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[ CAS No. 741699-47-8 ] {[proInfo.proName]}

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Chemical Structure| 741699-47-8
Chemical Structure| 741699-47-8
Structure of 741699-47-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 741699-47-8 ]

CAS No. :741699-47-8 MDL No. :MFCD22414468
Formula : C14H21BO4 Boiling Point : -
Linear Structure Formula :- InChI Key :SYFCCAMEIIUWCU-UHFFFAOYSA-N
M.W : 264.13 Pubchem ID :23134192
Synonyms :

Calculated chemistry of [ 741699-47-8 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.57
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 75.38
TPSA : 47.92 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.35 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.2
Log Po/w (WLOGP) : 1.36
Log Po/w (MLOGP) : 0.82
Log Po/w (SILICOS-IT) : 1.62
Consensus Log Po/w : 1.2

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.83
Solubility : 0.388 mg/ml ; 0.00147 mol/l
Class : Soluble
Log S (Ali) : -2.84
Solubility : 0.381 mg/ml ; 0.00144 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.97
Solubility : 0.028 mg/ml ; 0.000106 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.04

Safety of [ 741699-47-8 ]

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 [ 741699-47-8 ]

* 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 [ 741699-47-8 ]

[ 741699-47-8 ] Synthesis Path-Downstream   1~20

  • 1
  • [ 741699-47-8 ]
  • [ 124-63-0 ]
  • [ 741699-48-9 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 20.0℃; for 1.0h; Reference Example 43 2-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]-ethyl methanesulfonate Methanesulfonyl chloride (0.33mL) was added to a mixture of 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenoxy]ethanol (0.92g) and triethylamine (0.73mL) in methylene chloride (18mL), and the mixture was stirred at room temperature for 1hr. 1mol/L hydrochloric acid was added to the reaction mixture. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to afford the title compound (1.28g). 1H-NMR(CDCl3)delta ppm: 1.34 (12H, s), 2.87 (3H, s), 3.21 (2H, t, J=6.9Hz), 4.45 (2H, t, J=6.9Hz), 7.29 (2H, d, J=7.5Hz), 7.64 (2H, d, J=7.5Hz)
With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 0.5h;Cooling; Step C: 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethyl methanesulfonate To a solution of <strong>[741699-47-8]2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethanol</strong> (200 mg, 0.76 mmol) and ehyldiisopropylamine (293 mg, 2.27 mol) in dichloromethane (10.0 mL) was added methanesulfonyl chloride (105 mg, 0.91 mmol) under cooling, and the mixture was stirred at 0 C. for 30 minutes. The mixture was quenched with cold water (10.0 mL), the organic layer was washed with sodium bicarbonate solution (10.0 mL*3) and brine (10.0 mL*3), dried over anhydrous saturated sodium sulfate, filtered and concentrated in vacuo to afford (2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethyl methanesulfonate which was used for next step directly.
With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 0.5h; To a solution of <strong>[741699-47-8]2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethanol</strong> (200 mg, 0.76 mmol) and ehyldiisopropylamine (293 mg, 2.27 mol) in dichloromethane (10.0 mL) was added methanesulfonyl chloride (105 mg, 0.91 mmol) under cooling, and the mixture was stirred at 0 oC for 30 minutes. The mixture was quenched with cold water (10.0 mL), the organic layer was washed with sodium bicarbonate solution (10.0 mL x 3) and brine (10.0 mL x 3), dried over anhydrous saturated sodium sulfate, filtered and concentrated in vacuo to afford (2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethyl methanesulfonate which was used for next step directly.
