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[ CAS No. 1135871-91-8 ] {[proInfo.proName]}

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Chemical Structure| 1135871-91-8
Chemical Structure| 1135871-91-8
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Product Details of [ 1135871-91-8 ]

CAS No. :1135871-91-8 MDL No. :MFCD27936771
Formula : C16H21BO3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :272.15 Pubchem ID :-
Synonyms :

Safety of [ 1135871-91-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1135871-91-8 ]

* 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 [ 1135871-91-8 ]

[ 1135871-91-8 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 32281-97-3 ]
  • [ 73183-34-3 ]
  • [ 1135871-91-8 ]
YieldReaction ConditionsOperation in experiment
84% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In toluene at 90℃; for 12h; Inert atmosphere;
67% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In methanol at 65℃; for 14h; Inert atmosphere;
66% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In methanol at 60℃; for 10h; Inert atmosphere;
66% With potassium acetate In methanol at 60℃; for 14h; 36.a ) Preparation of l-tetralone-7-boronic ester7-Bromo-tetralone (200mg, 0.89 mmol), bis(pinacolato)diboron (296mg, 1.16 mmol), Potassium acetate (192mg, 1.78 mmol) and [l,l'-bis(diphenylphosphino)ferrocene]- dichloropalladium (17mg, 0.023 mmol) were dissolved in 4 mL methanol and the solution was stirred at 6O0C for 14 hours. The reaction was allowed to cool, filtered over celite and concentrated to give a dark oil. The crude product was purified by flash chromatography on silica, using petroleum benzine and then 9:1 ratio of petroleum benzine and ethyl acetate as eluent to give the boronic ester (160mg, 66%). 1H NMR (d-chloroform) δ (ppm): 1.31 (s, 12H); 2.11 (m, 2H); 2.63 (t, 2H); 2.95 (t, 2H), 7.21 (s, IH), 7.85 (dd, IH), 8.47 (s, IH).
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 1h; Inert atmosphere; 4.1 Step 1 : Preparation of 7-(4,4,5.5-tetramethyl-1,3.2-dioxaborolan-2-yl)tetralin-1 -one To a solution of 7-bromotetralin-1 -one (4.00 g, 17.8 mmol, 1 .00 equiv.) in dioxane (89.0 mL) was added potassium acetate (3.52 g, 35.5 mmol, 2.00 equiv.) and bis(pinacolato)diboron (5.01 g, 19.5 mmol, 1 .10 equiv.). The solution was degassed with argon for 5 min, then PdCl2(dppf) (0.68 g, 0.89 mmol, 0.05 equiv.) was introduced, and the reddish suspension was stirred at 100°C for 1 hour. The reaction mixture was diluted with EtOAc and water, and extracted with EtOAc. The total combined organic layer was washed with water and brine, dried with Na2SO 4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (cyclohexane:EtOAc) to give 7-(4,4,5,5-tetramethyl-1 ,3,2- dioxaborolan-2-yl)tetralin-1 -one as a yellow gum. LC-MS (Method A), Rt = 1 .13 min, MS: (M+H) = 273 1H NMR (400 MHz, CDCl3) d ppm: 8.49-8.55 (m, 1 H), 7.90 (dd, 1 H), 7.28 (s, 1 H), 3.00 (t, 2H), 2.66-2.71 (m, 2H), 2.16 (quin, 2H), 1 .36 (s, 12H)

