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[ CAS No. 151169-67-4 ] {[proInfo.proName]}

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Chemical Structure| 151169-67-4
Chemical Structure| 151169-67-4
Structure of 151169-67-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 151169-67-4 ]

CAS No. :151169-67-4 MDL No. :MFCD02258950
Formula : C6H5BClNO4 Boiling Point : -
Linear Structure Formula :- InChI Key :LQCCRPUZTXKDGB-UHFFFAOYSA-N
M.W : 201.37 Pubchem ID :5006651
Synonyms :

Calculated chemistry of [ 151169-67-4 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 50.1
TPSA : 86.28 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.62 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.28
Log Po/w (WLOGP) : -0.07
Log Po/w (MLOGP) : -0.22
Log Po/w (SILICOS-IT) : -2.16
Consensus Log Po/w : -0.23

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.1
Solubility : 1.58 mg/ml ; 0.00786 mol/l
Class : Soluble
Log S (Ali) : -2.69
Solubility : 0.41 mg/ml ; 0.00204 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.29
Solubility : 10.3 mg/ml ; 0.0513 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.16

Safety of [ 151169-67-4 ]

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

Application In Synthesis of [ 151169-67-4 ]

* 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 [ 151169-67-4 ]

[ 151169-67-4 ] Synthesis Path-Downstream   1~43

  • 1
  • [ CAS Unavailable ]
  • [ 151169-67-4 ]
  • [ 916050-62-9 ]
YieldReaction ConditionsOperation in experiment
57% With nitrogen In hexane; water; ethyl acetate; N,N-dimethyl-formamide EXAMPLES Synthesis of 2-(4-chloro-3-nitrophenyl)pyridine 2: To a three-necked flask equipped with a magnetic stir bar and a condenser, added 4-chloro-3-nitrophenylboronic acid (3968 mg, 19.7 mmol) and NaHCO3 (3310 mg, 39.4 mmol). The flask was sealed and then evacuated and backfilled with nitrogen. Repeated the evacuation and backfill procedure four additional times. After that solvents DMF (40 mL) and H2O (20 mL) were added independently by syringe. The mixture was bubbled with nitrogen through a needle for 30 minutes. Then 2-bromopyridine (3.11 mL, 21.7 mmol) and Pd(PPh3)4 (1138 mg, 0.99 mmol) were added under the atmosphere of nitrogen. The mixture was heated to reflux (about 95-105° C.) in an oil bath. The reaction was monitored by TLC and after about 4.5 hours the reaction was completed. Then cooled down to ambient temperature and water was added. Then the mixture was filtered and washed with ethyl acetate. The organic layer of the filtrate was separated and the aqueous layer was extracted with ethyl acetate for twice. The combined organic layer was dried over sodium sulfate. Then filtered and washed with ethyl acetate. The filtrate was concentrated under reduced pressure using a rotary evaporator and the residue was purified through column chromatography on silica gel using hexane and ethyl acetate (20:1-15:1-10:1-5:1) as eluent to afford the desired product 2-(4-chloro-3-nitrophenyl)pyridine 2 as a grey solid 2.65 g in 57% yield. 1H NMR (DMSO-d6, 400 MHz): δ 7.47-7.50 (m, 1H), 7.92 (d, J=8.4 Hz, 1H), 7.99 (td, J=7.6, 0.8 Hz, 1H), 8.16 (d, J=8.0 Hz, 1H), 8.44 (dd, J=8.0, 0.8 Hz, 1H), 8.74-8.75 (m, 1H), 8.77 (d, J=2.0 Hz, 1H).
