionsOperation in experiment
With lithium aluminium tetrahydride; diethyl ether
  • 6
  • [ 875257-99-1 ]
  • [ 3133-78-6 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide at 120℃;
  • 7
  • [ 3216-47-5 ]
  • [ 3133-78-6 ]
YieldReaction ConditionsOperation in experiment
With diethyl ether; magnesium Behandeln des Reaktionsgemisches mit Kohlendioxid;
  • 8
  • [ 3133-78-6 ]
  • 3-Methyl-2,3-dihydro-benzo[b]thiophene-2-carboxylic acid (1R,3R,5S)-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Na/Hg, KOH, H2O / 4 h / Ambient temperature 2: SOCl2 / 5 h / 60 °C 3: benzene / 12 h / Heating
  • 9
  • [ 2142-68-9 ]
  • [ 68-11-1 ]
  • [ 3133-78-6 ]
YieldReaction ConditionsOperation in experiment
27% With potassium hydroxide; nitrogen; tetrabutylammomium bromide In water 5 Example 5 Example 5 Preparation of 3-methyl-2-benzo[b]thiophenecarboxylic acid Potassium hydroxide (12.5 g) was dissolved in water (105 ml) in a glass pressure bottle cooled in an ice bath. Then under a blanket of nitrogen, thioglycolic acid (7 ml) was added to the glass pressure bottle, to produce a reaction mixture. 2'-chloroacetophenone (12 g, 97%, 0.075 mol) and TBAB (0.5 g) were then added to the reaction mixture. The glass pressure bottle was then sealed and heated to 253° F. for 6 hours at 18 psi. The reaction was shut down and left overnight. Heating was then resumed at 270° F. at 30 psi for six hours and then cooled to ambient temperature. After the bottle was opened, the reaction mixture was washed with ether to remove organics, and acidified with hydrochloric acid to give 3.9 g of crude 3-methyl 2-benzo[b]thiophenecarboxylic acid (27% yield, mp>200° C.).
  • 10
  • [ 3133-78-6 ]
  • [ 75-65-0 ]
  • [ 1104395-30-3 ]
YieldReaction ConditionsOperation in experiment
83% With diphenylphosphoranyl azide; N-ethyl-N,N-diisopropylamine for 8h; Reflux; 5.A Example 5 A. 3-Methylbenzo[b]thiophen-2-yl-carbamic acid tert-butyl ester (5b). A solution of 2-carboxy-3-methylbenzo[b]thiophene (10.25 g, 53.3 mmol), N,N-diisopropylethylamine (10.2 mL, 58.6 mmol) and diphenylphosphoryl azide (12.7 mL, 58.6 mmol) in t-butanol (120 mL) was heated at reflux for 8 hours. The solvent was evaporated in vacuo, and the residue partitioned between DCM and saturated aqueous sodium bicarbonate. The organic layer was separated, dried over magnesium sulfate, filtered, and the solvent was evaporated in vacuo. The residue was purified by flash column chromatography on silica gel, using dichloromethane as the eluant, to give Compound 5b as a colorless solid (11.6 g, 83%).
53% With diphenyl phosphoryl azide; N-ethyl-N,N-diisopropylamine for 8h; Heating / reflux; 4 Example 4125-D Compound 125 a)DPPA, DIEA, J-BuOH; b) NaH, 3,4-difluorobenzyl bromide, DMF; c) TFA, DCM; d) benzenesulfonyl chloride, DMAP, pyridine.(3-Methyl-benzo[Z>]thiophen-2-yl)-carbamic acid tert-butyl ester (125-B); A solution of compound 125-A (3.15 g, 16.4 mmol), N,N-diisopropylethylamine (3.15 mL, 18.0 mmol) and diphenyl phosphoryl azide (4.23 mL, 19.7 mmol) in J-butanol (40 mL) was heated at reflux for 8 h. The solvent was evaporated in vacuo, and the residue partitioned between dichloromethane and IN aqueous sodium hydroxide. The organic layer was applied to a silica gel column, and the product isolated by flash column chromatography eluting with an ethyl acetate-heptane gradient, to afford compound 125-B as a colorless solid (2.3 g, 53%). 1H-NMR (CDCl3): δ 1.48 (s, 9H), 2.26 (s, 3H), 6.74 (br s, IH), 7.21-7.26 (m, IH), 7.31-7.36 (m, IH), 7.54 (d, IH), 7.71 (d, IH); MS: m/z 264.1 (MH+).
53% With diphenyl phosphoryl azide; N-ethyl-N,N-diisopropylamine for 8h; Reflux; 4 Example 4 (3-methyl-benzo[b]thiophen-2-yl)-carbamic acid tert-butyl ester (125-B) A solution of compound 125-A (3.15 g, 16.4 mmol), N,N-diisopropylethylamine (3.15 mL, 18.0 mmol) and diphenyl phosphoryl azide (4.23 mL, 19.7 mmol) in t-butanol (40 mL) was heated at reflux for 8 h. The solvent was evaporated in vacuo, and the residue partitioned between dichloromethane and 1N aqueous sodium hydroxide. The organic layer was applied to a silica gel column, and the product isolated by flash column chromatography eluting with an ethyl acetate-heptane gradient, to afford compound 125-B as a colorless solid (2.3 g, 53%). 1H-NMR (CDCl3): δ 1.48 (s, 9H), 2.26 (s, 3H), 6.74 (br s, 1H), 7.21-7.26 (m, 1H), 7.31-7.36 (m, 1H), 7.54 (d, 1H), 7.71 (d, 1H); MS: m/z 264.1 (MH+).
With diphenylphosphoranyl azide; N-ethyl-N,N-diisopropylamine In toluene Reflux; 1.A; 6.A Example 1 A. tert-Butyl-3-methylbenzo[b]thiophen-2-ylcarbamate (1-B). A 5-L 4-neck flask equipped with an overhead mechanical stirrer, N2 inlet/outlet adapter, reflux condenser, heating mantle and thermocouple was charged with t-butyl alcohol (2.11 L), compound 1-A (225.0 g, 1.17 mol), and diisopropylethylamine (225 mL, 1.29 mol). Diphenylphosphorylazide (304 mL, 1.4 mol) was premixed with toluene (300 mL) and then added drop-wise over 10 min. The reaction mixture was refluxed with stirring for 21 h, cooled to 22° C. and then evaporated in vacuo. The residue was dissolved in CH2Cl2 (1 L), washed with 1N NaOH (500 mL), brine (500 mL), the organic layer separated, dried over MgSO4, filtered, and evaporated in vacuo to afford a dark orange oil (557 g). The crude residue was purified by the flash column chromatography (SiO2) eluting with heptane-EtOAc to afford 265 g of compound 1-B as a pale yellow solid. 1H-NMR (CDCl3): δ 7.71 (d, 1H), 7.54 (d, 1H), 7.36-7.31 (m, 1H), 7.30-7.20 (m, 1H), 6.75 (br s, 1H), 2.23 (s, 3H), 1.55 (s, 9H).

  • 11
  • [ 3133-78-6 ]
  • [ 4129-17-3 ]
  • [ 1104395-30-3 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In dichloromethane; toluene; <i>tert</i>-butyl alcohol 1.A STEP A: STEP A: tert-Butyl-3-methylbenzo[b]thiophen-2-ylcarbamate A 5-L 4-neck flask equipped with an overhead mechanical stirrer, N2 inlet/outlet adapter, reflux condenser, heating mantle and thermocouple was charged with t-butyl alcohol (2.11 L), 3-methyl-benzo[b]thiophene-2-carboxylic acid (225.0 g, 1.17 mol), and diisopropylethylamine (225 mL, 1.29 mol). Diphenylphosphorylazide (304 mL, 1.4 mol) was premixed with toluene (300 mL) and then added drop-wise over 10 min. The resulting mixture was refluxed with stirring for 21 h, cooled to 22° C. and then evaporated in vacuo. The resulting residue was dissolved in CH2Cl2 (1 L), washed with 1 N NaOH (500 mL), brine (500 mL), the organic layer separated, dried over MgSO4, filtered, and evaporated in vacuo to yield a dark orange oil (557 g). The oil was purified by the flash column chromatography (SiO2) eluding with heptane-EtOAc to yield tert-butyl-3-methylbenzo[b]thiophen-2-ylcarbamate as a pale yellow solid. 1H-NMR (CDCl3) δ 7.71 (d, 1H), 7.54 (d, 1H), 7.36-7.31 (m, 1H), 7.30-7.20 (m, 1H), 6.75 (br s,1H), 2.23 (s, 3H), 1.55 (s, 9H).
