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[ CAS No. 162607-23-0 ]

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Chemical Structure| 162607-23-0
Chemical Structure| 162607-23-0
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CAS No. :162607-23-0 MDL No. :MFCD09837620
Formula : C6H9BO2S Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :156.01 g/mol Pubchem ID :-
Synonyms :

Safety of [ 162607-23-0 ]

Signal Word:Warning Class:
Precautionary Statements:P305+P351+P338 UN#:
Hazard Statements:H319 Packing Group:
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Application In Synthesis of [ 162607-23-0 ]

  • Downstream synthetic route of [ 162607-23-0 ]

[ 162607-23-0 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 56290-06-3 ]
  • [ 162607-23-0 ]
  • [ 792934-46-4 ]
YieldReaction ConditionsOperation in experiment
44% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran Heating;
44% With sodium carbonate In tetrahydrofuran Heating;
With sodium carbonate In tetrahydrofuran; water 1; 1 Example 1; FIG. 1 The ligand (LI) is synthesized by the Suzuki cross-coupling reactions of 2.5 equivalents of 2, 5-dimethyl-3-thienylboronic acid and 5, 6-dibromo-1, 10- phenanthroline in the presence of the palladium catalyst, Pd (PPH3) 4, and sodium carbonate in a heterogeneous mixture of water AND THE ACCORDING to the synthetic route depicted in Fig. 1. Excitation of (L1) with 313 nm light resulted in the formation of the close form, corresponding to the photocyclization product. The overlaid electronic absorption spectra of the open and close forms of (LI) in benzene solution are shown in Fig. 2.
  • 2
  • [ 31819-37-1 ]
  • [ 162607-23-0 ]
YieldReaction ConditionsOperation in experiment
In a Schlenk flask under argon <strong>[31819-37-1]3-bromo-2,5-dimethylthiophene</strong> (1 g,5.23 mmol) was mixed with dry THF (30 mL) and degassed. Thesolution was cooled to -78 C, n-BuLi (3 mL, 7.33 mmol, 2.5 M inhexane) was added dropwise and the mixture was stirred for 30 min at-78 C.Tributyl borate (1.93 g, 8.37 mmol) was added and the reaction mixture was stirred for 1 h at-78 C. The solution was heated to rt, aq Na2CO3 solution (20%, 5 mL), Pd(dppf)Cl2 (214mg, 0.262 mmol) and 1,2 dibromocyclopentene (1.42 g, 6.28 mmol) were added. The mixturewas heated to 75 C and stirred under reflux overnight. The reaction mixture was extractedwith ethyl acetate three times. The combined organic phases were washed with water andbrine, dried over MgSO4, filtered and the solvent was removed under reduced pressure.Purification by flash column chromatography (pure cyclohexane) afforded a yellowish oilwith a yield of 90%.