  • 2
  • [ 269410-28-8 ]
  • [ 741699-47-8 ]
YieldReaction ConditionsOperation in experiment
93% With sodium tetrahydroborate; ethanol; In tetrahydrofuran; at 20.0℃; for 2.0h;Cooling with ice; Step B: methyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethanol To a solution of ethyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)acetate (1 g, 3.27 mmol) in tetrahydrofuran/ethanol (10 mL/10 mL) was added sodium borohydride (124 mg, 3.27 mmol) under ice-water bath. The mixture was allowed to warm to room temperature and stirred for 2 hours. The mixture was partitioned between ethyl acetate (100 mL) and water (50 mL). The organic layer was separated, washed with brine (20 mL*3), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give methyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethanol (0.8 g, 93%) as colorless oil.
93% With sodium tetrahydroborate; ethanol; In tetrahydrofuran; at 20.0℃; for 2.0h;Cooling with ice; To a solution of ethyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)phenoxy)acetate (1 g, 3.27 mmol) in tetrahydrofuran/ethanol (10 mL/10 mL) was added sodium borohydride (124 mg, 3.27 mmol) under ice-water bath. The mixture was allowed to warm to room temperature and stirred for 2 hours. The mixture was partitioned between ethyl acetate (100 mL) and water (50 mL). The organic layer was separated, washed with brine (20 mL x 3), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give methyl 2- (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethanol (0.8 g, 93%) as colorless oil.
Reference Example 41 2-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]-ethanol Sodium borohydride (0.33g) was added to a mixture of ethyl [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]-acetate (1.33g), tetrahydrofuran (10mL) and ethanol (10mL). The mixture was stirred at room temperature for 4hrs, and water was added. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1) to afford the title compound (1.13g). 1H-NMR(CDCl3)delta ppm: 1.34 (12H, s), 2.01 (1H, t, J=6.3Hz), 3.90-4.00 (2H, m), 4.10-4.15 (2H, m), 6.91 (2H, d, J=8.7Hz), 7.76 (2H, d, J=8.7Hz)
YieldReaction ConditionsOperation in experiment
96% With toluene-4-sulfonic acid; In methanol; at 20.0℃; for 2.5h; General procedure: (5b) Benzyl 4-(2-hydroxyethoxy)piperidine-1-carboxylate[0094] Benzyl 4- [2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]piperidine-1-carboxylate (45.6 g, 125 mmol) produced in Reference Example 5 (5a) was dissolved in methanol, to which p-toluenesulfonic acid monohydrate (11.9 g, 62.7 mmol) was added, followed by stirring at room temperature for 2.5 hours. Sodium bicarbonate (powder) was added to the reaction liquid and the solvent was distilled off under reduced pressure. A solid precipitated, which was filtered off while washing with ethyl acetate. The filtrate was then concentrated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (hexane : ethyl acetate, 60 : 40 - 0 : 100, V/V) to give the desired title compound (29.1 g, yield 83%).1H-NMR (CDCl3)˜: 1.52-1.60 (2H, m), 1.82-1.90 (2H, m), 1.98 (1H, t, J = 6.0 Hz), 3.18-3.24 (2H, m), 3.50-3.55 (1H, m), 3.58 (3H, t, J = 4.6 Hz), 3.73 (2H, dt, J = 6.0, 4.6 Hz), 3.79-3.86 (2H, m), 5.13 (2H, s), 7.29-7.38 (5H, m) .
  • 4
  • [ 741699-47-8 ]
  • [ 160313-69-9 ]