  • 12
  • [ 3133-78-6 ]
  • C26H33N3O3 [ No CAS ]
  • C36H39N3O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In dichloromethane at 20℃; for 18h;
  • 13
  • [ 79-24-3 ]
  • [ 3133-78-6 ]
  • [ 1242462-20-9 ]
YieldReaction ConditionsOperation in experiment
67% With palladium(II) trifluoroacetate; dimethyl sulfoxide; silver carbonate; Trimethylacetic acid In 1,4-dioxane at 110℃; for 24h; Inert atmosphere;
  • 14
  • [ 3133-78-6 ]
  • [ 1121057-75-7 ]
  • [ 1251537-36-6 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20℃; Example 5: Tetrahydropyridine 5 was prepared in 2 steps starting with the deprotection of 1 usingMethod 3. The resulting HCl amine salt was dissolved in 7V,7V-dimethylformamide (0.2 M). 3- Methyl-l-benzothiophene-2-carboxylic acid (1.0 equiv) and PyBOP (1.0 equiv) were added followed by the dropwise addition of triethylamine (3.0 equiv). After stirring at room temperature for 30 min, the reaction was diluted with water and filtered. The isolated material was then purified using semi -preparatory liquid chromatography to isolate the fraction of desired boronic acid 5 that resulted from pinacol ester deprotection during the course of the acid coupling. [M-H]- = 300.1 m/z. Activity: B
  • 15
  • [ 3133-78-6 ]
  • [ 1455-18-1 ]
  • [ 1258844-19-7 ]
YieldReaction ConditionsOperation in experiment
64% With palladium(II) trifluoroacetate; silver carbonate In dimethyl sulfoxide; N,N-dimethyl-formamide at 130℃; for 16h; Inert atmosphere;
  • 16
  • [ 3133-78-6 ]
  • [ 292638-85-8 ]
  • [ 1253180-93-6 ]
YieldReaction ConditionsOperation in experiment
72% With oxygen; palladium diacetate In dimethyl sulfoxide; N,N-dimethyl-formamide at 120℃; for 10h; optical yield given as %de; diastereoselective reaction;
  • 17
  • [ 3133-78-6 ]
  • [ 75-05-8 ]
  • [ 18781-31-2 ]
YieldReaction ConditionsOperation in experiment
51% Stage #1: 3-methylbenzo[b]thiophene-2-carboxylic acid; acetonitrile With palladium(II) trifluoroacetate; 6-methyl-2,2'-bipyridine In water at 130℃; for 1h; Microwave irradiation; Stage #2: With formic acid In water at 100℃; for 1h;
  • 18
  • [ 67-56-1 ]
  • [ 3133-78-6 ]
  • [ 3133-81-1 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride for 4h; Reflux; 1.a a) 3-Methyl-benzo[b]thiophene-2-carboxylic acid methyl ester Thionyl chloride (15 g, 26 mmol) was added to methanol (100 ml), and 3-methyl-benzo[b]thiophene-2-carboxylic acid (5 g, 26.0 mmol) was dissolved, refluxed for 4 hours, and then evaporated to obtain a target compound 3-methyl-benzo[b]thiophene-2-carboxylic acid methyl ester (5.10 g, 24.7 mmol).
  • 19
  • [ 3133-78-6 ]
  • [ 372-38-3 ]
  • [ 1263757-42-1 ]
YieldReaction ConditionsOperation in experiment
52% With potassium phosphate; palladium(II) trifluoroacetate; silver carbonate; tricyclohexylphosphine In 1,4-dioxane; dimethyl sulfoxide at 140℃; for 22h; Molecular sieve; Inert atmosphere;
  • 20
  • [ 3133-78-6 ]
  • [ 363-72-4 ]
  • [ 1263757-12-5 ]
YieldReaction ConditionsOperation in experiment
92% With potassium phosphate; palladium(II) trifluoroacetate; silver carbonate; tricyclohexylphosphine In 1,4-dioxane; dimethyl sulfoxide at 140℃; for 22h; Molecular sieve; Inert atmosphere;
  • 21
  • [ 3133-78-6 ]
  • [ 85068-35-5 ]
  • [ 1263757-46-5 ]
YieldReaction ConditionsOperation in experiment
55% With potassium phosphate; palladium(II) trifluoroacetate; silver carbonate; tricyclohexylphosphine In 1,4-dioxane; dimethyl sulfoxide at 140℃; for 22h; Molecular sieve; Inert atmosphere;
  • 22
  • [ 3133-78-6 ]
  • methyl 3,5-difluorobenzoate [ No CAS ]
  • [ 1263757-48-7 ]
YieldReaction ConditionsOperation in experiment
61% With potassium phosphate; palladium(II) trifluoroacetate; silver carbonate; tricyclohexylphosphine In 1,4-dioxane; dimethyl sulfoxide at 140℃; for 22h; Molecular sieve; Inert atmosphere;
  • 23
  • [ 3133-78-6 ]
  • [ 29540-83-8 ]
  • [ 1276113-97-3 ]
YieldReaction ConditionsOperation in experiment
82% With (1,10-phenanthroline)bis(triphenylphosphine)copper(I) nitrate; potassium <i>tert</i>-butylate; palladium diacetate In 1-methyl-pyrrolidin-2-one at 170℃; for 1h; Sonication; Continuous flow reactor;
  • 24
  • [ 3133-78-6 ]
  • [ 1312551-98-6 ]
YieldReaction ConditionsOperation in experiment
85% With potassium <i>tert</i>-butylate In ethanol at 20℃; for 1h; Inert atmosphere;
With potassium <i>tert</i>-butylate In ethanol at 20℃; for 3h; Inert atmosphere;
  • 25
  • [ 3133-78-6 ]
  • [ 1338563-32-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 4-methyl-morpholine; HATU / dichloromethane / 20 °C 2: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 20 °C
  • 26
  • [ 3133-78-6 ]
  • [ 1338563-33-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 4-methyl-morpholine; HATU / dichloromethane / 20 °C 2: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 20 °C 3: 4-methyl-morpholine; HATU / dichloromethane / 20 °C
  • 27
  • [ 3133-78-6 ]
  • [ 1338562-83-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 4-methyl-morpholine; HATU / dichloromethane / 20 °C 2: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 20 °C 3: 4-methyl-morpholine; HATU / dichloromethane / 20 °C 4: hydrogenchloride / 1,4-dioxane; tetrahydrofuran / 1.5 h / 20 °C
  • 28
  • [ 3133-78-6 ]
  • [ 1029720-98-6 ]
  • [ 1338563-30-6 ]
YieldReaction ConditionsOperation in experiment
With 4-methyl-morpholine; HATU In dichloromethane at 20℃; 13.1 To a mixture of ethyl 4,5,6,7-tetrandropyrazolo[1,5-a]pyrazine-2-carboxylate (0.029 g, 0.15 mmol) and 3-methylbenzo[b]thiophene-2-carboxylic acid (0.0314 g, 0.163 mmol) in methylene chloride (1.5 mL) was added N,N,N',N'-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (0.0678 g, 0.178 mmol) and N-methylmorpholine (0.05 mL, 0.446 mmol). The reaction mixture was stirred at room temperature overnight. The reaction was diluted with additional methylene chloride (1.5 mL) and was washed with aqueous NaHCO3 (2 mL). The layers were separated and the aqueous layer was extracted with additional methylene chloride (3 mL) and the combined organic layers evaporated to dryness to give crude ethyl 5-(3-methylbenzo[b]thiophene-2-carbonyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate Intermediate 23.