50% With sodium carbonate In water; N,N-dimethyl-formamide at 100℃; for 2h; 2.a A mixture of4-chloro-3-nitrophenylboronic acid (500mg, 2.58 mmoles), 2-bromopyridine (380 mg, 2.58 mmoles), tetrakistriphenylphosphine palladium(O) (100 mg, 0.086 mmoles), sodium carbonate (800 mg, 7.5 mmoles) in dimethylformamide (15 mL) and water (2.5 mL) was heated at 1000C for 2 hours. The mixture was diluted with water and extracted into ethyl acetate (x2). The combined extracts were washed with water and brine, dried and evaporated. Flash chromatography (fine silica, dichloromethane) afforded the title EPO compound (300 mg, 50%). 1 H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.36 (ddd, J=7.39, 4.86, 1.14 Hz, 1 H) 7.67 (d, J=8.34 Hz, 1 H) 7.78 - 7.89 (m, 2 H) 8.21 (dd, J=8.34, 2.02 Hz, 1 H) 8.58 (d, J=2.02 Hz, 1 H) 8.75 (d, J=4.80 Hz, 1 H)
50% With sodium carbonate In water; N,N-dimethyl-formamide at 100℃; for 2h; 2.a A mixture of 4-chloro-3- nitrophenylboronic acid (500mg, 2.58 mmoles), 2-bromopyridine (380 mg, 2.58 mmoles), tetrakistriphenylphosphine palladium(O) (100 mg, 0.086 mmoles), sodium carbonate (800 mg, 7.5 mmoles) in dimethylformamide (15 ml.) and water (2.5 ml.) was heated at 1000C for 2 hours. The mixture was diluted with water and extracted into ethyl acetate (x2). The combined extracts were washed with water and brine, dried and evaporated. Flash chromatography (fine silica, dichloromethane) afforded the title compound (300 mg, 50%). 1 H NMR (400 MHz, CHLOROFORM- cQ δ ppm 7.36 (ddd, J=7.39, 4.86, 1.14 Hz, 1 H) 7.67 (d, J=8.34 Hz, 1 H) 7.78 - 7.89 (m, 2 H) 8.21 (dd, J=8.34, 2.02 Hz, 1 H) 8.58 (d, J=2.02 Hz, 1 H) 8.75 (d, J=4.80 Hz, 1 H)
  • 2
  • (4-chloro-3-nitrophenyl)boronic acid [ No CAS ]
  • [ 4595-60-2 ]
  • [ 1173824-98-0 ]
YieldReaction ConditionsOperation in experiment
64% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; at 100℃; for 1h; A mixture of 4-chloro-3-nitrophenylboronic acid (520 mg, 2.58 mmoles), <strong>[4595-60-2]2-<strong>[4595-60-2]bromopyrimidine</strong></strong> (410 mg, 2.58 mmoles), tetrakis(triphenylphosphine)palladium(0) (100 mg, 0.08 mmoles) and sodium carbonate (800 mg, 7.5 mmoles) in water (2.5 ml_) and dimethylformamide (15 ml_) was heated at 1000C for 1hour. Water was added and the mixture extracted with ethyl acetate (x2). The combined extracts were dried and evaporated then chromatographed (dichloromethane-methanol) to give the title compound (390 mg, 64%). 1 H NMR (400 MHz, CHLOROFORM-d) delta ppm 7.32 (t, J=4.93 Hz, 1 H) 7.69 (d, J=8.59 Hz, 1 H) 8.64 (dd, J=8.34, 2.02 Hz,1 H) 8.87 (d, J=5.05 Hz, 2 H) 9.02 (d, J=2.02 Hz, 1 H).
  • 3
  • [ 151169-67-4 ]
  • [ 817618-19-2 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
68% With sodium carbonate In water; N,N-dimethyl-formamide at 150℃; for 0.333333h; Microwave heating; 116.b A mixture of 4-chloro-3-nitrophenylboronic acid (245 mg, 1.225 mmoles), 1 ,1 -dimethylethyl (6-bromo-2-pyridinyl)methylcarbamate (350 mg, 1.225 mmoles), sodium carbonate (400 mg, 3.68 mmoles) and tetrakis(triphenylphosphine)palladium(0) (50 mg, 0.04 mmoles) in 3:1 dimethylformamide-water (5 ml_) was sealed in a pressure tube and heated at 1500C for 20 minutes in a microwave reactor. The mixture was diluted with water and extracted with ethyl acetate (x2). Combined extracts were washed with brine, dried and evaporated. Flash chromatography (0-20% ethyl acetate-hexane) gave the title compound (300 mg, 68%). 1 H NMR (400 MHz, CHLOROFORM-o) δ ppm 1.57 (s, 9 H) 3.51 (s, 3 H) 7.47 (dd, J=7.58, 0.76 Hz, 1 H) 7.63 (d, J=8.59 Hz, 1 H) 7.72 - 7.78 (m, 1 H) 7.79 - 7.84 (m, 1 H) 8.17 (dd, J=8.46, 2.15 Hz, 1 H) 8.54 (d, J=2.02 Hz, 1 H).