  • ethyl 4'-(2-hydroxyethoxy)-2-methylbiphenyl-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate;1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80.0℃; Reference Example 42; Ethyl 4'-(2-hydroxyethoxy)-2-methylbiphenyl-4-carboxylate; A mixture of 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxa-borolan-2-yl)phenoxy]ethanol (0.2g), ethyl 4-bromo-3-methylbenzoic acid (0.276g), [1,1'-bis(diphenylphosphino)-ferrocene]dichloropalladium(II) (0.017g), [1,1'-bis-(diphenylphosphino)ferrocene] (0.013g) and tripotassium phosphate (0.643g) in 1,4-dioxane (5mL) was stirred at 80C overnight under an atmosphere of argon. Water and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/2) to afford the title compound (0.136g).
  • 5
  • [ 741699-47-8 ]
  • [ 98-59-9 ]
  • 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]ethyl benzenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With dmap; triethylamine; In dichloromethane; at 20.0℃; for 2.0h; (8c) 2-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]ethyl benzenesulfonate Into dichloromethane (100 mL), <strong>[741699-47-8]2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]ethanol</strong> (4.41 g, 16.7 mmol) synthesized in Example 8 (8b) was dissolved, to which triethylamine (4.62 mL, 33.2 mmol), 4-dimethylaminopyridine (400 mg, 3.27 mmol), and p-toluenesulfonyl chloride (4.80 g, 25.2 mmol) were sequentially added while ice cooling. The resulting mixture was warmed back to room temperature and stirred for a further two hours. The resulting reaction liquid was sequentially washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (hexane : ethyl acetate, 100 : 0 - 70 : 30, V/V) to give the desired title compound (6.1 g, yield 88%). 1H-NMR (CDCl3) delta: 1.33 (12H, s), 2.44 (3H, s), 4.16 (2H, t, J = 4.7 Hz), 4.37 (2H, t, J = 4.7 Hz), 6.75 (2H, d, J = 8.4 Hz), 7.33 (2H, d, J = 8.4 Hz), 7.70 (2H, d, J = 8.4 Hz), 7.81 (2H, d, J = 8.4 Hz).
  • 6
  • [ 269409-70-3 ]
  • [ 741699-47-8 ]
  • 7
  • [ 741699-47-8 ]
  • 2-(2,6-dioxopiperidin-3-yl)-5-(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethoxy)isoindoline-1,3-dione [ No CAS ]
  • 8
  • [ 741699-47-8 ]
  • (3R)-N-(3-(5-(4-(2-(2-(2,6 dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yloxy)ethoxy)phenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl)-3-fluoropyrrolidine-1-sulfonamide [ No CAS ]
  • 9
  • [ 741699-47-8 ]
  • C24H18ClFO2S [ No CAS ]
  • C32H27FO4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
150 mg With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; at 100.0℃; In Step 1, 500 mg 71 was alkylated with 2-bromoethanol in the presence of K2CO3 in DMF at 80 C. to provide 500 mg of 72 after purification. In Step 2, 100 mg of 72 was borylated to afford 100 mg of 73 after purification. In Step 3, 240 mg of 52 was alkylated with benzyl bromide in the presence of sodium hydride in DMF to provide 250 mg of 53 after purification. In Step 4, 550 mg of 73 and 1.1 g of 53 was reacted in the presence of Pd(PPh3)4 and K2CO3 in toluene and water at 100 C. to provide 150 mg of Compound 12 after purification. In Step 5, 20 mg of Compound 125 was reacted with tosyl chloride and triethylamine in dichloromethane to provide 19 mg of 75 after purification. In Step 6, 17 mg of 75 was reacted with crude 3-(fluoromethyl)azetidine (prepared by deprotection of tert-butyl 3-(fluoromethyl)azetidine-1-carboxylate with trifluoroacetic acid in dichloromethane) in the presence of K2CO3 in acetonitrile to provide Compound 120.
  • 10
  • [ 741699-47-8 ]
  • 5-iodo-7-phenyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one [ No CAS ]
  • C20H17N3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
27% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 120.0℃;Inert atmosphere; Microwave irradiation; General procedure: A mixture of 5-iodo-7-phenyl-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one (CH4) (180 mg, 0.534 mmol), 2-(4-(2-methoxyethoxy)phenyl-4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane (186 mg, 0.667 mmol) (commercial source), Pd(dppf)Cl2 (43.6 mg, 0.053 mmol) and K2CO3 (148 mg, 1 .07 mmol) in 1 ,4-dioxane:H20 (3 ml_, 9:1) was de-oxygenated for 5 min then heated in a microwave reactor at 120C for a total of 90 min. The reaction was repeated on the same scale with heating in a microwave reactor for 2 h. The reaction mixture were filtered through celite and washed with methanol. The combined organics were concentrated in vacuo. The crude solid was diluted with DCM (25 ml_) and H2O (25 ml_) and the layers separated via a phase separator. The combined organics were concentrated in vacuo. The crude solid was purified by silica gel chromatography eluting with 0-7.5% MeOH/DCM, followed by reversed phase preparative HPLC-MS. A final purification using silica gel chromatography was carried out by eluting with 0-5% MeOH/DCM to afford 5-[4-(2-methoxy-ethoxy)-phenyl]-7-phenyl-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one (Ex-58) as a white solid (70 mg, 18%); LC-MS. Rt 7.66 min, AnalpH2_MeOH_QC_V1 (1); (ESI+) m/z 362.2 [M+H]+; NMR (400 MHz, DMSO-c/6): 12.13 (br s, 1 H), 7.95 (s, 1 H), 7.93 (d, J = 8.8 Hz, 2H), 7.78- 7.75 (m, 2H), 7.73 (s, 1 H), 7.58-7.55 (m, 2H), 7.42 (tt, J = 7.6, 1 .3 Hz, 1 H), 6.95 (d, J = 8.8 Hz, 2H), 4.13-4.1 1 (m, 2H), 3.69-3.66 (m, 2H), 3.32 (s, 3H).
  • 11
  • [ 741699-47-8 ]
  • (8-chloro-3-methoxy-2-quinolyl) trifluoromethanesulfonate [ No CAS ]
  • 2-[4-(8-chloro-3-methoxy-2-quinolyl)phenoxy]ethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
70.5% With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In water; toluene; at 100.0℃; for 16.0h;Inert atmosphere; A mixture of (8-chloro-3-methoxy-2-quinolyl) trifluoromethanesulfonate (400 mg, 1.17 mmol), 2-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenoxy)ethanol (340 mg, 1.29 mmol), Pd(PtoP)4 (67.6 mg, 58.5 m mol) and CS2CO3 (458 mg, 1.4 mmol) in toluene (15 mL) and water (3mL) was charged with N2 and then stirred at l00C for 16 hours. After cooling, the mixture was diluted with EtOAc (50 mL) and washed with water (10 mL). The organic layer was separated out and concentrated in vacuo, the residue was purified by column chromatography on silica gel (elution with PE : EtOAc 100:10 to 100:50) to give 2-[4-(8-chloro-3-methoxy-2- quinolyl)phenoxy]ethanol (0.27 g, 70.5 %) as an off-white oil. MS obsd. (ESI+) [(M+H)+]:330.0.
  • 12
  • [ 741699-47-8 ]
  • (8-chloro-2-quinolyl) trifluoromethanesulfonate [ No CAS ]
  • 2-[4-(8-chloro-2-quinolyl)phenoxy]ethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In water; toluene; at 100.0℃; for 3.0h;Inert atmosphere; Microwave irradiation; A mixture of (8-chloro-2-quinolyl) trifluoromethanesulfonate (500 mg, 1.6 mmol), 2-[4- (4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenoxy]ethanol (424 mg, 1.6 mmol), Pd(Ph3P)4 (55.6 mg, 48.1 m mol) and CS2CO3 (627 mg, 1.93 mmol) in toluene (5 mL) and water (1 mL) was charged with N2 and stirred at 100 C under microwave condition for 3 hours. After the reaction was completed, the mixture was diluted with water (10 mL) and extracted with EtOAc (25 mL) three times. The combined organic layer was washed with brine, dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (elution with PE : EtOAc 10:1- 2:1) to give 2-[4-(8-chloro-2-quinolyl)phenoxy]ethanol (202 mg, 42%) as a light yellow solid. MS obsd. (ESI+) [(M+H)+]:299.7
  • 13
  • [ 741699-47-8 ]
  • 2-bromo-7-(trifluoromethyl)quinoline [ No CAS ]
  • 2-[4-[7-(trifluoromethyl)-2-quinolyl]phenoxy]ethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