  • 29
  • [ 96-43-5 ]
  • [ 3133-78-6 ]
  • [ 1356488-34-0 ]
YieldReaction ConditionsOperation in experiment
82% With palladium(II) trifluoroacetate; silver carbonate; tricyclohexylphosphine In 1,4-dioxane; dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere;
  • 30
  • [ 1455-18-1 ]
  • [ 124-38-9 ]
  • [ 3133-78-6 ]
YieldReaction ConditionsOperation in experiment
95% With 2,3,6,7-tetramethoxy-9(10H)-anthracenone; caesium carbonate In dimethyl sulfoxide at 25℃; for 18h; Irradiation; Sealed tube; regioselective reaction; General Procedure for the Carboxylation of Hetero(arenes) and Styrenes- GP2a General procedure: To a dry flat-bottomed crimp vial (5 mL) equipped with stirring bar, was added the arene (if solid)(0.1 mmol) and 2,3,6,7-tetramethoxyanthracen-9(10H)-one (6.3 mg, 0.02 mmol, 20 mol %). Cs2CO3 (98 mg,3 equiv.) was quickly added and the vial was sealed with a Supelco aluminium crimp seal with septum(PTFE/butyl). The vial was then evacuated and refilled with CO2 (5×) via syringe needle. The reactionmixture was dissolved in DMSO (1 mL, dry and degassed by bubbling with N2) and the arene (0.1 mmol) (ifliquid) was added via syringe. The vial was sealed with two layers of Parafilm and then had gaseous CO2added via a Luer Lock Monoject (20 ccm) syringe, into the head space. The vial was then irradiated fromthe bottom side with blue LED light and a constant reaction temperature (25°C) was maintained byemploying a water-cooling circuit connected to a thermostat. After 18 hrs of reaction time the pressure wasreleased. For product isolation, the reaction mixtures of 4 reactions run in parallel were combined andtransferred with water and Et2O into a separating funnel. The ether layer was extracted with water (3×) andthe combined aqueous layers were acidified with aq. HCl (2M) to adjust to an acidic pH. The aqueous layerwas extracted with EtOAc (3×) and the combined EtOAc layers were dried over Na2SO4, filtered andconcentrated in vacuo. The crude material was purified by silica flash column chromatography usingmixtures of hexanes and ethyl acetate with 0.5% HOAc (v/v) as eluents.
81% With ethylaluminum dichloride In hexane; toluene at 100℃; for 3h; Autoclave; Inert atmosphere; regioselective reaction;
  • 31
  • [ 129931-45-9 ]
  • [ 3133-78-6 ]
  • [ 1393456-21-7 ]
YieldReaction ConditionsOperation in experiment
52% With dichloro bis(acetonitrile) palladium(II); silver carbonate; tricyclohexylphosphine In 1,2-dimethoxyethane; dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere;
  • 32
  • [ 3133-78-6 ]
  • [ 2516-96-3 ]
  • [ 1393456-18-2 ]
YieldReaction ConditionsOperation in experiment
74% With dichloro bis(acetonitrile) palladium(II); silver carbonate; tricyclohexylphosphine In 1,2-dimethoxyethane; dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere;
  • 33
  • [ 3133-78-6 ]
  • [ 1882-69-5 ]
  • [ 1393456-17-1 ]
YieldReaction ConditionsOperation in experiment
62% With palladium(II) trifluoroacetic acid; silver carbonate; tricyclohexylphosphine In 1,2-dimethoxyethane; dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere;
  • 34
  • [ 3133-78-6 ]
  • [ 552-16-9 ]
  • [ 1393456-09-1 ]
YieldReaction ConditionsOperation in experiment
81% With palladium(II) trifluoroacetic acid; silver carbonate; tricyclohexylphosphine In 1,2-dimethoxyethane; dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere;
  • 35
  • [ 3133-78-6 ]
  • [ 7304-32-7 ]
  • [ 1393456-20-6 ]
YieldReaction ConditionsOperation in experiment
67% With dichloro bis(acetonitrile) palladium(II); silver carbonate; tricyclohexylphosphine In 1,2-dimethoxyethane; dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere;
  • 36
  • [ 3133-78-6 ]
  • [ 99-60-5 ]
  • [ 1393456-19-3 ]
YieldReaction ConditionsOperation in experiment
71% With dichloro bis(acetonitrile) palladium(II); silver carbonate; tricyclohexylphosphine In 1,2-dimethoxyethane; dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere;
  • 37
  • [ 3133-78-6 ]
  • [ 3113-72-2 ]
  • [ 1393456-15-9 ]
YieldReaction ConditionsOperation in experiment
82% With palladium(II) trifluoroacetic acid; silver carbonate; tricyclohexylphosphine In 1,2-dimethoxyethane; dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere;
  • 38
  • [ 3133-78-6 ]
  • [ 320-94-5 ]
  • [ 1393456-13-7 ]
  • 39
  • [ 3133-78-6 ]
  • [ 6280-88-2 ]
  • [ 1393456-11-5 ]
YieldReaction ConditionsOperation in experiment
68% With dichloro bis(acetonitrile) palladium(II); silver carbonate; tricyclohexylphosphine In 1,2-dimethoxyethane; dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere;
  • 40
  • [ 3133-78-6 ]
  • [ 33844-21-2 ]
  • [ 1393456-16-0 ]
  • 41
  • [ 3133-78-6 ]
  • [ 91-52-1 ]
  • [ 1393456-35-3 ]
YieldReaction ConditionsOperation in experiment
44% With dichloro bis(acetonitrile) palladium(II); silver carbonate; tricyclohexylphosphine In 1,2-dimethoxyethane; dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere;
  • 42
  • [ 3133-78-6 ]
  • [ 1466-76-8 ]
  • [ 1356488-13-5 ]
YieldReaction ConditionsOperation in experiment
51% With dichloro bis(acetonitrile) palladium(II); silver carbonate; tricyclohexylphosphine In 1,2-dimethoxyethane; dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere;
  • 43
  • [ 3133-78-6 ]
  • [ 99277-71-1 ]
  • [ 1393456-12-6 ]
YieldReaction ConditionsOperation in experiment
60% With dichloro bis(acetonitrile) palladium(II); silver carbonate; tricyclohexylphosphine In 1,2-dimethoxyethane; dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere;
  • 44
  • [ 3133-78-6 ]
  • [ 27329-27-7 ]
  • [ 1393456-14-8 ]
  • 45
  • [ 3133-78-6 ]
  • [ 394-01-4 ]
  • [ 1393456-10-4 ]
  • 46
  • [ 3133-78-6 ]
  • [ 93-55-0 ]
  • C18H14OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With copper diacetate; palladium diacetate; Tetrabutylammonium hydrogen diacetate; tricyclohexylphosphine In 1,2-dimethoxyethane at 110℃; for 24h; Inert atmosphere;
  • 47
  • [ 3133-78-6 ]
  • [ 1104630-85-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine; diphenyl phosphoryl azide / 8 h / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C 2.2: 2 h / 20 °C
  • 48
  • [ 3133-78-6 ]
  • [ 1104623-99-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine; diphenyl phosphoryl azide / 8 h / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C 2.2: 2 h / 20 °C 3.1: trifluoroacetic acid / dichloromethane / 4 h / 20 °C
  • 49
  • [ 3133-78-6 ]