  • 4
  • [ 151169-67-4 ]
  • [ CAS Unavailable ]
  • [ 916052-30-7 ]
YieldReaction ConditionsOperation in experiment
44.5% With sodium carbonate In water; N,N-dimethyl-formamide at 150℃; for 0.166667h; Microwave heating; 106.a A mixture of4-chloro-3-nitrophenylboronic acid (427 mg, 2.13 mmoles), 3-iodoanisole (500 mg, 2.13 mmoles), sodium carbonate (600 mg, 5.66 mmoles) and tetrakis(triphenylphosphine)palladium(0) (50 mg, 0.04 mmoles) in 3:1 dimethylformamide-water (5 mL) was sealed in a pressure tube and heated at 15O0C for 10 minutes in a microwave reactor. The mixture was diluted with water and extracted with ethyl acetate (x2). Combined extracts were washed with brine, dried and evaporated. Flash chromatography (0-30% ethyl acetate-hexane) gave the title compound (250 mg, 44.5%). 1 H NMR (400 MHz,CHLOROFORM-Gf) δ ppm 3.89 (s, 3 H) 6.98 (ddd, J=8.34, 2.53, 0.76 Hz, 1 H) 7.06 - 7.12 (m, 1 H) 7.16 (ddd, J=7.71 , 1.64, 0.76 Hz, 1 H) 7.41 (t, J=7.96 Hz, 1 H) 7.61 (d, J=8.59 Hz, 1 H) 7.73 (dd, J=8.34, 2.27 Hz, 1 H) 8.08 (d, J=2.02 Hz, 1 H)
  • 5
  • [ 1445-39-2 ]
  • (4-chloro-3-nitrophenyl)boronic acid [ No CAS ]
  • [ 742700-78-3 ]
YieldReaction ConditionsOperation in experiment
70% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; at 150℃; for 0.166667h;Microwave heating; A mixture of 4-chloro-3-nitrophenylboronic acid (600 mg, 3.0 mmoles), <strong>[1445-39-2]2-amino-5-iodopyrimidine</strong> (680 mg, 3.0 mmoles), sodium carbonate (900 mg, 8.5 mmoles) and tetrakis(triphenylphosphine)palladium(0) (80 mg, 0.07 mmoles) in 3:1 dimethylformamide-water (10 ml_) was sealed in a pressure tube and heated at 1500C for 10 minutes in a microwave reactor. The mixture was diluted with water and extracted with ethyl acetate (x2). Combined extracts were washed with brine, dried and evaporated. Flash chromatography (0-5% methanol-dichloromethane) gave the title compound (525 mg, 70%). 1 H NMR(400 MHz, DMSO-alphafe) delta ppm 7.04 (s, 2 H) 7.81 (d, J=8.59 Hz, 1 H) 8.00 (dd, J=8.59, 2.27 Hz, 1 H) 8.36 (d, J=2.27 Hz, 1 H) 8.70 (s, 2 H).
  • 6
  • [ 151169-67-4 ]
  • [ CAS Unavailable ]
  • [ 1229698-97-8 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate In water; N,N-dimethyl-formamide at 100℃; for 0.5h; Inert atmosphere; Microwave irradiation; 4.A Example 4A 4,4"-Dichloro-3,3"-dinitro-[1,1'; 4',1"]terphenyl 1,4-diiodobenzene (200 mg, 0.606 mmol), 4-chloro-3-nitrophenylboronic acid (256 mg, 1.273 mmol), and Pd(PPh3)4 (35 mg, 0.03 mmol), were added to a flask followed by Na2CO3 (321 mg, 3.03 mmol). DMF (6.0 mL) and water (1.0 mL) were added and the mixture was bubbled with N2 for ten minutes. Heated solution to 110° C. for 30 min in a microwave reactor. A large amount of precipitate formed. Water and dichloromethane were added and the mixture was extracted with dichloromethane. Dried over MgSO4, filtered and concentrated to give the title compound as a light brown solid. (250 mg), which was used without further purification.