85.2% With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In water; toluene; at 100.0℃; for 3.0h;Inert atmosphere; Microwave irradiation; A mixture of 2-bromo-7-(trifluoromethyl)quinoline (CAS : 1352443-02-7, Cat.: SY046186, from Accela ChemBio Inc, 200 mg, 724 m mol), 2-(4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)phenoxy)ethanol (191 mg, 724 m mol), Pd(Ph3P)4 (25.1 mg, 21.7 miho) and CS2CO3 (354 mg, 1.09 mmol) in the mixed solvent of toluene (5 mL) and water (1 mL) was charged with N2 and stirred at 100 C under microwave condition for 3 hours. After the reaction was completed, the mixture was diluted with water (10 mL) and extracted with EtOAc (25 mL) three times. The combined organic layer was washed with brine, dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (elution with PE : EtOAc 10: 1- 2: 1) to give 2-[4-[7-(trifluoromethyl)-2- quinolyl]phenoxy]ethanol (2l0mg, 85.2%) as a light grey solid. 1 H NMR (METHANOL-<74, 400MHz): d ppm 8.46 (d, J = 8.68 Hz, 1 H), 8.39 (s, 1 H), 8.18 - 8.23 (m, 2 H), 8.11 - 8.17 (m, 2 H), 7.77 (dd, J = 8.50, 1.65 Hz, 1 H), 7.14 - 7.20 (m, 2 H), 4.15 - 4.21 (m, 2 H), 3.92 - 3.98 (m, 2 H). MS obsd. (ESE) [(M+H)+]: 333.5.
  • 14
  • [ 741699-47-8 ]
  • 2-[4-(8-chloro-2-quinolyl)phenoxy]ethyl trifluoromethanesulfonate [ No CAS ]
  • 15
  • [ 741699-47-8 ]
  • cis-methyl 3-[2-[4-(8-chloro-2-quinolyl)phenoxy]ethoxy]cyclobutanecarboxylate [ No CAS ]
  • 16
  • [ 741699-47-8 ]
  • cis-3-[2-[4-(8-chloro-2-quinolyl)phenoxy]ethoxy]cyclobutanecarboxylic acid [ No CAS ]
  • 17
  • [ 741699-47-8 ]
  • 2-[4-[7-(trifluoromethyl)-2-quinolyl]phenoxy]ethyl trifluoromethanesulfonate [ No CAS ]
  • 18
  • [ 741699-47-8 ]
  • cis-methyl 3-[2-[4-[7-(trifluoromethyl)-2-quinolyl]phenoxy]ethoxy]cyclobutanecarboxylate [ No CAS ]
  • 19
  • [ 34743-88-9 ]
  • [ 73183-34-3 ]
  • [ 741699-47-8 ]
YieldReaction ConditionsOperation in experiment
81.4% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In dimethyl sulfoxide; at 90.0℃; for 4.0h;Inert atmosphere; A mixture of 2-(4-bromophenoxy) ethanol (CAS : 24743-88-9, Cat.: SY02949, from Accela ChemBio Inc, 4.34 g, 20 mmol), bis(pinacolato)diboron (5.59 g, 22 mmol), PdCl2(DPPF)-CH2Cl2 adduct (439 mg, 600 m mol) and potassium acetate (5.89 g, 60 mmol) in DMSO (50 mL) was stirred at 90 C under nitrogen atmosphere for 4 hours. The mixture was then diluted with EtOAc (300 mL) and washed with water (100 mL) twice, brine (100 mL) in sequence. The organic layer was separated out and concentrated in vacuo, the residue was purified by column chromatography on silica gel (elution with PE : EtOAc 10:1- 2:1) to give 2- [4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenoxy]ethanol (4.3 g, 81.4% yield) as a light yellow oil. MS obsd. (ESI+) [(M+H)+]:265.l.
  • 20
  • [ 741699-47-8 ]
  • [ 1403993-19-0 ]
  • (R)-2-(4-(5-(1-(quinuclidin-3-yl)-1H-1,2,3-triazol-4-yl)thiophen-2-yl)phenoxy)ethan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; at 150.0℃; for 0.25h;Inert atmosphere; Microwave irradiation; Sealed tube; General procedure: To a mixture of derivative of type IV (50 mg, 0.147 mmol) intoluene (1.5 mL) and EtOH (0.75 mL) were successively added thedesired boronic ester or acid of type V (0.176 mmol, 1.2 eq.), K2CO3(0.294 mmol, 2.0 eq.) and Pd(PPh3)4 (0.0147 mmol, 10 mol %). Thereaction mixture was degassed with Ar and irradiated under microwavefor 20 min at 150 C. Alternatively PdCl2(dppf) 10 mol %,could be used as catalyst. In this case the base was switched toNa2CO3 (2.0 eq.) and the irradiation performed for 40 min at 100 C.In both cases, after cooling, the volatiles were removed underreduced pressure and the crude material purified by flash chromatography(CH2Cl2/MeOH 80/20 NH4OH 0.1 mL).
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