  • [ 1104623-01-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine; diphenyl phosphoryl azide / 8 h / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C 2.2: 2 h / 20 °C 3.1: trifluoroacetic acid / dichloromethane / 4 h / 20 °C 4.1: pyridine / dmap / 0 - 20 °C
  • 50
  • [ 3133-78-6 ]
  • [ 3163-27-7 ]
  • [ 1415968-16-9 ]
YieldReaction ConditionsOperation in experiment
103 mg Stage #1: 3-methylbenzo[b]thiophene-2-carboxylic acid With lithium diisopropyl amide In tetrahydrofuran at -10℃; for 0.5h; Inert atmosphere; Stage #2: 2-(bromomethyl)naphthalene In tetrahydrofuran at -10 - 20℃; Inert atmosphere;
  • 51
  • [ 3133-78-6 ]
  • [ 13686-49-2 ]
  • [ 1415968-17-0 ]
YieldReaction ConditionsOperation in experiment
78 mg Stage #1: 3-methylbenzo[b]thiophene-2-carboxylic acid With lithium diisopropyl amide In tetrahydrofuran at -10℃; for 0.5h; Inert atmosphere; Stage #2: 1-(2-bromo)ethylnaphthalene In tetrahydrofuran at -10 - 20℃; Inert atmosphere;
  • 52
  • [ 3133-78-6 ]
  • [ 13247-79-5 ]
  • [ 1415968-18-1 ]
YieldReaction ConditionsOperation in experiment
101 mg Stage #1: 3-methylbenzo[b]thiophene-2-carboxylic acid With lithium diisopropyl amide In tetrahydrofuran at -10℃; for 0.5h; Inert atmosphere; Stage #2: 1-(2-bromoethoxy)naphthalene In tetrahydrofuran at -10 - 20℃; Inert atmosphere;
101 mg Stage #1: 3-methylbenzo[b]thiophene-2-carboxylic acid With lithium diisopropyl amide In tetrahydrofuran at -10℃; for 0.5h; Inert atmosphere; Stage #2: 1-(2-bromoethoxy)naphthalene In tetrahydrofuran at -10 - 20℃; for 16h; Inert atmosphere;
  • 53
  • [ 3133-78-6 ]
  • [ 26583-62-0 ]
  • [ 1415968-53-4 ]
YieldReaction ConditionsOperation in experiment
89 mg Stage #1: 3-methylbenzo[b]thiophene-2-carboxylic acid With lithium diisopropyl amide In tetrahydrofuran at -10℃; for 0.5h; Inert atmosphere; Stage #2: 5-(2-bromoethoxy)-2-chloro-1,3-dimethylbenzene In tetrahydrofuran at -10 - 20℃; Inert atmosphere;
  • 54
  • [ 3133-78-6 ]
  • [ 59508-09-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium <i>tert</i>-butylate / ethanol / 3 h / 20 °C / Inert atmosphere 2: bis(dibenzylideneacetone)-palladium(0); copper(I) oxide; 3,4,7,8-Tetramethyl-o-phenanthrolin; 2-(2-(dicyclohexylphosphino)phenyl)-5,6-dimethyl-1-octyl-1H-benzo[d]imidazole / 1-methyl-pyrrolidin-2-one; 1,3,5-trimethyl-benzene / 0.58 h / 50 - 180 °C / 1500.15 Torr / Inert atmosphere; Microwave irradiation
  • 55
  • [ 3133-78-6 ]
  • [ 1444018-29-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium <i>tert</i>-butylate / ethanol / 3 h / 20 °C / Inert atmosphere 2: copper(I) oxide; palladium diacetate; [2,2]bipyridinyl; 5,6-dichloro-2-(2-(dicyclohexylphosphino)phenyl)-1-methyl-1H-benzo[d]imidazole / 1-methyl-pyrrolidin-2-one; 1,3,5-trimethyl-benzene / 1 h / 170 °C / Inert atmosphere
  • 56
  • [ 445-27-2 ]
  • [ 3133-78-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 18 h / 0 - 20 °C / Inert atmosphere 2: water; lithium hydroxide / tetrahydrofuran; methanol / 4 h / 20 °C
  • 57
  • [ 3133-81-1 ]
  • [ 3133-78-6 ]
YieldReaction ConditionsOperation in experiment
0.742 g With water; lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 4h;
450 mg With lithium hydroxide monohydrate In methanol; water at 75℃; for 2h; 14 A mixture of 500 mg of methyl 3-methylbenzo[b]thiophene-2-carboxylate, 121 mg of lithium hydroxide monohydrate,4 ml of water, and 12 ml of methanol was stirred for 2 hours at 75°C. After being cooled to room temperature,the reaction mixture was concentrated under reduced pressure. Water was added to the residues, and the residue waswashed three times with tert-butyl methyl ether. Concentrated hydrochloric acid was added to the aqueous layer, andthen extraction was performed three times by using tert-butyl methyl ether. The collected organic layer was washed withsaturated saline, dried over magnesium sulfate, and then concentrated under reduced pressure, thereby obtaining 450mg of 3-methylbenzo[b]thiophene-2-carboxylic acid (hereinafter, described as a "compound 24 of the present invention").1H-NMR (CDCl3) δ: 7.88 (m, 2H), 7.49 (m, 2H), 2.82 (s, 3H).
  • 58
  • [ 3133-78-6 ]
  • [ 75-05-8 ]
  • 2-acetyl-1H-benzo[4,5]thieno[2,3-c]pyrrol-3(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With iron(III)-acetylacetonate; copper(II) nitrate; Selectfluor at 100℃; for 12h; Schlenk technique; Inert atmosphere;
  • 59
  • [ 3133-78-6 ]
  • 2-iodo-3-methylbenzo[b]thiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With copper(l) iodide; oxygen In dimethyl sulfoxide at 160℃; for 30h; Schlenk technique; Sealed tube;
90% With potassium phosphate; iodine In acetonitrile at 100℃; for 6h; Glovebox; Inert atmosphere; chemoselective reaction;
61% With N-iodo-succinimide; palladium diacetate In N,N-dimethyl-formamide at 80℃; for 12h; Inert atmosphere; Sealed tube; 17 Example 17 3-methylbenzothiophene-2-carboxylic acid (38.4 mg, 0.2 mmol), NIS (47.3 mg, 0.21 mmol), palladium acetate(0.9 mg, 0.002 mmol), and a stirrer were placed in the reaction tube. After replacing the inert gas, 1 ml of solvent DMF was added, Sealed reaction tube. The reaction tube was placed in an oil bath reaction reactor at 80 ° C and stirred for 12 hours. After cooling to room temperature, use 2 mol / L Sodium hydroxide solution to adjust pH = 10. The reaction tube was diluted with 5 ml of water and extracted with ethyl acetate. Combined extract, And dried over anhydrous sodium sulfate. The filtrate was concentrated under reduced pressure and then extracted with ethyl acetate: petroleum ether = 0 to 1: 30 (volume ratio) The eluate was subjected to column chromatography on the crude product to give pure 3-methyl-2-iodobenzothiophene (33.4 mg, 61%).
33% With 2.9-dimethyl-1,10-phenanthroline; oxygen; copper (I) acetate; silver sulfate; sodium iodide In dimethyl sulfoxide at 160℃; for 24h; Schlenk technique; 40 Example 40. Synthesis of 3-methyl-2-iodo-benzothiophene. Silak reaction tube equipped with a magnetic stirrer was charged with 6.2 mg of silver sulfate,21.8 mg of copper acetate, 12.5 mg of 2,9-dimethyl-1,10-o-phenanthroline,38.4 mg of 3-methyl-2-benzothiophenecarboxylic acid, and 45 mg of sodium iodide4 mL of dimethyl sulfoxide.The reaction was heated at 160 ° C for 24 hours in the presence of oxygen.After the reaction was completed, distilled water was added to quench the reaction,Extraction with ethyl acetate 3 times, each time 10mL,The combined organic phases are concentrated,18.1 mg of 3-methyl-2-iodo-benzothiophene was obtained in a yield of 33%.