  • 7
  • [ 151169-67-4 ]
  • [ 1423134-92-2 ]
  • [ 1423134-43-3 ]
YieldReaction ConditionsOperation in experiment
47% With potassium fluoride; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 100℃; for 60h; 32 Tert-butyl 4-{3-[(3R)-3-({1-[5-(4-chloro-3-nitrophenyl)pyridin-3-yl]-3-methoxy-3-oxopropyl}carbamoyl)piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate To 171.5 mg (0.28 mmol) tert-butyl 4-{3-[(3R)-3-[1-(5-bromopyridin-3-yl)-3-methoxy-3-oxopropyl]carbamoyl}piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate (example 8c) in 7 ml toluene were added 6.5 mg (0.01 mmol) tetrakis(triphenylphosphine)palladium(0), 68.0 mg (0.34 mmol) (4-chloro-3-nitrophenyl)boronic acid in 1.7 ml ethanol and 50.7 mg (0.87 mmol) potassium fluoride in 1.7 ml water. The mixture was stirred at 100 °C for 60 hours, diluted with water and extracted with ethyl acetate. The organic phase was dried over sodium sulfate and concentrated in vacuum. Chromatography over 10 g silica gel (dichloromethane / ethanol 100/0-95/5-90/10) gave 100 mg (47 %) ferf-butyl 4-{3-[(3R)-3-({1-[5-(4-chloro-3-nitrophenyl)pyridin-3-yl]-3-methoxy-3-oxopropyl}carbamoyl)piperidin-1-yl]-3-oxopropyl} piperidine-1-carboxylate. UPLC (ACN-HCOOH): Rt. = 1.30 min MS (ES + ): m/e = 686.2 (M + H + )
  • 8
  • [ 1193-21-1 ]
  • [ 151169-67-4 ]
  • [ 954218-61-2 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane at 90℃; for 3.75h; Inert atmosphere; 2.1 to a degassed stirred solution of 4-chloro-3-nitro-benzene boronic acid (leq) and 4,6-dichloropyrimidine (1.44eq) in 1,4- dioxane (16vol) and 2N K2C03 (8vol) was added Pd(PPh3)4 (0.06eq) and the mixture heated to 90°C for 3.75 hours under an atmosphere of nitrogen gas. The cooled reaction mixture had the solvents removed under reduced pressure. DCM (25vol) and water (25vol) were then added and the undissolved material removed by filtration through celite. The organic phase from the filtrate was concentrated under reduced pressure whilst adsorbing on to silica gel (8.2g). The residue was purified using dry flash chromatography (gradient up to 10% EtOAc: heptane) to afford the target compound.
  • 9
  • [ 151169-67-4 ]
  • [ 1426319-62-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,4-dioxane / 3.75 h / 90 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); triethylamine / 18 h / 50 °C / 3750.38 Torr / Inert atmosphere 3: hydrogenchloride; water / tert-butyl methyl ether
  • 10
  • [ 151169-67-4 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,4-dioxane / 3.75 h / 90 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); triethylamine / 18 h / 50 °C / 3750.38 Torr / Inert atmosphere
  • 11
  • [ 151169-67-4 ]
  • [ 916050-63-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: nitrogen / water; hexane; ethyl acetate; N,N-dimethyl-formamide 2: ethanol; hexane; ethyl acetate
Multi-step reaction with 2 steps 1.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / water; N,N-dimethyl-formamide / 2 h / 100 °C 2.1: ethanol; tin(ll) chloride / 2 h / 60 °C 2.2: Alkaline conditions
Multi-step reaction with 2 steps 1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / water; N,N-dimethyl-formamide / 2 h / 100 °C 2: tin(ll) chloride / ethanol / 2 h / 60 °C
  • 12
  • [ 151169-67-4 ]
  • [ 1585211-09-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: nitrogen / water; hexane; ethyl acetate; N,N-dimethyl-formamide 2: ethanol; hexane; ethyl acetate 3: tris-(dibenzylideneacetone)dipalladium(0) / hexane; ethyl acetate; 1,4-dioxane
  • 13
  • [ 189330-06-1 ]
  • [ 151169-67-4 ]
  • [ 1614825-47-6 ]
