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[ CAS No. 852227-96-4 ] {[proInfo.proName]}

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Chemical Structure| 852227-96-4
Chemical Structure| 852227-96-4
Structure of 852227-96-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 852227-96-4 ]

CAS No. :852227-96-4 MDL No. :MFCD07368524
Formula : C17H26BNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :OTOKWHGMHAAFRM-UHFFFAOYSA-N
M.W : 287.20 Pubchem ID :4961250
Synonyms :

Calculated chemistry of [ 852227-96-4 ]

Physicochemical Properties

Num. heavy atoms : 21
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.65
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 92.37
TPSA : 21.7 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.3 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 3.88
Log Po/w (WLOGP) : 2.6
Log Po/w (MLOGP) : 2.42
Log Po/w (SILICOS-IT) : 2.45
Consensus Log Po/w : 2.27

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.14
Solubility : 0.0206 mg/ml ; 0.0000717 mol/l
Class : Moderately soluble
Log S (Ali) : -4.03
Solubility : 0.0266 mg/ml ; 0.0000926 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.71
Solubility : 0.00554 mg/ml ; 0.0000193 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.93

Safety of [ 852227-96-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P302+P352-P305+P351+P338-P330-P362-P403+P233-P501 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 852227-96-4 ]

* 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 [ 852227-96-4 ]

[ 852227-96-4 ] Synthesis Path-Downstream   1~22

  • 1
  • [ 22148-20-5 ]
  • [ 73183-34-3 ]
  • [ 852227-96-4 ]
YieldReaction ConditionsOperation in experiment
90% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium hydrogencarbonate In tetrahydrofuran; water at 80℃; for 0.166667h; Microwave irradiation; Inert atmosphere;
86% With potassium acetate In dimethyl sulfoxide at 60℃; for 20.5h; 62.a To a solution of 1-(4-bromophenyl)piperidine (250 mg, 1.04 mmol) in DMSO (6 mL) was added bis-pinacolatodiboron (314 mg, 1.24 mmol) and KOAc (306 mg, 3.12 mmol). The reaction was degassed under vacuum for 30 min. then the flask was flushed N2 (g). PdCl2dppf (85 mg, 0.104 mmol) was added, then the reaction was heated to 60° C. for 20 h. Upon cooling, the reaction was then diluted with methylene chloride (50 mL) and washed with a 5% LiCl solution (4×). The organics were dried (Na2SO4), filtered, and concentrated. Purification by flash chromatography (12 g ISCO column, methylene chloride/[MeOH/NH4OH 10:1)], 100:0 to 85:15) gave the title compound (262 mg, 86%) as a white powder: ESI MS m/z 288 [M+H]+.
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; dichloromethane at 80℃; for 12h;
With 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex; potassium acetate In N,N-dimethyl-formamide