Stage #1: 3-methylbenzo[b]thiophene-2-carboxylic acid With potassium phosphate; iodine In acetonitrile at 100℃; for 16h; Inert atmosphere; Stage #2: With triethylamine In acetonitrile at 120℃; for 5h; Inert atmosphere;

  • 60
  • [ 3133-78-6 ]
  • [ 5381-23-7 ]
YieldReaction ConditionsOperation in experiment
90% With potassium phosphate; tetrabuthylammonium tribromide In acetonitrile at 100℃;
79% With copper(l) iodide; oxygen; copper(I) bromide In dimethyl sulfoxide at 160℃; for 30h; Schlenk technique; Sealed tube;
22% With 2.9-dimethyl-1,10-phenanthroline; oxygen; copper (I) acetate; silver sulfate; sodium iodide In dimethyl sulfoxide at 160℃; for 24h; Schlenk technique; 41 Example 41. Synthesis of 3-methyl-2-bromo-benzothiophene. Silak reaction tube equipped with a magnetic stirrer was charged with 6.2 mg of silver sulfate,36.3 mg of copper acetate, 12.5 mg of 2,9-dimethyl-1,10-o-phenanthroline,38.4 mg of 3-methyl-2-benzothiophenecarboxylic acid,30.9 mg of sodium bromide and 4 mL of dimethylsulfoxide.The reaction was heated at 160 ° C for 24 hours in the presence of oxygen.After the reaction was completed, distilled water was added to quench the reaction,Extraction with ethyl acetate 3 times, each time 10mL,The combined organic phases are concentrated,10.0 mg of 3-methyl-2-bromo-benzothiophene was obtained in a yield of 22%.
  • 61
  • [ 3133-78-6 ]
  • [ 50288-76-1 ]
YieldReaction ConditionsOperation in experiment
76% With copper(l) iodide; oxygen; copper(l) chloride In dimethyl sulfoxide at 160℃; for 30h; Schlenk technique; Sealed tube;
33% With 2.9-dimethyl-1,10-phenanthroline; oxygen; copper (I) acetate; silver sulfate; sodium chloride In dimethyl sulfoxide at 160℃; for 24h; Schlenk technique; 42 Example 42. Synthesis of 3-methyl-2-chloro-benzothiophene. In a Schlak reaction tube equipped with a magnetic stirrer, 6.2 mg of silver sulfate was added36.3 mg of copper acetate, 12.5 mg of 2,9-dimethyl-1,10-o-phenanthroline,38.4 mg of 3-methyl-2-benzothiophenecarboxylic acid, and 17.5 mg of sodium chloride4 mL of dimethyl sulfoxide.The reaction was heated at 160 ° C for 24 hours in the presence of oxygen.After the reaction was completed, distilled water was added to quench the reaction,Extraction with ethyl acetate 3 times, each time 10mL,The combined organic phases are concentrated,12.1 mg of 3-methyl-2-chloro-benzothiophene was obtained in a yield of 33%.
  • 62
  • [ 3133-78-6 ]
  • [ 90-41-5 ]
  • N-(biphenyl-2-one)-3-hydroxymethylbenzo[b]thiophene-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20 - 40℃; for 26h; 233.1 Preparation of N-(biphenyl-2-yl)-3-methylbenzo[b]thiophene-2-carboxamide 3-methyl-benzo [b] thiophene-2-carboxylic acid (150 mg, 0.780 mmol), 2-amino-biphenyl (169 mg, 1.00 mmol), 1-ethyl-3- (3-dimethylaminopropyl) than carboxylic this hydrochloride (EDCI.HCl, 250 mg, 1.30 mmol) and hydroxybenzotriazole hydrate (HOBt.H2O, 180 mg, 1.33 mmol) and dichloromethane (10 mL) to dissolve and, at room temperature, stirred for 14 sigan dongan which it was then stirred for 12 hours at 40 . When the thin film croissant maeto Photography (TLC) check when a new spot is generated, and then concentrated under reduced pressure the reaction mixture. Column The concentrated reaction mixture was purified by chromatography (silica gel, ethyl acetate / n- hexane = l / 3 to 1/2) to obtain the compound (150 mg, 56%) as a white solid.
Stage #1: 3-methylbenzo[b]thiophene-2-carboxylic acid; 2-phenylaniline With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20 - 40℃; for 26h; Stage #2: With triethylamine In N,N-dimethyl-formamide at 120℃; for 0.25h; Microwave irradiation; 233 step 1: 3-methyl-benzo[b]thiophene-2-carboxylic acid ( 150 mg , 0.780 mmol ) , the 2-amino-biphenyl ( 169 mg , 1.00 mmol ) , 1-ethyl-3-(3-dimethylamino-propyl)-carbodiimide hydrochloride (EDCI.HCl , 250 mg , 1.30 mmol ) and hydroxybenzotriazole hydrate(HOBt.H2O , 180 mg , was dissolved while stirring 1.33 mmol) in dichloromethane ( 10 mL ) , 14 hours at room temperature ,At 40°C was stirred for 12 hours. When a thin layer chromatography maeto Croix (TLC) check when a new spot is created, the reaction mixture It was concentrated under reduced pressure . Column The concentrated reaction mixture was purified by chromatography (silica gel , ethyl acetate / n- hexane = 1 / 3 to 1 /2) to obtain the compound ( 150 mg , 56 % ) as a white solid The compound prepared in Step 1 ( 150 mg , 0.437 mmol ) , 2-amino-biphenyl ( 150 mg , 1.00 mmol ) and triethyl amine ( 100 mg , 0.99 mmol ) to dimethylformamide (3 mL) at 120°C in the electromagnetic wave ( microwave ) was dissolved in the reactor It was stirred for 15 minutes . When confirmation thin layer chromatography (TLC), when a new spot is generated , the reaction mixture was concentrated under reduced pressureIt was . Purification of the concentrated reaction mixture was purified by column chromatography (silica gel, ethyl acetate / n- hexane = l / 3 to 1/2)The desired compound ( 30 mg , 11 % ) as a white solid
  • 63
  • [ 6314-28-9 ]
  • [ 75-24-1 ]
  • [ 3133-78-6 ]
YieldReaction ConditionsOperation in experiment
55% Stage #1: benzo[b]thiophene-2-carboxylic acid; trimethylaluminum With iron(III)-acetylacetonate; 4-(bis(2-(diphenylphosphanyl)phenyl)phosphanyl)-N,N-dimethylaniline In tetrahydrofuran; 1,2-dimethoxyethane; toluene at 20℃; Inert atmosphere; Schlenk technique; Stage #2: With 2,3-dichlorobutane In tetrahydrofuran; 1,2-dimethoxyethane; toluene at 70℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube;
  • 64
  • [ 3133-78-6 ]
  • cis-2,6-dimethylmorpholine [ No CAS ]
  • (2,6-dimethylmorpholino)(3-methylbenzo[b]thiophen-2-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% Stage #1: 3-methylbenzo[b]thiophene-2-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere; Stage #2: cis-2,6-dimethylmorpholine With triethylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;
  • 65
  • [ 3133-78-6 ]
  • [ 115269-99-3 ]
  • [ 1436419-38-3 ]
YieldReaction ConditionsOperation in experiment
55% With palladium(II) trifluoroacetate; silver carbonate In tetrahydrofuran; dimethyl sulfoxide at 100℃; for 8h; Inert atmosphere; stereoselective reaction; 4.2. General procedure for the decarboxylative arylation of olefins with aryl carboxylic acids General procedure: To an oven-dried pressure tube were sequentially added aryl carboxylic acid 1 (0.2 mmol), olefin 2 (0.24 mmol), Pd(TFA)2 (3.33 mg, 5.0 mol%), Ag2CO3 (55.2 mg, 0.2 mmol), THF (2.0 mL) and DMSO (0.10 mL) under nitrogen at room temperature. After degassing three times, the reaction mixture was heated at 100 °C for 8 h, and then was cooled to room temperature. Water (20.0 mL)was added, and the mixture was extracted with ethyl acetate (3 5.0 mL). The combined organic layer was washed with brine, dried over anhydrious Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate) to give the pure target product.