YieldReaction ConditionsOperation in experiment
57% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxane; water at 95℃; for 1.5h; Inert atmosphere; 4 (Reference Example 4) 2-(4-Chloro-3-nitrophenyl)thiophene-3-carboxamide A solution of 493 mg (2.39 mmol) of 2-bromothiophene-3-carboxamide (synthesized according to WO 10/036497) and 645 mg (3.20 mmol) of 4-chloro-3-nitrophenyl boronic acid in 1,4-dioxane (7 ml) was degassed, a suspension of 1.26 g (11.9 mmol) of sodium carbonate in 2 ml of water was added, then 0.196 g (0.240 mmol) of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride methylene chloride adduct was added, and the mixture was heated and stirred under an argon atmosphere at 95°C for 1.5 hours. After completion of the reaction, the reaction mixture was allowed to cool, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, subsequently dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (elution solvent; hexane:ethyl acetate = 63:37 to 42:58 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 382 mg (1.35 mmol, yield 57%) of the title compound as a white solid. Mass spectrum (CI, m/z): 283 [M+1]+. 1H-NMR spectrum (400 MHz, CD2Cl2) δ : 8.08 (1H, d, J = 2.1 Hz), 7.73 (1H, dd, J = 8.3, 2.2 Hz), 7.61 (1H, d, J = 8.4 Hz), 7.43 (1H, d, J = 5.3 Hz), 7.34 (1H, d, J = 5.3 Hz), 5.63 (2H, brs).
  • 14
  • [ 151169-67-4 ]
  • [ 1614824-67-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 1.5 h / 95 °C / Inert atmosphere 2: sodium carbonate; palladium diacetate; tricyclohexylphosphine / 1,4-dioxane; water / 2 h / 95 °C / Inert atmosphere 3: N-chloro-succinimide / N,N-dimethyl-formamide / 2.33 h / 80 °C / Inert atmosphere 4: pyridine; bis-[(trifluoroacetoxy)iodo]benzene / toluene / 2 h / 80 °C / Inert atmosphere
  • 15
  • [ 151169-67-4 ]
  • [ 1614825-65-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 1.5 h / 95 °C / Inert atmosphere 2: sodium carbonate; palladium diacetate; tricyclohexylphosphine / 1,4-dioxane; water / 2 h / 95 °C / Inert atmosphere 3: N-chloro-succinimide / N,N-dimethyl-formamide / 2.33 h / 80 °C / Inert atmosphere
  • 16
  • [ 151169-67-4 ]
  • [ 1614824-68-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 1.5 h / 95 °C / Inert atmosphere 2: sodium carbonate; palladium diacetate; tricyclohexylphosphine / 1,4-dioxane; water / 2 h / 95 °C / Inert atmosphere 3: N-chloro-succinimide / N,N-dimethyl-formamide / 2.33 h / 80 °C / Inert atmosphere 4: pyridine; bis-[(trifluoroacetoxy)iodo]benzene / toluene / 2 h / 80 °C / Inert atmosphere 5: water; sodium hydroxide / isopropyl alcohol / 93 h / 20 °C
  • 17
  • [ 151169-67-4 ]
  • [ 1614824-69-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 1.5 h / 95 °C / Inert atmosphere 2: sodium carbonate; palladium diacetate; tricyclohexylphosphine / 1,4-dioxane; water / 2 h / 95 °C / Inert atmosphere 3: N-chloro-succinimide / N,N-dimethyl-formamide / 2.33 h / 80 °C / Inert atmosphere 4: pyridine; bis-[(trifluoroacetoxy)iodo]benzene / toluene / 3.5 h / 80 °C / Inert atmosphere
  • 18
  • [ 151169-67-4 ]
  • [ 1614824-70-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 1.5 h / 95 °C / Inert atmosphere 2: sodium carbonate; palladium diacetate; tricyclohexylphosphine / 1,4-dioxane; water / 2 h / 95 °C / Inert atmosphere 3: N-chloro-succinimide / N,N-dimethyl-formamide / 2.33 h / 80 °C / Inert atmosphere 4: pyridine; bis-[(trifluoroacetoxy)iodo]benzene / toluene / 3.5 h / 80 °C / Inert atmosphere 5: water; sodium hydroxide / isopropyl alcohol / 94 h / 20 °C
  • 19
  • [ 151169-67-4 ]