  • 3
  • [ 18392-81-9 ]
  • [ 162607-23-0 ]
  • [ 1216277-34-7 ]
  • 4
  • [ 1258399-08-4 ]
  • [ 162607-23-0 ]
  • [ 1258401-86-3 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate In water; toluene at 100℃; Inert atmosphere; 3 Example 3[ (3S)-6-{ [ (3S)-7-(2,5-dimethylthiophen-3-yl)-2,3-dihydro-l- benzofuran-3-yl] amino} -2, 3-dihydro-l-benzofuran-3-yl] acetic acid; [0664] [ 0665 ]To a solution of methyl [ (3S) -6-{ [ (3S) -7-bromo-2, 3- dihydro-l-benzofuran-3-yl] (trifluoroacetyl) amino} -2, 3-dihydro- l-benzofuran-3-yl] acetate (200 mg, 0.400 mmol) , (2,5- dimethylthiophen-3-yl) boronic acid (74.8 mg, 0.480 mmol) and 2 M aqueous sodium carbonate solution (0.600 mL, 1.20 mmol) in toluene (2 mL) were added tris (dibenzylideneacetone) dipalladium (0) (14.7 mg, 0.016 mmol) and dicyclohexyl (2' , 6' -dimethoxybiphenyl-2-yl) phosphane(26.3 mg, 0.064 mmol) under an argon atmosphere, and the mixture was stirred at 100°C overnight. The reaction mixture was cooled to room temperature, filtered through celite, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 95:5 - 70:30) to give a colorless oil (230 mg) . To a mixed solution of the obtained oil (230 mg) in tetrahydrofuran (2.7 mL) and methanol (1.35 mL) was added 1 M aqueous sodium hydroxide solution (1.30 mL) , and the mixture was stirred at 5O0C for 1 hr. The reaction mixture was neutralized with 1 M hydrochloric acid, diluted with distilled water, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound(114 mg, yield 61%) as a white solid.1H NMR (300 MHz, CDCl3) δ 2.37 (3H, br s) , 2.44 (3H, br s) , 2.53-2.72 (IH, m) , 2.73-2.91 (IH, m) , 3.79 (IH, br s) , 4.20-4.35 (IH, m) , 4.35-4.50 (IH, m) , 4.73 (2H, d, J = 8.3 Hz), 5.20 (IH, br s) , 6.14 (2H, br s) , 6.74 (IH, br s) , 6.86-7.11(2H, m), 7.13-7.41 (2H, m) . MS m/z 422 (M + H)+. [0666]
  • 5
  • [ 1258397-21-5 ]
  • [ 162607-23-0 ]
  • [ 1258397-38-4 ]
YieldReaction ConditionsOperation in experiment
86% With sodium carbonate In water; toluene at 100℃; Inert atmosphere; 122 Example 122 methyl [ (3S)-6-{ [3- (2, 5-dimethylthiophen-3-yl) -2- methylbenzyl] amino} -2, 3-dihydro-l-benzofuran-3-yl] acetate; [1026][1027]To a solution of methyl { (3S) -6- [ (3-bromo-2- methylbenzyl) amino] -2, 3-dihydro-l-benzofuran-3-yl} acetate (150 mg, 0.384 mmol), (2, 5-dimethylthiophen-3-yl) boronic acid (120 mg, 0.769 mmol) and 2 M aqueous sodium carbonate solution (0.576 mL, 1.15 mmol) in toluene (2 mL) were added tris (dibenzylideneacetone)dipalladium (0) (10.5 mg. 0.012 mmol) and dicyclohexyl (2' , 6' -dimethoxybiphenyl-2-yl) phosphane(18.9 mg, 0.046 mmol) under an argon atmosphere, and the mixture was stirred at 100°C overnight. The reaction mixture was cooled to room temperature, filtered through celite, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 95:5 - 67:33) to give the title compound (140 mg, yield 86%) as a yellow oil.1H NMR (300 MHz, CDCl3) δ 2.15 (3H, s) , 2.18 (3H, s) , 2.45 (3H, s), 2.54 (IH, dd, J = 16.3, 9.1 Hz), 2.74 (IH, dd, J = 16.3, 5.7 Hz), 3.71 (3H, s) , 3.73-3.83 (IH, m) , 3.91 (IH, br s) , 4.23 (IH, dd, J = 9.1, 6.1 Hz), 4.27 (2H, s) , 4.72 (IH, t, J = 8.9 Hz), 6.13-6.22 (2H, m) , 6.50 (IH, s) , 6.95 (IH, d, J = 8.0 Hz), 7.05-7.12 (IH, m) , 7.17 (IH, t, J = 7.6 Hz), 7.23-7.34(IH, m) . MS m/z 422 (M + H)+.