  • 66
  • [ 3133-78-6 ]
  • [ 5428-09-1 ]
  • (E)-2-(3-(3-methylbenzo[b]thiophen-2-yl)allyl)isoindoline-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With palladium(II) trifluoroacetate; silver carbonate In tetrahydrofuran; dimethyl sulfoxide at 100℃; for 8h; Inert atmosphere; stereoselective reaction; 4.2. General procedure for the decarboxylative arylation of olefins with aryl carboxylic acids General procedure: To an oven-dried pressure tube were sequentially added aryl carboxylic acid 1 (0.2 mmol), olefin 2 (0.24 mmol), Pd(TFA)2 (3.33 mg, 5.0 mol%), Ag2CO3 (55.2 mg, 0.2 mmol), THF (2.0 mL) and DMSO (0.10 mL) under nitrogen at room temperature. After degassing three times, the reaction mixture was heated at 100 °C for 8 h, and then was cooled to room temperature. Water (20.0 mL)was added, and the mixture was extracted with ethyl acetate (3 5.0 mL). The combined organic layer was washed with brine, dried over anhydrious Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate) to give the pure target product.
  • 67
  • [ 3133-78-6 ]
  • 1-(4-methoxyphenyl)-2-(quinolin-8-yl)-1H-benzo[4,5]thieno[2,3-c]pyrrol-3(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: thionyl chloride / 15 h / 80 °C / Inert atmosphere 2: triethylamine / dichloromethane / 12.17 h / 20 °C / Reflux; Inert atmosphere 3: palladium diacetate; silver(I) acetate / toluene / 48 h / 110 °C / Inert atmosphere
  • 68
  • [ 3133-78-6 ]
  • 1-(4-chlorophenyl)-2-(quinolin-8-yl)-1H-benzo[4,5]thieno[2,3-c]pyrrol-3(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: thionyl chloride / 15 h / 80 °C / Inert atmosphere 2: triethylamine / dichloromethane / 12.17 h / 20 °C / Reflux; Inert atmosphere 3: palladium diacetate; silver(I) acetate / toluene / 48 h / 110 °C / Inert atmosphere
  • 69
  • [ 3133-78-6 ]
  • 1-(3,5-dimethylphenyl)-2-(quinolin-8-yl)-1H-benzo[4,5]thieno-[2,3-c]pyrrol-3(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: thionyl chloride / 15 h / 80 °C / Inert atmosphere 2: triethylamine / dichloromethane / 12.17 h / 20 °C / Reflux; Inert atmosphere 3: palladium diacetate; silver(I) acetate / toluene / 48 h / 110 °C / Inert atmosphere
  • 70
  • [ 3133-78-6 ]
  • 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-(quinolin-8-yl)-1Hbenzo[4,5]thieno[2,3-c]pyrrol-3(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: thionyl chloride / 15 h / 80 °C / Inert atmosphere 2: triethylamine / dichloromethane / 12.17 h / 20 °C / Reflux; Inert atmosphere 3: palladium diacetate; silver(I) acetate / toluene / 70 h / 110 °C / Inert atmosphere
  • 71
  • [ 3133-78-6 ]
  • [ 7101-31-7 ]
  • 3-methyl-2-(methylselanyl)benzo[b]thiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With 1,10-Phenanthroline; oxygen; copper diacetate; potassium carbonate In toluene at 140℃; for 24h; 4 Example 4Synthesis of 3 - methyl - 2 - methyl - selenobenzothiazole At room temperature3-methylbenzothiazole-2-carboxylic acid(0.4 mmol, 1 equiv), Cu (OAc) 2 (0.04 mmol), 1,10-o-phenanthroline (0.04 mmol)Potassium carbonate (1.2 mmol, 3 equiv) and 2 mL of toluene were added to the reaction tube,Then filled with oxygen, and replaced three times, in the oxygen reaction environment,Then add dimethyldiselenide (0.8 mmol, 2 equiv)And the mixture was stirred at a reaction temperature of 140 ° C for 24 h.After the reaction was monitored by thin layer chromatography, the reaction mixture was cooled,Then added to ethyl acetate to filter, then the solvent was removed,The product was isolated by column chromatography (eluent: petroleum ether: ether = 98: 2)The product was a yellow liquid in 90% yield and 87 mg of product.
77% With 1,10-Phenanthroline; oxygen; copper diacetate; potassium carbonate In toluene at 150℃; for 24h; Schlenk technique; Sealed tube;
  • 72
  • [ 95-16-9 ]
  • [ 3133-78-6 ]
  • 2-(3-methylbenzo[b]thiophen-2-yl)benzo[d]thiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With N,N′-bis(2,6-diisopropylphenyl)imidazol-2-ylidene hydrochloride; silver carbonate; cobalt(II) bromide at 160℃; for 24h; Sealed tube;
  • 73
  • [ 2786-51-8 ]
  • [ 3133-78-6 ]
  • 5-chloro-2-(3-methylbenzo[b]thiophen-2-yl)benzo[d]thiazole [ No CAS ]
  • 74
  • [ 2942-13-4 ]
  • [ 3133-78-6 ]
  • 6-methoxy-2-(3-methylbenzo[b]thiophen-2-yl)benzo[d]thiazole [ No CAS ]
  • 75
  • [ 273-53-0 ]
  • [ 3133-78-6 ]
  • 2-(3-methylbenzo[b]thiophen-2-yl)benzo[d]oxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With N,N′-bis(2,6-diisopropylphenyl)imidazol-2-ylidene hydrochloride; silver carbonate; cobalt(II) bromide at 160℃; for 24h; Sealed tube;
  • 76
  • [ 1006-68-4 ]
  • [ 3133-78-6 ]
  • 2-(3-methylbenzo[b]thiophen-2-yl)-5-phenyloxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
37% With N,N′-bis(2,6-diisopropylphenyl)imidazol-2-ylidene hydrochloride; silver carbonate; cobalt(II) bromide at 160℃; for 24h; Sealed tube;
  • 77
  • [ 3133-78-6 ]
  • [ 38061-18-6 ]
  • methyl 2-(3-methylbenzo[b]thiophen-2-yl)-5-phenyloxazole-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% With N,N′-bis(2,6-diisopropylphenyl)imidazol-2-ylidene hydrochloride; silver carbonate; cobalt(II) bromide at 160℃; for 24h; Sealed tube;
  • 78
  • benzoxazole-D<SUB>2</SUB> [ No CAS ]
  • [ 3133-78-6 ]
  • 2-(3-methylbenzo[b]thiophen-2-yl)benzo[d]oxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
16 %Spectr. With N,N′-bis(2,6-diisopropylphenyl)imidazol-2-ylidene hydrochloride; silver carbonate; cobalt(II) bromide at 160℃; for 1h; Sealed tube;
  • 79
  • [ 3133-78-6 ]
  • [ 20541-49-5 ]
  • 2-(4-chlorophenylselanyl)-3-methylbenzo[b]thiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With 1,10-Phenanthroline; oxygen; copper diacetate; potassium carbonate In toluene at 20 - 150℃; for 24h; 6 Example 6Synthesis of 2-(4-chlorophenylselenyl)-3-methylbenzothiophene At room temperature, 3-methyl-benzothiophene-2-carboxylic acid (0.4 mmol, 1 equiv), bis (4-chlorophenyl) diselenide (0.8mmol, 2equiv), Cu (OAc) 2 (0.06mmol ), 1,10-phenanthroline (0.06 mmol), potassium carbonate (1.2mmol, 3equiv) and 2mL of toluene was added to the reaction tube, then filled with oxygen, and substituted three times, the reaction in an oxygen environment, 150 reaction Stir for 24 h at the temperature. By the end of the reaction was monitored by thin layer chromatography, the reaction mixture was cooled, filtered and then ethyl acetate was added, and then spin off the solvent, the product obtained was isolated by column chromatography (eluent: petroleum ether: diethyl ether = 98), the product is Yellow liquid, yield 80%, product weight 108 mg.