  • 2
  • [ 321601-48-3 ]
  • [ 1135871-91-8 ]
  • [ 1135872-28-4 ]
YieldReaction ConditionsOperation in experiment
31% With tetrabutylammomium bromide; caesium carbonate In 1,4-dioxane; water at 100℃; for 1.5h; Microwave irradiation; 68.a a) 3-Hydroxy-6-(8-Oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)-pyridine-2-carboxylic acid methyl esterA mixture of methyl 6-bromo-3-hydroxypicolinate (lOOmg, 0.43 mmol), 7-pinacloatoborane-tetralone (129mg, 0.47 mmol), PdCl2(PPh3)2 (7.5mg, 2.5 mol%), tetrabutylammonium bromide (14mg, 0.043 mmol), caesium fluoride (145mg, 0.95 mmol) in dioxane:H2O (2:1, mL) was heated at 1000C under microwave irradiation for 90 minutes. The reaction was cooled, diluted with ethyl acetate and poured onto water. The aqueous phase was extracted with ethyl acetate (2 x 3mL), the organic layer was dried (MgSO4) and concentrated in vacuo. The residue was triturated with diethyl ether and the solid was filtered to afford an off-white solid (40mg, 31%). 1H NMR (d6-DMSO) δ: 10.55 (IH, bs), 8.42 (IH, d), 8.13 (IH, dd), 8.07 (IH, dd), 7.48 (IH, d), 7.43 (IH, d), 3.90 (3H, s), 2.96 (2H, t), 2.61 (2H, t), 2.07-2.01 (2H, m).
  • 3
  • [ 1135871-91-8 ]
  • [ 460081-18-9 ]
  • [ 1135872-20-6 ]
YieldReaction ConditionsOperation in experiment
54% With tetrabutylammomium bromide;bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; water; at 100℃; for 1h;Microwave irradiation; a) 2-(8-Oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)-oxazole-4-carboxylic acid ethyl ester<strong>[460081-18-9]2-Chloro-oxazole-4-carboxylic acid ethyl ester</strong> (50mg, 0.28 mmol), prepared according to Hodgetts and Kershaw, 2002, 7-(4,4,5,5-Tetramethyl-[l,3,2]dioxaborolan-2-yl)-3,4- dihydro-2H-naphthalen-l-one (94mg, 0.36 mmol), tetrabutylammonium bromide (lOmg, 0.04 mmol) and Pd(PPh3)2Cl2 (13mg, 0.02 mmol) in dioxane:water (1.2 mL/0.6 mL) were heated at 1000C in a microwave reactor for 1 hour. After this time, water and ethyl acetate were added and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were washed with water and brine and dried over Na2SO4. Concentration afforded a brown solid which was triturated with Et2O. The product was obtained as an off-white solid (43mg, 54%). NMR 1H (CDCl3, ppm): 8.72 (s, IH), 8.31 (s, IH), 8.28 (dd, IH), 7.41 (d, IH), 4.45 (q, 2H), 3.07-3.03 (m, 2H), 2.75-2.71 (m, 2H), 2.25-2.16 (m, 2H), 1.44 (t, IH).
  • 4
  • [ 856013-04-2 ]
  • [ 1135871-91-8 ]
  • [ 1135871-90-7 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;bis-triphenylphosphine-palladium(II) chloride; tetrabutylammomium bromide; In 1,4-dioxane; water; at 100℃; for 1h;Microwave irradiation; c) 6-(8-Oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)-pyridine-2-sulfonamide6-Bromo-pyridine-2-sulfonamide (65mg, 0.27 mmol), 7-(4,4,5,5-Tetramethyl- [l,3,2]dioxaborolan-2-yl)-3,4-dihydro-2H-naphthalen-l-one (97mg, 0.36 mmol), tetrabutylammonium bromide (TBAB) (lOmg, 0.04 mmol) and Pd(PPh3)2Cl2 (13mg, 0.02 mmol) in dioxane:water (1.2 mL/0.6 mL) were heated at 1000C in a microwave reactor for 1 hour. After this time, water was added and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were washed with water and brine and dried over Na2SO4. Concentration afforded a brown solid which was triturated with Et2O. An off-white solid was obtained. Analysis (NMR) showed presence of impurities but the compound was on-reacted without further purification. NMR 1H (d6-DMSO, ppm): 8.6 (d, J = 2.1 Hz, IH), 8.36 (dd, J = 8.1 and 2.1 Hz, IH), 8.20 (dd, J = 9.03 and 1 Hz, IH), 8.11 (t, J = 7.6 Hz, IH), 7.85 (dd, J = 7.6 and 1 Hz, IH), 7.53-7.50 (m, 3H), 3.01-2.98 (m, 2H), 2.66-2.62 (m, 2H), 2.10-2.04 (m, 2H).
  • 5
  • [ 41731-52-6 ]
  • [ 1135871-91-8 ]
  • [ 1135872-17-1 ]
YieldReaction ConditionsOperation in experiment
22% a) 2-(8-Oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)-thiazole-4-carboxylic acid ethyl esterl-Tetralone-7-boronic acid pinacol ester (250mg, 0.92 mmol), 2-chlorothiazole-4- carboxylic acid ethyl ester (153mg, 0.80 mmol), tetrabutylammoniumborohydride (25mg, 0.085 mmol), potassium carbonate (295mg, 2.14 mmol) and trans- dichlorobis(triphenylphosphine)palladium(II) (27mg, 0.038 mmol) were dissolved in dioxane (4 mL) and water (2 mL). Under microwave conditions (120W) the solution was heated at 1000C for 2 hours. After cooling the reaction mixture was poured into a water/ethyl acetate mixture (100 mL). After extraction, the aqueous layer was acidified with 2N hydrochloric acid (pH~3) to give a white precipitate which was collected by filtration to give the desired product (62mg, 22%). 1H NMR (CDCl3) delta (ppm):1.41 (t, 3H), 2.16 (m, 2H), 2.69 (t, 2H), 3.00 (t, 2H), 4.43 (q, 2H), 7.35 (d, IH), 8.15 (s, IH), 8.25 (dd, IH), 8.49 (s, IH).
  • 6
  • [ 1135871-91-8 ]
  • [ 460081-20-3 ]
  • [ 1135872-20-6 ]
  • 7
  • [ 149849-92-3 ]
  • [ 1135871-91-8 ]
  • [ 1445800-33-8 ]
  • 8
  • [ 75693-15-1 ]
  • [ 1135871-91-8 ]
  • 2-(2-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)-2,3,4,5-tetrahydrobenzo[b]oxepin-8-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; potassium acetate / 1,4-dioxane / 90 °C / Inert atmosphere 2: 1,1'-(phenyl-l3-iodanediyl)bis(pyridinium)trifluoromethanesulfonate / dichloromethane / -25 °C / Molecular sieve; Inert atmosphere
  • 9
  • [ 75693-15-1 ]
  • [ 1135871-91-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium acetate; bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 90 °C / Inert atmosphere 2: 1,1'-(phenyl-l3-iodanediyl)bis(pyridinium)trifluoromethanesulfonate; acetic acid / 1,2-dichloro-ethane / 3.5 h / 60 °C / Inert atmosphere; Molecular sieve
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