  • [ 1614824-72-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 1.5 h / 95 °C / Inert atmosphere 2: sodium carbonate; palladium diacetate; tricyclohexylphosphine / 1,4-dioxane; water / 2 h / 95 °C / Inert atmosphere 3: N-chloro-succinimide / N,N-dimethyl-formamide / 2.33 h / 80 °C / Inert atmosphere 4: pyridine; bis-[(trifluoroacetoxy)iodo]benzene / toluene / 2 h / 80 °C / Inert atmosphere 5: water; sodium hydroxide / isopropyl alcohol / 95 h / 20 °C
  • 20
  • [ 151169-67-4 ]
  • [ 1614825-59-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 1.5 h / 95 °C / Inert atmosphere 2: sodium carbonate; palladium diacetate; tricyclohexylphosphine / 1,4-dioxane; water / 2 h / 95 °C / Inert atmosphere
  • 21
  • [ 151169-67-4 ]
  • [ 1614824-71-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 1.5 h / 95 °C / Inert atmosphere 2: sodium carbonate; palladium diacetate; tricyclohexylphosphine / 1,4-dioxane; water / 2 h / 95 °C / Inert atmosphere 3: N-chloro-succinimide / N,N-dimethyl-formamide / 2.33 h / 80 °C / Inert atmosphere 4: pyridine; bis-[(trifluoroacetoxy)iodo]benzene / toluene / 2 h / 80 °C / Inert atmosphere
  • 22
  • [ 151169-67-4 ]
  • [ 1771743-32-8 ]
  • [ 2007950-47-0 ]
YieldReaction ConditionsOperation in experiment
0.86 g With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 100℃; 4.3 Step 3 1 g (2.14 mmol) of 1-[2,6-dimethyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-4-iodopyrazoleand 0.675 g (3 mmol) of 3-nitro-4-chlorophenylboronic acid were initially charged in 18 ml of 1,4-dioxane, and 0.16 g (0.21 mmol) of 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) chloride and 9.6 ml of a 2M aqueous Na2CO3 solution were added. The mixture was stirred at 100° C. until conversion was complete. After the reaction mixture had cooled down, the complete mixture was concentrated on silica gel on a rotary evaporator and then chromatographed using silica gel (cyclohexane/ethyl acetate gradient). 0.86 g (78.1% of theory) were obtained as a colourless solid. 1H-NMR, 400 MHz, d6-DMSO, δ 8.71 (s, 1H), 8.44 (s, 1H), 8.39 (s, 1H), 8.02 (d, 1H), 7.82 (d, 1H), 7.60 (s, 2H), 2.13 (s, 6H). lgP=5.39; MH+=496.0
  • 23
  • [ 151169-67-4 ]
  • [ 916051-91-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / water; N,N-dimethyl-formamide / 1 h / 100 °C 2.1: ethanol; tin(ll) chloride / 2 h / Heating / reflux 2.2: Alkaline conditions
  • 24
  • [ 151169-67-4 ]
  • [ 916052-31-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / water; N,N-dimethyl-formamide / 0.17 h / 150 °C / Microwave heating 2.1: ethanol; tin(ll) chloride / 2 h / Heating / reflux 2.2: Alkaline conditions
  • 25
  • [ 151169-67-4 ]
  • [ 916052-22-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / water; N,N-dimethyl-formamide / 0.17 h / 150 °C / Microwave heating 2.1: ethanol; tin(ll) chloride / 2 h / Heating / reflux 2.2: Acidic conditions
  • 26
  • [ 151169-67-4 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / water; N,N-dimethyl-formamide / 0.33 h / 150 °C / Microwave heating 2: acetic acid; zinc / 1.5 h
  • 27
  • [ 151169-67-4 ]
  • [ 916050-61-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / water; N,N-dimethyl-formamide / 2 h / 100 °C 2.1: ethanol; tin(ll) chloride / 2 h / 60 °C 2.2: Alkaline conditions 3.1: 1,4-dioxane / 2 h / 160 °C
Multi-step reaction with 3 steps 1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / water; N,N-dimethyl-formamide / 2 h / 100 °C 2: tin(ll) chloride / ethanol / 2 h / 60 °C 3: N,N-dimethyl-formamide / 2 h / 160 °C
  • 28
  • [ 151169-67-4 ]