  • 6
  • [ 859299-66-4 ]
  • [ 123-31-9 ]
  • [ 162607-23-0 ]
  • [ 1263049-56-4 ]
  • [ 1263049-59-7 ]
  • [ 1263049-54-2 ]
  • [ 147699-65-8 ]
  • 7
  • [ 859299-66-4 ]
  • [ 162607-23-0 ]
  • [ 1263049-57-5 ]
  • [ 1263049-51-9 ]
  • 8
  • [ 49764-63-8 ]
  • [ 162607-23-0 ]
  • [ 1429780-58-4 ]
  • 9
  • [ 31819-37-1 ]
  • [ 688-74-4 ]
  • [ 162607-23-0 ]
YieldReaction ConditionsOperation in experiment
73% 3-Bromo-2,5-dimethylthiophene (2 g, 1 equiv., 10.47 mmol)was dissolved in 40 mL anhydrous tetrahydrofuran (THF). n-Butyllithium (2.5 M in hexane, 6.28 mL, 1.1 equiv.,11.51 mmol) was slowly added at -78 C, and the reactionsolution was stirred at the same temperature for 15 min. Asolution of tri-n-butyl borate (3.09 mL, 1.1 equiv.,11.51 mmol) in THF (10 mL) was added over a period of10 min. The reaction solution was slowly heated to roomtemperature and stirred for 8 h. Then 9 mL 2 M HCl wasadded and the mixture was stirred for another 10 h. After thereaction was completed, the excess solvent was removed andNaOH solution was added to neutralize. The resulting mixturewas extracted with dichloromethane and water for threetimes before the combined organic phases were dried overMgSO4 and the solvent was removed to obtain a crudeproduct. The crude product was dissolved in 15 mL of dichloromethaneand washed three times with 2 M NaOH solution. The resulting aqueous phases were combined and10 mL concentrated hydrochloric acid (12 M) was addeddropwise to commence the precipitation of 4 in a 73% yield as a white powder (1.2 g). 1H NMR (400 MHz, CDCl3): δ7.07 (s, 1H), 2.82 (s, 3H), 2.46 (s, 3H).
  • 10
  • [ 7209-12-3 ]
  • [ 162607-23-0 ]
  • [ 1435464-41-7 ]
YieldReaction ConditionsOperation in experiment
90% With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In 1,4-dioxane; water monomer at 110℃; Inert atmosphere;
65% With tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate In tetrahydrofuran; water monomer Reflux; Darkness;
  • 11
  • [ 5788-58-9 ]
  • [ 162607-23-0 ]
  • 4,5-bis(2,5-dimethylthiophen-3-yl)pyridazin-3(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.075g With tris-(dibenzylideneacetone)dipalladium(0); tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 40 - 50℃; for 3h;Inert atmosphere; A mixture of <strong>[5788-58-9]4,5-dibromopyridazin-3(2H)-one</strong> (1) (0.20 g, 0.79 mmol), (2,5-dimethylthiophen-3-yl) boronic acid (4) (0.37 g, 2.36 mmol), potassium carbonate (1.08 g, 7.84 mmol), tetrakis(triphenylphosphine) palladium(0) (0.11 g, 0.095 mmol), and a catalytic amount of tris(dibenzylideneacetone) dipalladium(0) in THF (10 ml) and H2O (2 ml) was stirred for 1 h at 40-50 C, and then this mixture was refluxed for 2 h. The progress of reaction was monitored by TLC. The reaction mixture was quenched by aqueous solutions of 10% NaHCO3 and extracted with ethyl acetate. The organic layer was washed with sat. aq. NaCl, dried with anhydrous Na2SO4, and the drying agent was filtered off. After removing the solvent in a rotary evaporator, the mixture was purified by column chromatography on silica gel using ethyl acetate/hexane as the eluent. Further purifications were required by preparative thin layer chromatography (PTLC) to obtain 1O as a white solid. Yield 0.075 g (30%) mp: 134-135 C. 1H NMR (400 MHz, CDCl3, ppm): delta 1.92 (3H, s, Me), 2.06 (3H, s, Me), 2.37 (3H, s, Me), 2.35 (3H, s, Me), 6.28 (1H, s, thienyl-H), 6.52 (1H, s, thienyl-H), 7.79 (1H, s, pyridazinone-H). Calculated for C16H16N2OS2: 316.44; ESI-317.0000 (M + H)+. FT-IR (ATR) ?/cm-1: 3288, 2929, 1732, 1638.