  • 3
  • [ 851684-46-3 ]
  • [ 852227-96-4 ]
  • [ 1432450-89-9 ]
YieldReaction ConditionsOperation in experiment
41.4% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; ethanol at 80℃; for 12h;
  • 4
  • [ 852227-96-4 ]
  • [ 876754-63-1 ]
  • [ 1565835-37-1 ]
YieldReaction ConditionsOperation in experiment
80% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium hydrogencarbonate In water; N,N-dimethyl-formamide at 80℃; for 0.166667h; Microwave irradiation; Inert atmosphere;
  • 5
  • [ 852227-96-4 ]
  • [ 876754-66-4 ]
  • [ 1565835-39-3 ]
YieldReaction ConditionsOperation in experiment
70% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium hydrogencarbonate In water; N,N-dimethyl-formamide at 80℃; for 0.166667h; Microwave irradiation; Inert atmosphere;
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 70℃; for 4h; Inert atmosphere; 4 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) General procedure: A mixture of 4-(4-bromophenyl)~2-methylmorphoiine (8 g, ~31 mmol), 4,4,4 i4l,5,5,5i,5 -octamethyl-2,2 -bi(1 , ,2-dioxaborolane) (10.3 g, 40.6 mmol), KOAc (4.6 g, 46.5 mmoi) and PdCI2 (dppf (2.26 g, 3.1 mmol) in DMSO (80 mL) was heated at 70 °C under N2 for 4 hours. The reaction mixture was partitioned with EA and water. The combined organic phase was dried and concentrated, purification over silica gel chromatography, eluting with EA PE = 5:1 , to give product as light yellow solid. MS (m/z): 304 (M+H)•.
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃; for 16h; 169 General procedure: A mixture of Compound 27B (1.35 g, 5.4mmol), Pd(dppf)C12 (0.35 g, 0.43 mmol), 4,4,4,4,5,5,5’, 5’-octamethyl-2,2’-bi( 1,3 ,2-dioxaborolane) (2.09 g, 8.22 mmol), and potassium acetate (1.62 g, 16.5 mmol) in 1,4-dioxane (50 ml) was heated at 80°C for 16 hours. The mixture was diluted with water (200 mL) and extracted with ethyl acetate (200 mL x 2). The combined extracts were washed with water (200 mL) and brine (200 mL), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, from 0% to 10% v/v) to furnish Compound 27C. LC-MS (ESI) m/z: non-ionizable compound under routine conditions used.
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃; for 16h; 169 General procedure: A mixture of Compound 27B (1.35 g, 5.4mmol), Pd(dppf)Cl2 (0.35 g, 0.43 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (2.09 g, 8.22 mmol), and potassium acetate (1.62 g, 16.5 mmol) in 1,4-dioxane (50 ml) was heated at 80 o C for 16 hours. The mixture was diluted with water (200 mL) and extracted with ethyl acetate (200 mL x 2). The combined extracts were washed with water (200 mL) and brine (200 mL), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, from 0% to 10% v/v) to furnish Compound 27C. LC-MS (ESI) m/z: non-ionizable compound under routine conditions used.
  • 7
  • [ 852227-96-4 ]
  • 1-(4-[18F]fluorophenyl)piperidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(pyridine)copper(II) bis(trifluoromethanesulfonate); N,N-dimethyl-formamide In acetonitrile at 110℃; for 0.333333h; Sealed tube;
  • 8
  • [ 76-09-5 ]
  • C17H18BNO2 [ No CAS ]
  • [ 852227-96-4 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In 1,2-dichloro-ethane at 20℃; Schlenk technique; Inert atmosphere; General Procedure for Catalytic Arene Borylation: General procedure: In a 20 mL Schlenk tube under Ar, B(C6F5)3 (51.2 mg, 0.10 mmol) was dissolved in distilled1,2-dichloroethane (2 mL), followed by the addition of catecholborane (2, 117 μL, 1.1 mmol) andtetrahydrothiophene (9 μL, 0.10 mmol). Then, to the mixture was added the arene substrate (1.0mmol), and the resulting mixture was heated to 80 °C (oil bath temp.) and stirred for the appropriatereaction time. After cooling to room temperature, excess Et3N (2 mL, ca. 15 mmol) and then, pinacol(355 mg, 3 mmol) were added to the reaction mixture and stirred. The reaction mixture wasquenched by aqueous NH4Cl, extracted with EtOAc, washed with brine, and dried over Na2SO4.Purification by silica gel column chromatography (eluent: CH2Cl2/hexane) was performed to affordthe borylated products.