  • [ 916051-90-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / water; N,N-dimethyl-formamide / 1 h / 100 °C 2.1: ethanol; tin(ll) chloride / 2 h / Heating / reflux 2.2: Alkaline conditions 3.1: N,N-dimethyl-formamide / 2 h / 180 °C
  • 29
  • [ 151169-67-4 ]
  • [ 916052-29-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / water; N,N-dimethyl-formamide / 0.17 h / 150 °C / Microwave heating 2.1: ethanol; tin(ll) chloride / 2 h / Heating / reflux 2.2: Alkaline conditions 3.1: valeric acid / 0.67 h / 180 °C
  • 30
  • [ 151169-67-4 ]
  • [ 916052-47-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / water; N,N-dimethyl-formamide / 0.33 h / 150 °C / Microwave heating 2: acetic acid; zinc / 1.5 h 3: valeric acid / 0.17 h / 180 °C
  • 31
  • [ 151169-67-4 ]
  • [ 916052-20-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / water; N,N-dimethyl-formamide / 0.17 h / 150 °C / Microwave heating 2.1: ethanol; tin(ll) chloride / 2 h / Heating / reflux 2.2: Acidic conditions 3.1: valeric acid / 0.33 h / 180 °C
  • 32
  • [ 151169-67-4 ]
  • [ 2279110-19-7 ]
  • [ 2279110-59-5 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; water; toluene at 100℃; Inert atmosphere; Experimental Procedure for the Preparation 1-(5-fluoro-2, 6-diphenylpyrimidin-4-yl)ethanone (12a): General procedure: Compound 10a (1.3 g, 5.20 mmol), compound 11a (0.70 g, 5.72 mmol) and Na2CO3 (2.20 g,20.80 mmol), were taken in Toluene: THF: Water (10:5:5 ml) under N2 atm, was addedPd(PPh3)4 (0.60 g, 0.52 mmol) and the reaction mixture was stirred at 95 0C for 6 h. Theprogress of the reaction was monitored by TLC (2 % ethyl acetate in petroleum ether) showedcompletion of the reaction. After completion of the reaction; water was added to the reactionmixture and extracted with ethyl acetate. Combined organic layers were washed with water,brine and dried over Na2SO4 and evaporated the solvents to afford the crude compound.Thecrude compound was purified by silica gel column chromatography, eluted the with 5% ethylacetate in petroleum ether to give the pure compound 12a (1.2 g; 4.10 mmol, 79%) as whitesolid.
  • 33
  • [ 151169-67-4 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; tetrahydrofuran; water / 100 °C / Inert atmosphere 2: hydroxylamine hydrochloride; sodium hydroxide / methanol / 16 h / 20 °C / Inert atmosphere
  • 34
  • [ 151169-67-4 ]
  • [ 2279111-19-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; tetrahydrofuran; water / 100 °C / Inert atmosphere 2: hydroxylamine hydrochloride; sodium hydroxide / methanol / 16 h / 20 °C / Inert atmosphere 3: sodium hydroxide / N,N-dimethyl-formamide / 6 h / 0 - 20 °C / Inert atmosphere
  • 35
  • [ 151169-67-4 ]
  • [ 1175653-38-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 12 h / Reflux; Inert atmosphere 2: palladium on activated charcoal; hydrogen / methanol / 4 h / 20 °C
  • 36
  • [ 151169-67-4 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 12 h / Reflux; Inert atmosphere 2.1: palladium on activated charcoal; hydrogen / methanol / 4 h / 20 °C 3.1: sodium nitrite; hydrogenchloride / tetrahydrofuran; water / 0.33 h / 0 °C / Cooling with ice 3.2: 1.17 h / 0 - 20 °C / Cooling with ice
  • 37
  • [ 151169-67-4 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 12 h / Reflux; Inert atmosphere 2.1: palladium on activated charcoal; hydrogen / methanol / 4 h / 20 °C 3.1: sodium nitrite; hydrogenchloride / tetrahydrofuran; water / 0.33 h / 0 °C / Cooling with ice 3.2: 1.17 h / 0 - 20 °C / Cooling with ice 4.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; 1,2-dimethoxyethane / 12 h / Inert atmosphere; Reflux
  • 38