71% With 1,10-Phenanthroline; oxygen; copper diacetate; potassium carbonate In toluene at 150℃; for 24h; Schlenk technique; Sealed tube;
  • 80
  • [ 3133-78-6 ]
  • [ 84019-98-7 ]
  • 4-(3-methylbenzo[b]thiophen-2-ylselanyl)benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With 1,10-Phenanthroline; oxygen; copper diacetate; potassium carbonate In toluene at 20 - 150℃; for 24h; 5 Example 5Synthesis of 4-(3-methylbenzothiophene-2-selenyl)benzonitrile At room temperature, 3-methyl-benzothiophene-2-carboxylic acid (0.4 mmol, 1 equiv), bis (4-cyanophenyl) diselenide (0.8mmol, 2equiv), Cu (OAc) 2 (0.06mmol ), 1,10-Phenanthroline (0.06 mmol), Potassium carbonate (1.2 mmol, 3 equiv), and 2 mL of toluene were added to the reaction tube, which was then filled with oxygen and replaced three times, under an oxygen reaction environment, at 150°C. Stir for 24 h at the temperature. By the end of the reaction was monitored by thin layer chromatography, the reaction mixture was cooled, filtered and then ethyl acetate was added, and then spin off the solvent, the product obtained was isolated by column chromatography (eluent: petroleum ether: diethyl ether = 98), the product is Yellow liquid, yield 83%, product weight 109 mg.
65% With 1,10-Phenanthroline; oxygen; copper diacetate; potassium carbonate In toluene at 150℃; for 24h; Schlenk technique; Sealed tube;
  • 81
  • [ 3133-78-6 ]
  • [ 1666-13-3 ]
  • 3-methyl-2-(phenylselanyl)benzo[b]thiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With 1,10-Phenanthroline; oxygen; copper diacetate; potassium carbonate In toluene at 150℃; for 24h; Schlenk technique; Sealed tube;
76% With 1,10-Phenanthroline; oxygen; copper diacetate; potassium carbonate In toluene at 20 - 150℃; for 24h; 2 Example 2Synthesis of 3-Methyl-2-phenylselenobenzothiophene At room temperature, 3-methyl - benzothiophene-2-carboxylic acid (0.4 mmol, 1 equiv), diphenyl diselenide (0.8mmol, 2equiv), Cu (OAc) 2 (0.06mmol), 1, 10- phenanthroline (0.06 mmol), potassium carbonate (1.2mmol, 3equiv) and 2mL of toluene was added to the reaction tube, then filled with oxygen, and substituted three times, the reaction in an oxygen environment at a reaction temperature 150 stirred 24h . By the end of the reaction was monitored by thin layer chromatography, the reaction mixture was cooled, filtered and then ethyl acetate was added, and then spin off the solvent, the product obtained was isolated by column chromatography (eluent: petroleum ether: diethyl ether = 98), the product is yellow liquid, yield 76%, by weight of the product 92mg.
  • 82
  • [ 3133-78-6 ]
  • 2-iodo-3-methylbenzofuran [ No CAS ]
YieldReaction ConditionsOperation in experiment
17% With 2.9-dimethyl-1,10-phenanthroline; oxygen; copper (I) acetate; silver sulfate; sodium chloride In dimethyl sulfoxide at 160℃; for 24h; Schlenk technique; 43 Example 43. Synthesis of 3-methyl-2-iodo-benzofuran. Equipped with a magnetic stirrerShylockThe reaction tube was added 6.2 mg silver sulfate,21.8 mg of copper acetate, 12.5 mg of 2,9-dimethyl-1,10-o-phenanthroline,35.2 mg of 3-methyl-2-benzofurancarboxylic acid, and 45 mg of sodium iodide4 mL of dimethyl sulfoxide.The reaction was heated at 160 ° C for 24 hours in the presence of oxygen.After the reaction was completed, distilled water was added to quench the reaction,Extraction with ethyl acetate 3 times, each time 10mL,The combined organic phases are concentrated,There was obtained 8.8 mg of 3-methyl-2-iodo-benzofuran in a yield of 17%.
  • 83
  • [ 3133-78-6 ]
  • 4-chloro-2-(3-methylbenzo[b]thiophen-2-yl)quinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 20 °C 1.2: 8 h / 90 °C 2.1: trichlorophosphate / N,N-dimethyl-formamide / 1 h / 120 °C / Cooling with ice
Multi-step reaction with 2 steps 1.1: N,N-dimethyl-formamide; phosgene / dichloromethane / 20 °C 1.2: 8 h / 100 °C 2.1: trichlorophosphate / N,N-dimethyl-formamide / 6 h / 80 °C
  • 84
  • [ 3133-78-6 ]
  • [ 28144-70-9 ]
  • 2-(3-methylbenzo[b]thiophen-2-yl)quinazolin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% Stage #1: 3-methylbenzo[b]thiophene-2-carboxylic acid With phosgene; N,N-dimethyl-formamide In dichloromethane at 20℃; Stage #2: anthranilic acid amide With potassium <i>tert</i>-butylate In <i>tert</i>-butyl alcohol at 100℃; for 8h; General method B for the preparation of the compounds m-n, s. General procedure: Toa stirred suspension of carboxylic acid k, l or q in dry dichloromethanewas added acyl chloride (3 eq) and two drops of DMF, andthe mixture was stirred at room temperature for 2 h. Next, the acylchloridewas removed by using a rotary evaporator. The residuewasdissolved in tert-butanol, then anthranilamide (1 eq) and potassiumtert-butoxide (2 eq) were added, and it was heated at 100 Cfor 8 h. The solution was poured into ice-water, and the pH was adjusted to 7.0. The residue was filtered, washed with water, anddesiccated under vacuum to give the crude product, which wasthen purified by using column chromatography to give the desiredproduct.
5.3 g Stage #1: 3-methylbenzo[b]thiophene-2-carboxylic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h; Stage #2: anthranilic acid amide With potassium <i>tert</i>-butylate In ethanol; dichloromethane at 90℃; for 8h; 24 Example 24: BYSO8 3-methylbenzothiophene-2-carboxylic acid (8 g, 41.7 mmol) was dissolved in a round-bottomed flask containing 30 mL of water-free dichloromethane.Oxalyl chloride (10.5 mL, 125 mmol) and 2 drops of N,N-dimethylformamide as catalysts were added at room temperature.After 2 hours of reaction, the solvent was derotated and dissolved with ethanol.7.2g of o-aminobenzamide was added and it turned yellow and turbid immediately.Then add 30g of potassium tert-butoxide,The temperature was slowly raised to 90 °C for about 8 hours, and the reaction was stopped. After the reaction solution was cooled to room temperature, the filtrate was obtained by filtration.The filtrate was poured into ice water and a large amount of solids were precipitated by ultrasound.Adjust pH to about 8 with dilute hydrochloric acid,5.3 g white yellowish solid (intermediate BYS-1) was filtered.