  • 9
  • [ 4096-20-2 ]
  • [ 852227-96-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tris(pentafluorophenyl)borate; thiophene / 1,2-dichloro-ethane / 24 h / 80 °C / Schlenk technique; Inert atmosphere 2: triethylamine / 1,2-dichloro-ethane / 20 °C / Schlenk technique; Inert atmosphere
  • 10
  • [ 852227-96-4 ]
  • methyl 4-((2-bromo-N-methyl-5-((4-(piperidin-1-ylmethyl)benzyl)carbamoyl)thiophene)-3-sulfonamido)benzoate [ No CAS ]
  • methyl 4-((N-methyl-2-(4-(piperidin-1-yl)phenyl)-5-((4-(piperidin-1-ylmethyl)benzyl)carbamoyl)thiophene)-3-sulfonamido)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 90℃; for 1h; Inert atmosphere; 3b Example 3b - Synthesis of compound 2 (methyl 4-((N-methyl-2-(4-(piperidin-1-yl)phenyl)-5-((4-(piperidin-1-ylmethyl)benzyl)carbamoyl)thiophene)-3-sulfonamido)benzoate) Compound 33 (40 mg, 64.46 μιηοΙ, 1 eq.) was taken in a round bottom flask along with a solvent mixture (3.5 mL) of ethanol, toluene and water (9 : 3: 1). l-(4-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)phenyl)piperidine (22.21 mg, 77.35 μιηοΙ, 1.2 eq.) and K2CO3 (26.72 mg, 193.37 μιηοΙ, 3 eq.) were added to the solution. Tetrakis (triphenylphosphine) palladium (7.45 mg, 6.45 μιηοΙ, and 0.10 eq.) was then added under N2 and the solution was stirred for 1 hour at 90 °C at which point TLC and LC-MS showed completion of the reaction. The solution was quenched with water and the water layer was extracted with DCM (x 3). The combined organic layer was dried with MgS04 and the product, 2, was purified by column chromatography (using dichloromethane: diethyl ether 1 : 1) as a yellow solid with 70% yield. (0184) FT-IR (Neat) : v (cm"1) = 2925, 2854, 1736, 1720, 1698, 1693, 1655, 1650, 1638, 1631, 1604, 1572, 1561, 1537, 1519, 1509, 1461, 1440, 1346, 1247, 1231, 1178; 1H-NMR (400 MHz, CDCI3) : δ ppm 7.78 - 7.84 (m, 2H), 7.61 (s, 1H), 7.32 - 7.34 (m, 2H), 7.28 - 7.31 (m, 4H), 6.98 - 7.01 (m, 2H), 6.72 - 6.78 (m, 2H), 6.26 (br. s., NH), 4.58 (d, J = 5.54 Hz, 2H), 3.91 (s, 3H), 3.50 (s, 2H), 3.20 - 3.26 (m, 4H), 2.99 (s, 3H), 2.37 - 2.43 (m, 4H), 1.61 - 1.73 (m, 8H), 1.55 - 1.61 (m, 4H); 13C-NMR (100 MHz, CDCI3) : δ 166.25, 160.00, 152.64, 146.38, 144.01, 138.36, 137.51, 135.99 (2C), 131.84, 131.15, 130.09 (2C), 129.79, 129.42, 127.91, 127.45, 125.51, 125.23, 124.22, 114.41 (2C), 114.18 (2C), 63.31, 54.38, 54.13, 52.12, 51.52, 49.13, 43.96, 37.52, 32.03, 30.31, 29.69, 25.80, 25.48, 24.27; HRMS-ESI (m/z) : calcd. for C36H44N4O5S2 = 700.2753, found = 700.2815.
  • 11
  • [ 852227-96-4 ]
  • 5-bromo-4-(N-(4-(methoxycarbonyl)phenyl)-N-methylsulfamoyl)thiophene-2-carboxylic acid [ No CAS ]
  • 4-(N-(4-(methoxycarbonyl)phenyl)-N-methylsulfamoyl)-5-(4-(piperidin-1-yl)phenyl)thiophene-2-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 100℃; for 0.333333h; Microwave irradiation; Inert atmosphere; 1.4; 4b.1; 5a.1 Step 4 - Synthesis of (f) (4-(N-(4-(methoxycarbonyl)phenyl)-N-methylsulfamoyl)-5-(4-(piperidin-1-yl)phenyl)thiophene-2-carboxylic acid) Compound (e) (50 mg, 115.13 μιηοΙ, 1 eq .) was taken in a microwave via l along with a solvent mixture (3 mL) of ethanol, toluene and water (9 : 3 : 1) . l-[4-(4,4,5,5-Tetramethyl- l,3,2-dioxaborolan-2-yl)phenyl]piperidine (39.68 mg, 138.16μη-ιοΙ, 1.2 eq .) and K2CO3 (47.74 mg, 345.40 μιηοΙ, 3 eq .) were added to the solution . Tetrakis (triphenylphosphine) palladium ( 13.30 mg, 11.51 μιηοΙ, 0.1 eq .) was then added under N2 and incubated in microwave irradiation at 100 °C for 20 minutes. The solution was quenched with water. The pH of the water layer was 11, 0.025 N HCI was added to the solution to make the pH 2/3; then the water layer was extracted with DCM (x 3) . The combined organic layer was dried with anhydrous MgS04 and the product, (f) was purified by column chromatography (Et20 with 1% methanol) as a yellow solid with 60% yield . FT-IR (Neat) : v (cm"1) = 2935, 2360, 1714, 1603, 1439, 1279, 1114, 885, 773, 698; NMR (400 MHz, METHANOL-d) : δ ppm 7.86 (s, 1H), 7.77 (d, J = 8.8 Hz, 2H), 7.23 (d, J = 8.8 Hz, 2H), 7.07 (d, J = 8.8 Hz, 2H), 6.76 (d, J = 8.8 hz, 2H), 3.88 (s, 3H), 3.19 - 3.24 (m, 4H), 3.05 (s, 3H), 1.64 - 1.72 (m, 6H); 13C-NMR (100 MHz, METHANOL-d) : δ 163.89, 162.23, 150.66, 143.52, 142.11, 135.50, 134.19, 131.23, 130.67, 128.59, 128.34, 126.00, 119.84, 119.01, 113.60 (2C), 110.96, 110.61, 61.10 (2C), 52.94, 28.99, 25.81, 25.08, 22.41; HRMS- ESI (m/z) : calcd. for C25H26N2O6S2 = 514.1232, found = 514.1296.
  • 12
  • [ 852227-96-4 ]
  • 5-fluoro-3-methyl-2-(4-(4-(piperidin-1-yl)benzyl)phenyl)quinolin-4(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex; potassium phosphate / toluene / 10 h / 85 °C / Inert atmosphere 2: trifluorormethanesulfonic acid / butan-1-ol / 130 °C
  • 13
  • [ 852227-96-4 ]
  • [ 95889-09-1 ]
  • 1-(4-(4-(piperidin-1-yl)benzyl)phenyl)propan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate; 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex In toluene at 85℃; for 10h; Inert atmosphere;
  • 14
  • [ 852227-96-4 ]
  • C19H17BrClN3O4 [ No CAS ]
  • C30H31ClN4O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane at 80℃; Inert atmosphere; 406 Reference Example 4 [00515] Synthesis of 4-((4'-bromo-[l,l'-biphenyl]-4-yl)thio)-lH-l,2,3-triazole-5- carboxylic acid (4) General procedure: A mixture of (4-iodophenyl)(methyl)sulfane (Compound 4A) (500 mg, 2 mmol), 4-bromophenylboronic acid (400 mg, 2 mmol), Na2CCh (636 mg, 6 mmol), and Pd(PPh3)4 (115 mg, 0.1 mmol) in toluene/EtOH/H20 (20/10/4 mL) was stirred at 80 °C under nitrogen overnight The mixture was concentrated under reduced pressure. The residue was purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, 10% v/v) to afford Compound 4B. LC-MS (ESI) m/z: non-ionizable compound under routine conditions used. - NMR (CDCb, 500 MHz): d (ppm) 2.52 (s, 3H), 7.32 (d, J= 8.5 Hz, 2H), 7.43 (d, J= 8.5 Hz, 2H), 7.48 (d, J= 8.5 Hz, 2H), 7.55 (d, J= 8.5 Hz, 2H).
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane at 80℃; Inert atmosphere; 406 Synthesis of 4-((4'-bromo-[1,1'-biphenyl]-4-yl)thio)-1H-1,2,3-triazole-5- carboxylic acid (4) General procedure: A mixture of (4-iodophenyl)(methyl)sulfane (Compound 4A) (500 mg, 2 mmol), 4-bromophenylboronic acid (400 mg, 2 mmol), Na2CO3 (636 mg, 6 mmol), and Pd(PPh3)4 (115 mg, 0.1 mmol) in toluene/EtOH/H2O (20/10/4 mL) was stirred at 80 oC under nitrogen overnight. The mixture was concentrated under reduced pressure. The residue was purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, 10% v/v) to afford Compound 4B. LC-MS (ESI) m/z: non-ionizable compound under routine conditions used.1H- NMR (CDCl3, 500 MHz): d (ppm) 2.52 (s, 3H), 7.32 (d, J = 8.5 Hz, 2H), 7.43 (d, J = 8.5 Hz, 2H), 7.48 (d, J = 8.5 Hz, 2H), 7.55 (d, J = 8.5 Hz, 2H).
  • 15
  • [ 852227-96-4 ]
  • ethyl 5-((4-bromophenyl)thio)-1-(4-methoxybenzyl)-1H-1,2,3-triazole-4-carboxylate [ No CAS ]