  • 12
  • [ 14305-08-9 ]
  • [ 162607-23-0 ]
  • 4,5-bis(2,5-dimethylthiophen-3-yl)-2-phenylpyridazin-3(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.095g With tris-(dibenzylideneacetone)dipalladium(0); tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 40 - 50℃; for 3h;Inert atmosphere; General procedure: A mixture of 4,5-dibromopyridazin-3(2H)-one (1) (0.20 g, 0.79 mmol), (2,5-dimethylthiophen-3-yl) boronic acid (4) (0.37 g, 2.36 mmol), potassium carbonate (1.08 g, 7.84 mmol), tetrakis(triphenylphosphine) palladium(0) (0.11 g, 0.095 mmol), and a catalytic amount of tris(dibenzylideneacetone) dipalladium(0) in THF (10 ml) and H2O (2 ml) was stirred for 1 h at 40-50 C, and then this mixture was refluxed for 2 h. The progress of reaction was monitored by TLC. The reaction mixture was quenched by aqueous solutions of 10% NaHCO3 and extracted with ethyl acetate. The organic layer was washed with sat. aq. NaCl, dried with anhydrous Na2SO4, and the drying agent was filtered off. After removing the solvent in a rotary evaporator, the mixture was purified by column chromatography on silica gel using ethyl acetate/hexane as the eluent. Further purifications were required by preparative thin layer chromatography (PTLC) to obtain 1O as a white solid. Yield 0.075 g (30%) mp: 134-135 C.
  • 13
  • [ 1617523-10-0 ]
  • [ 162607-23-0 ]
  • N-(2,6-difluoro-phenyl)-5-(2,5-dimethyl-thiophen-3-yl)-1-methyl-1H-pyrazole-3-carboxylic acid amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In tetrahydrofuran; water at 100℃; for 3h; Microwave irradiation; 17 W-(2,6-Difluoro-phenyl)-5-(2,5-dimethyl-thiophen-3-yl)-1 -methyl-1 H-pyrazole-3- carboxylic acid amide A mixture of 2,5-dimethylthiophen-3-ylboronic acid (100 mg, 641 pmol), BB-1 (203 mg, 641 pmol) and Pd(dppf)CI2-CH2CI2 (24 mg, 32 pmol) in THF (4 mL) and aqueous Na2C03 (2M, 0.9 mL) was heated in a microwave to 100°C for 3 h. Saturated NH4CI was added and the organic phase was separated. The volatiles were removed and the residue was purified by chromatography (Interchim cartridge50SiHP / 12 g, Cy/EtOAc) to yield example 17 ( 70 mg, 76%). LC-MS (Method 2): m/z: [M+Hf = 348.1 (MW calc. = 347.09), R, = 0.79 min. 1H-NMR (DMSO-d6): δ = 9.83 (s, 1 H), 7.41 -7.35 (m, 1 H), 7.20-7.15 (m, 2H), 6.85 (s, 1 H), 6.76 (s, 1 H), 3.82 (s, 3H), 2.43 (s, 3H), 2.33 (s, 3H) ppm.