  • 85
  • [ 3133-78-6 ]
  • [ 111-66-0 ]
  • 3-methyl-2-(oct-1-en-2-yl)benzo[b]thiophene [ No CAS ]
  • C17H22S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With palladium(II) trifluoroacetate; Bathocuproine; p-benzoquinone In dimethyl sulfoxide; N,N-dimethyl-formamide at 130℃; for 4h; Inert atmosphere; Schlenk technique; Sealed tube; Overall yield = 64 %; Overall yield = 41.3 mg; regioselective reaction;
  • 86
  • [ 3133-78-6 ]
  • [ 1746-13-0 ]
  • 3-methyl-2-(3-phenoxyprop-1-en-2-yl)benzo[b]thiophene [ No CAS ]
  • C18H16OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
With palladium(II) trifluoroacetate; Bathocuproine; p-benzoquinone In dimethyl sulfoxide; N,N-dimethyl-formamide at 130℃; for 4h; Inert atmosphere; Schlenk technique; Sealed tube; Overall yield = 71 %; Overall yield = 49.6 mg; regioselective reaction;
  • 87
  • [ 3133-78-6 ]
  • [ 75-09-2 ]
  • C21H16O4S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With potassium carbonate In dimethyl sulfoxide at 130℃; for 5h; General procedure for synthesis of Dichloromethyl Esters under metal-free conditions. General procedure: An oven-dried Schlenk tube equipped with a stir bar was charged with carboxylic acid (0.2 mmol) and K2CO3 (55.3 mg, 0.4 mmol, 2 equiv.). The tube was fitted with a rubber septum, DMSO (1 mL) and CH2Cl2 (1 mL) was added via syringe at air. With stirring, the reaction mixtures were heated at 130 °C for 5 h (unless otherwise specified), and then cooled down to room temperature. The resultant mixture was filtered through a short plug of silica gel and then concentrated in vacuo. The residue was then purified by flash chromatography on silica gel to provide the corresponding product. For the substrates 26, 31 were heated at 140 °C for 8 h under otherwise identical conditions.
  • 88
  • [ 3133-78-6 ]
  • [ 64-17-5 ]
  • [ 31310-22-2 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride at 0 - 85℃; i To a solution of 3-methylbenzo[b]thiophene-2-carboxylic acid (800 mg, 4.16 mmol) in EtOH (40 mL) at 0 °C was added SOCh (30 mL) and the mixture was heated at 85 °C overnight then concentrated under reduced pressure. The residue was purified by silica gel chromatography (Pet. Ether/EtOAc = 1 :0 to 30:1 ) to give the title product (754 mg, 82%) as a white solid. LCMS-C: rt2.62 min; m/z 221.0 [M+H]+.
  • 89
  • [ 3133-78-6 ]
  • N1,N1-dimethyl-N2-(2-(3-methylbenzo[b]thiophen-2-yl)quinazolin-4-yl)ethane-1,2-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N,N-dimethyl-formamide; phosgene / dichloromethane / 20 °C 1.2: 8 h / 100 °C 2.1: trichlorophosphate / N,N-dimethyl-formamide / 6 h / 80 °C 3.1: triethylamine / toluene / 2 h / 25 - 60 °C
  • 90
  • [ 3133-78-6 ]
  • N1,N1-dimethyl-N3-(2-(3-methylbenzo[b]thiophen-2-yl)quinazolin-4-yl)propane-1,3-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N,N-dimethyl-formamide; phosgene / dichloromethane / 20 °C 1.2: 8 h / 100 °C 2.1: trichlorophosphate / N,N-dimethyl-formamide / 6 h / 80 °C 3.1: triethylamine / toluene / 2 h / 25 - 60 °C
  • 91
  • [ 3133-78-6 ]
  • 2-(3-methylbenzo[b]thiophen-2-yl)-N-(2-(pyrrolidin-1-yl)ethyl)quinazolin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N,N-dimethyl-formamide; phosgene / dichloromethane / 20 °C 1.2: 8 h / 100 °C 2.1: trichlorophosphate / N,N-dimethyl-formamide / 6 h / 80 °C 3.1: triethylamine / toluene / 2 h / 25 - 60 °C
  • 92
  • [ 3133-78-6 ]
  • 2-(3-methylbenzo[b]thiophen-2-yl)-N-(3-(pyrrolidin-1-yl)propyl)quinazolin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N,N-dimethyl-formamide; phosgene / dichloromethane / 20 °C 1.2: 8 h / 100 °C 2.1: trichlorophosphate / N,N-dimethyl-formamide / 6 h / 80 °C 3.1: triethylamine / toluene / 2 h / 25 - 60 °C
  • 93
  • [ 3133-78-6 ]
  • 2-(3-methylbenzo[b]thiophen-2-yl)-N-(4-(pyrrolidin-1-yl)butyl)quinazolin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N,N-dimethyl-formamide; phosgene / dichloromethane / 20 °C 1.2: 8 h / 100 °C 2.1: trichlorophosphate / N,N-dimethyl-formamide / 6 h / 80 °C 3.1: triethylamine / toluene / 2 h / 25 - 60 °C
  • 94
  • [ 3133-78-6 ]
  • CH3O3SSe(1-)*Na(1+) [ No CAS ]
  • 3-methyl-2-(methylselanyl)benzo[b]thiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With copper(l) iodide; 1,10-Phenanthroline; oxygen; caesium carbonate; silver carbonate In N,N-dimethyl-formamide at 80 - 140℃; for 24h; 4 At room temperature, the selenium methyl boonte salt (0.8mmol, 4.0equiv),3-methylbenzo[B]thiophene-2-carboxylic acid (0.2mmol, 1.0equiv),Cuprous iodide (0.04mmol, 0.2equiv),1,10-phenanthroline (0.04mmol, 0.2equiv),Silver carbonate (0.4mmol, 2.0equiv),Cesium carbonate (0.4mmol, 2.0equiv)And 2mL N,N-dimethylformamide were added to the reaction tube,Then pump down-fill with oxygen, and replace three times,Stir at 80°C reaction temperature for 24h.The reaction mixture was cooled, then ethyl acetate was added for dilution,Extract with brine, separate the organic phase, dry with anhydrous sodium sulfate, filter to a chicken heart bottle, and then spin off the solvent.The product is separated by column chromatography (eluent: petroleum ether),The product is a yellow liquid, the yield is 65%, and the product weight is 31 mg.
  • 95
  • [ 3133-78-6 ]
  • [ 109-77-3 ]
  • [ 3216-49-7 ]
YieldReaction ConditionsOperation in experiment
33% With potassium phosphate; copper(l) iodide; oxygen In N,N-dimethyl-formamide at 170℃; for 20h; Schlenk technique; Green chemistry;
  • 96
  • [ 3133-78-6 ]
  • [ 13472-08-7 ]
  • [ 3216-49-7 ]
YieldReaction ConditionsOperation in experiment
65% With potassium phosphate; copper(l) iodide; oxygen In N,N-dimethyl-formamide at 160℃; for 20h; Schlenk technique; Green chemistry;
  • 97
  • [ 3133-78-6 ]
  • 2,2,2,-trichloroethoxycarbonyl azide [ No CAS ]
  • 2,2,2-trichloroethyl (3-methylbenzo[b]thiophen-2-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With dmap; copper diacetate In acetonitrile at 100℃; for 3h; Schlenk technique; Sealed tube; Inert atmosphere;
  • 98
  • [ 3133-78-6 ]
  • [ 4242-46-0 ]
  • 4-(3-methylbe nzo[b]thiophen-2-yl)-2,5-diphenyloxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With 6,6'-dimethyl-2,2'-bipyridine; heptafluorobutyric Acid; palladium diacetate at 130℃; for 24h; Schlenk technique;
  • 99
  • [ 3133-78-6 ]
  • 4-methyl-8-(3-methylbenzo[b]thiophen-2-yl)-2,6-dioxohexahydro[1,3,2]oxazaborolo[2,3-b][1,3,2]oxazaborol-4-ium 8-uide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: bis(1,5-cyclooctadiene)nickel (0); bis(dicyclohexylphosphino)methane / toluene / 24 h / 150 °C / Inert atmosphere; Schlenk technique; Sealed tube 2: toluene; N,N-dimethyl-formamide / 4 h / 90 °C / Inert atmosphere; Schlenk technique; Sealed tube
  • 100
  • [ 3133-78-6 ]
  • [ 13826-27-2 ]
  • C15H11BO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With bis(1,5-cyclooctadiene)nickel (0); bis(dicyclohexylphosphino)methane In toluene at 150℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube;
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