  • C30H32N4O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 80℃; Inert atmosphere; 169 Reference Example 4 [00515] Synthesis of 4-((4'-bromo-[l,l'-biphenyl]-4-yl)thio)-lH-l,2,3-triazole-5- carboxylic acid (4) General procedure: A mixture of (4-iodophenyl)(methyl)sulfane (Compound 4A) (500 mg, 2 mmol), 4-bromophenylboronic acid (400 mg, 2 mmol), Na2CCh (636 mg, 6 mmol), and Pd(PPh3)4 (115 mg, 0.1 mmol) in toluene/EtOH/H20 (20/10/4 mL) was stirred at 80 °C under nitrogen overnight The mixture was concentrated under reduced pressure. The residue was purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, 10% v/v) to afford Compound 4B. LC-MS (ESI) m/z: non-ionizable compound under routine conditions used. - NMR (CDCb, 500 MHz): d (ppm) 2.52 (s, 3H), 7.32 (d, J= 8.5 Hz, 2H), 7.43 (d, J= 8.5 Hz, 2H), 7.48 (d, J= 8.5 Hz, 2H), 7.55 (d, J= 8.5 Hz, 2H).
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 80℃; Inert atmosphere; 169 Synthesis of 4-((4'-bromo-[1,1'-biphenyl]-4-yl)thio)-1H-1,2,3-triazole-5- carboxylic acid (4) General procedure: A mixture of (4-iodophenyl)(methyl)sulfane (Compound 4A) (500 mg, 2 mmol), 4-bromophenylboronic acid (400 mg, 2 mmol), Na2CO3 (636 mg, 6 mmol), and Pd(PPh3)4 (115 mg, 0.1 mmol) in toluene/EtOH/H2O (20/10/4 mL) was stirred at 80 oC under nitrogen overnight. The mixture was concentrated under reduced pressure. The residue was purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, 10% v/v) to afford Compound 4B. LC-MS (ESI) m/z: non-ionizable compound under routine conditions used.1H- NMR (CDCl3, 500 MHz): d (ppm) 2.52 (s, 3H), 7.32 (d, J = 8.5 Hz, 2H), 7.43 (d, J = 8.5 Hz, 2H), 7.48 (d, J = 8.5 Hz, 2H), 7.55 (d, J = 8.5 Hz, 2H).
  • 16
  • [ 852227-96-4 ]
  • ethyl 5-(4-bromophenoxy)-1-(4-methoxybenzyl)-1H-1,2,3-triazole-4-carboxylate [ No CAS ]
  • C30H32N4O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 80℃; Inert atmosphere; 221 Reference Example 4 [00515] Synthesis of 4-((4'-bromo-[l,l'-biphenyl]-4-yl)thio)-lH-l,2,3-triazole-5- carboxylic acid (4) General procedure: A mixture of (4-iodophenyl)(methyl)sulfane (Compound 4A) (500 mg, 2 mmol), 4-bromophenylboronic acid (400 mg, 2 mmol), Na2CCh (636 mg, 6 mmol), and Pd(PPh3)4 (115 mg, 0.1 mmol) in toluene/EtOH/H20 (20/10/4 mL) was stirred at 80 °C under nitrogen overnight The mixture was concentrated under reduced pressure. The residue was purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, 10% v/v) to afford Compound 4B. LC-MS (ESI) m/z: non-ionizable compound under routine conditions used. - NMR (CDCb, 500 MHz): d (ppm) 2.52 (s, 3H), 7.32 (d, J= 8.5 Hz, 2H), 7.43 (d, J= 8.5 Hz, 2H), 7.48 (d, J= 8.5 Hz, 2H), 7.55 (d, J= 8.5 Hz, 2H).
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 80℃; Inert atmosphere; 221 Synthesis of 4-((4'-bromo-[1,1'-biphenyl]-4-yl)thio)-1H-1,2,3-triazole-5- carboxylic acid (4) A mixture of (4-iodophenyl)(methyl)sulfane (Compound 4A) (500 mg, 2 mmol), 4-bromophenylboronic acid (400 mg, 2 mmol), Na2CO3 (636 mg, 6 mmol), and Pd(PPh3)4 (115 mg, 0.1 mmol) in toluene/EtOH/H2O (20/10/4 mL) was stirred at 80 oC under nitrogen overnight. The mixture was concentrated under reduced pressure. The residue was purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, 10% v/v) to afford Compound 4B. LC-MS (ESI) m/z: non-ionizable compound under routine conditions used.1H- NMR (CDCl3, 500 MHz): d (ppm) 2.52 (s, 3H), 7.32 (d, J = 8.5 Hz, 2H), 7.43 (d, J = 8.5 Hz, 2H), 7.48 (d, J = 8.5 Hz, 2H), 7.55 (d, J = 8.5 Hz, 2H).
  • 17
  • [ 852227-96-4 ]
  • 8-(3-bromo-5-chloropyridin-4-yl)-2,8-diazaspiro[4.5]decan-1-one [ No CAS ]