  • 14
  • [ 154566-69-5 ]
  • [ 162607-23-0 ]
  • 15
  • [ 31819-37-1 ]
  • [ 5419-55-6 ]
  • [ 162607-23-0 ]
  • 16
  • [ 1309387-42-5 ]
  • [ 162607-23-0 ]
  • 5-(2,5-dimethylthiophen-3-yl)-2,9-di(undecan-6-yl)anthra[2,1,9-def:6,5,10-d’e’f’]diisoquinoline-1,3,8,10(2H,9H)-tetraone [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 20h; Schlenk technique; Inert atmosphere; Sealed tube; Reflux; 2.2.1. Synthesis of 5-(2,5-dimethylthiophen-3-yl)-2,9-di(undecan-6-yl)anthra[2,1,9-def:6,5,10-d’e’f’] diisoquinoline-1,3,8,10(2H,9H)-tetraone(PBI-MT 1) A Schlenk tube containing PBI-MT (0.50 g, 0.64 mmol), (2,5-dimethyl-3-thiophenyl) boronic acid (0.15 g, 0.96 mmol), and Pd(PPh3)4 (0.05 g, 0.04 mmol) was evacuated and backfilled with argon forthree times. After the addition of degassed K2CO3 (aq. 2 mL), ethanol (1ml) and toluene (5 mL), the tube was sealed under argon atmosphereand heated at refllux for 20 h. After being cooled to room temperature,the reaction mixture was diluted with dichloromethane, washed withwater, and dried over anhydrous Na2SO4. Upon removal of solvents invacuo, the residual was purified with column chromatography over silicagel eluted with petroleum ether/dichloromethane (2/1, v/v) in darkenvironment to afford PBI-MT 1 as a red solid (0.43 g, 83%). 1H NMR(400 MHz, CDCl3, ppm): 8.70-8.60 (m, 4H), 8.50 (d, J 4.2 Hz, 1H),8.35-8.26 (m, 1H), 8.12 (d, J 8.3 Hz, 1H), 6.62 (s, 1H), 5.22-5.13 (m,2H), 2.51 (s, 3H), 2.28-2.18 (m, 4H), 2.14 (s, 3H), 1.83 (dd, J 13.1,5.3 Hz, 4H), 1.26 (d, J 3.1 Hz, 24H), 0.86-0.80 (m, 12H). 13C NMR(101 MHz, CDCl3, ppm): 164.79, 163.67, 139.64, 138.45, 136.20,135.23, 134.76, 134.45, 133.07, 132.26, 131.36, 130.71, 129.18,128.58, 127.87, 127.78, 127.27, 125.27, 123.40, 122.65, 54.72, 32.32,31.76, 29.70, 26.62, 22.56, 15.44, 14.05, 13.71. MALDI TOF MS (HR):Calc’d for C52H60N2O4S, 808.4274; Found Mass (M), 808.4678 (m/z).
  • 17
  • [ 2592-73-6 ]
  • [ 162607-23-0 ]
  • 3,3’-(2,2-diphenylethene-1,1-diyl)bis(2,5-dimethylthiophene) [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 12h; Inert atmosphere; 2.2.4. Synthesis of 3,3’-(2,2-diphenylethene-1,1-diyl)bis(2,5-dimethylthiophene) (TAE-3) To a mixture of compound 1 (200 mg, 0.6 mmol), compound 2 (374mg, 2.4 mmol), Pd(PPh3)4 (69 mg, 0.06 mmol), and K2CO3 (1.38 g, 10mmol) in a nitrogen flushed two-necked flask, THF/H2O (50 mL, 4:1, v/v) was added. The reaction was allowed to stir at 80°C for 12 h. After completion, the reaction was quenched with water and extracted with CH2C12 for three times. The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuum. The crude product was purified by flash column chromatography with PE as eluent to give a white solid (156 mg, 65% yield). 1H NMR (400 MHz, CDCl3) δ 7.14-7.12 (m, 6H),7.04-7.02 (m, 4H), 6.23 (s, 2H), 2.28 (s, 6H), 1.86 (s, 6H). 13C NMR (101MHz, CDCl3) δ 143.61, 142.96, 138.98, 134.71, 132.83, 130.92, 130.32,128.04, 127.58, 126.52, 15.33, 13.91. HR-MS (ESI+): m/z calcd for[C26H25S2]: [M+H]+: 401.1398; found 401.1400.
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