  • [ 151169-67-4 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 12 h / Reflux; Inert atmosphere 2.1: palladium on activated charcoal; hydrogen / methanol / 4 h / 20 °C 3.1: sodium nitrite; hydrogenchloride / tetrahydrofuran; water / 0.33 h / 0 °C / Cooling with ice 3.2: 1.17 h / 0 - 20 °C / Cooling with ice 4.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; 1,2-dimethoxyethane / 12 h / Inert atmosphere; Reflux 5.1: sodium nitrite; hydrogenchloride / tetrahydrofuran; water / 0.33 h / 0 °C / Cooling with ice 5.2: 1.17 h / 0 - 20 °C / Cooling with ice
  • 39
  • [ 151169-67-4 ]
  • [ 2618368-52-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 12 h / Reflux; Inert atmosphere 2.1: palladium on activated charcoal; hydrogen / methanol / 4 h / 20 °C 3.1: sodium nitrite; hydrogenchloride / tetrahydrofuran; water / 0.33 h / 0 °C / Cooling with ice 3.2: 1.17 h / 0 - 20 °C / Cooling with ice 4.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; 1,2-dimethoxyethane / 12 h / Inert atmosphere; Reflux 5.1: sodium nitrite; hydrogenchloride / tetrahydrofuran; water / 0.33 h / 0 °C / Cooling with ice 5.2: 1.17 h / 0 - 20 °C / Cooling with ice 6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1.5 h / 0 - 20 °C
  • 40
  • [ 151169-67-4 ]
  • [ 2618368-17-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 12 h / Reflux; Inert atmosphere 2.1: palladium on activated charcoal; hydrogen / methanol / 4 h / 20 °C 3.1: sodium nitrite; hydrogenchloride / tetrahydrofuran; water / 0.33 h / 0 °C / Cooling with ice 3.2: 1.17 h / 0 - 20 °C / Cooling with ice 4.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; 1,2-dimethoxyethane / 12 h / Inert atmosphere; Reflux 5.1: sodium nitrite; hydrogenchloride / tetrahydrofuran; water / 0.33 h / 0 °C / Cooling with ice 5.2: 1.17 h / 0 - 20 °C / Cooling with ice 6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1.5 h / 0 - 20 °C 7.1: sodium carbonate; <i>tert</i>-butylamine / ethyl acetate / 24 h / 100 °C / Sealed tube; Inert atmosphere; Green chemistry
  • 41
  • [ 151169-67-4 ]
  • [ 100-39-0 ]
  • [ 53271-21-9 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran for 12h; Reflux; Inert atmosphere;
  • 42
  • [ 151169-67-4 ]
  • [ CAS Unavailable ]
  • [ 2408199-09-5 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; toluene for 4h; Inert atmosphere; Reflux; 2.c Step c: General procedure: A mixture of N-((2-bromopyrimidin-5-yl)methyl)-2-chloro-6- (0115) (trifluoromethyl)pyridin-4-amine (1.0 Eq.), the corresponding boronic acid (1.16 Eq.), sodium carbonate (2 M, 33 mL/mmol) and tetrakis(triphenylphosphine) palladium (2 mol%) were suspended in an oxygen-free toluene/ethanol (1 :1, v:v, 250 mL/mmol) solution and refluxed for 4 h under nitrogen atmosphere. The reaction mixture was cooled to room temperature, and excess solvent was removed under reduced pressure. The aqueous layer was extracted with ethyl acetate. The organic layer was washed once with saturate NaCl solution and once with water, dried over MgSO4, filtered and the solution was concentrated under reduced pressure. The residue was purified by prep-HPLC using acetonitrile and water as eluent to afford the desired compound.
  • 43
  • [ 151169-67-4 ]
  • [ 2553263-27-5 ]
YieldReaction ConditionsOperation in experiment
59 Example 59 Example 59 4-(4-Chloro-3-nitrophenyl)-2-(4-fluorophenyl)phthalazin-1(2H)-one Compound I-2 (100 mg, 0.36 mmol) and 4-chloro-3-nitrophenylboronic acid (86 mg, 0.43 mmol) were reacted in the same manner as in Step 1 of Example 1, to obtain 125 mg of the title compound. LC-MS (ESI, m/z) = 396.0 (M+H+)
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