  • 8-(3-chloro-5-(4-(piperidin-1-yl)phenyl)pyridin-4-yl)-2,8-diazaspiro[4.5]decan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In water; acetonitrile at 120℃; for 1h; Microwave irradiation; Inert atmosphere;
  • 18
  • [ 852227-96-4 ]
  • C19H17BrClN3O3S [ No CAS ]
  • C30H31ClN4O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 80℃; Inert atmosphere; 342 Synthesis of 4-((4'-bromo-[1,1'-biphenyl]-4-yl)thio)-1H-1,2,3-triazole-5- carboxylic acid (4) General procedure: A mixture of (4-iodophenyl)(methyl)sulfane (Compound 4A) (500 mg, 2 mmol), 4-bromophenylboronic acid (400 mg, 2 mmol), Na2CO3 (636 mg, 6 mmol), and Pd(PPh3)4 (115 mg, 0.1 mmol) in toluene/EtOH/H2O (20/10/4 mL) was stirred at 80 oC under nitrogen overnight. The mixture was concentrated under reduced pressure. The residue was purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, 10% v/v) to afford Compound 4B. LC-MS (ESI) m/z: non-ionizable compound under routine conditions used.1H- NMR (CDCl3, 500 MHz): d (ppm) 2.52 (s, 3H), 7.32 (d, J = 8.5 Hz, 2H), 7.43 (d, J = 8.5 Hz, 2H), 7.48 (d, J = 8.5 Hz, 2H), 7.55 (d, J = 8.5 Hz, 2H).
  • 19
  • [ 4280-36-8 ]
  • [ 73183-34-3 ]
  • [ 852227-96-4 ]
YieldReaction ConditionsOperation in experiment
62% With tetramethylammonium fluoride; 2-mercaptopyridine sodium salt In acetonitrile at 30 - 35℃; for 24h; Irradiation; Inert atmosphere; General procedure for the photo-induced C-F borylation of fluoroarenes (GP1) General procedure: To a 9 mL snap vial with magnetic stirring bar, B2pin2 (0.6 mmol), TMAF (0.6 mmol), sodiumpyridine-2-thiolate (30 mol%) were added. The vial was evacuated and back filled with N2 for threetimes. A solution of fluoroarene (0.2 mmol) in dry MeCN (2 mL) was added by syringe. The mixturewas irradiated with a 385-390 nm LED (with aluminum block cooling to keep the internaltemperature of the reaction mixture at 30-35 oC) under N2 atmosphere. After 24 h, the reactionmixture was diluted with EA (5 mL) and filtered through a pad of Celite. After filtration, the filtratewas concentrated under reduced pressure. The residue was purified by silica gel columnchromatography (eluent: hexane/EtOAc) to give the corresponding boronate esters.
  • 20
  • [ 852227-96-4 ]
  • C20H33N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrahydrofuran; hexane / 1 h / 20 °C 2: copper(I) bromide / tetrahydrofuran; hexane / 20 °C
  • 21
  • [ 29786-93-4 ]
  • [ 852227-96-4 ]
  • C21H35BNO2(1-)*Li(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; hexane at 20℃; for 1h;
  • 22
  • [ 852227-96-4 ]
  • [ 19656-74-7 ]
  • C20H33N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% Stage #1: 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidine With n-butyllithium In tetrahydrofuran; hexane at 25℃; for 1h; Stage #2: N,N'-di-tert-butyldiaziridin-3-one With copper(II) bromide In tetrahydrofuran; hexane at 25℃; for 1h; 9 Example 9. Aromatic urea (see Structural Formula III-i): The arylboronic acid pinacol ester I-i (0.0862g, 0.30mmol) was added to the reaction vessel, 0.6mL of the first organic solvent tetrahydrofuran, n-butyl lithium (0.206mL, 0.33mmol, 1.6M in hexane), stirred at 25 °C for 1h; N,N-di-tert-butyldiaziridin-3-one II (0.0817g, 0.48mmol) was added therein, stirred at 25 °C for 10min; and then CuBr ( 0.0430g, 0.30 mmol) was added to the reaction vessel and the reaction was carried out at 25 °C for 1 h. Direct column chromatography, the specific conditions are: the column is loaded with petroleum ether, the eluent is a mixture of petroleum ether and ethyl acetate with a volume ratio of 30:1, to give III-i white solid (0.0581g, 58% yield).
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