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[ CAS No. 147102-97-4 ] {[proInfo.proName]}

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Chemical Structure| 147102-97-4
Chemical Structure| 147102-97-4
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Product Details of [ 147102-97-4 ]

CAS No. :147102-97-4 MDL No. :MFCD18411295
Formula : C10H8BClO2 Boiling Point : -
Linear Structure Formula :- InChI Key :PIHWNQAUHGAUGC-UHFFFAOYSA-N
M.W : 206.43 Pubchem ID :45116892
Synonyms :

Calculated chemistry of [ 147102-97-4 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 58.78
TPSA : 40.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.64 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.7
Log Po/w (WLOGP) : 1.17
Log Po/w (MLOGP) : 1.91
Log Po/w (SILICOS-IT) : 0.96
Consensus Log Po/w : 1.35

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.28
Solubility : 0.107 mg/ml ; 0.000521 mol/l
Class : Soluble
Log S (Ali) : -3.2
Solubility : 0.129 mg/ml ; 0.000627 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.59
Solubility : 0.0536 mg/ml ; 0.000259 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.9

Safety of [ 147102-97-4 ]

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 [ 147102-97-4 ]

* 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 [ 147102-97-4 ]

[ 147102-97-4 ] Synthesis Path-Downstream   1~52

  • 1
  • [ 147102-97-4 ]
  • C41H27N [ No CAS ]
  • 2
  • [ 147102-97-4 ]
  • C47H31N [ No CAS ]
  • 3
  • [ 147102-97-4 ]
  • C29H21ClO [ No CAS ]
  • 4
  • [ 147102-97-4 ]
  • C29H19Cl [ No CAS ]
  • 5
  • [ 147102-97-4 ]
  • [ 13047-06-8 ]
  • C23H15ClO [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; The compound A (35.0 g, 168.6 mmol) and B (40.0 g, 153.3 mmol) were completely dissolved in 300 ml of tetrahydrofuran and then 3M aqueous potassium carbonate solution (150 ml) was added thereto to obtain tetrakis triphenylphosphinopalladium 1.8 g, 1.53 mmol), and the mixture was heated with stirring for 8 hours. After the temperature was lowered to room temperature and the reaction was terminated, the organic layer was separated and treated with magnesium sulfate. After filtration and concentration, the compound of formula (C) (45.0 g, yield 86%) was prepared and used in the next reaction without further purification
  • 6
  • [ 147102-97-4 ]
  • C35H22 [ No CAS ]
  • 7
  • [ 147102-97-4 ]
  • C41H25N [ No CAS ]
  • 8
  • [ 147102-97-4 ]
  • C44H27N3 [ No CAS ]
  • 9
  • [ 147102-97-4 ]
  • C29H19ClO [ No CAS ]
  • 10
  • [ 147102-97-4 ]
  • C29H17Cl [ No CAS ]
  • 11
  • [ 147102-97-4 ]
  • [ 36804-63-4 ]
  • C23H13ClO [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 8.0h;Reflux; The above compound A (30.0 g, 146 mmol) and B (34.4 g, 133 mmol)After completely dissolved in tetrahydrofuran (300 ml)3M aqueous potassium carbonate solution (150 ml) was added,Tetraquistriphenylphosphino palladium (1.5 g, 1.33 mmol) was added thereto,And the mixture was heated with stirring for 8 hours.After the temperature was lowered to room temperature and the reaction was terminated, the organic layer was separated and treated with magnesium sulfate.After filtration and concentration, Compound C (39.8 g, yield 88%) was prepared.
  • 12
  • [ 147102-97-4 ]
  • [ 41513-04-6 ]
  • C16H9Cl2NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 24.0h;Reflux; (4-chloronaphthalen-1-yl) boronic acid (30 g, 145.6 mmol)And 1-bromo-4-chloro-2-nitrobenzene (33.5 g, 142.7 mmol) were placed in a 500 ml round bottom flask and dissolved in 200 ml THF. Potassium carbonate (60.4 g, 436.8 mmol) dissolved in 100 ml water is added and stirred to raise the temperature. When refluxing starts, tetrakis (triphenylphosphine) palladium (5.0 g, 4.37 mmol) is added in a batch and reacted for 24 hours. When the reaction is completed, the reaction mixture is cooled to separate the water and the organic layer. Only the organic layer is collected, dried over anhydrous magnesium sulfate, and filtered through celite. This was concentrated under reduced pressure to obtain a column. After drying, 37.4 g (yield 81%) of A-1 was prepared.
  • 13
  • [ 147102-97-4 ]
  • C22H13Cl2N [ No CAS ]
  • 14
  • [ 147102-97-4 ]
  • C66H53N3O2 [ No CAS ]
  • 15
  • [ 147102-97-4 ]
  • C72H61N3O2 [ No CAS ]
  • 16
  • [ 147102-97-4 ]
  • C52H47F2N3Si2 [ No CAS ]
  • 17
  • [ 147102-97-4 ]
  • C68H57N3S2 [ No CAS ]
  • 18
  • [ 147102-97-4 ]
  • C28H17Cl2N [ No CAS ]
  • 19
  • [ 147102-97-4 ]
  • C16H9Cl2N [ No CAS ]
  • 20
  • [ 147102-97-4 ]
  • [ 23449-08-3 ]
  • C31H20ClN3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 12.0h;Reflux; Inert atmosphere; Reagent 1 (100.0 g, 257.55 mmol) and Reagent 2 (58.5 g, 206.43 mmol) were put into 1,000 ml of tetrahydrofuran under a nitrogen atmosphere, and the resulting mixture was stirred and refluxed. Thereafter, potassium carbonate (71.2 g, 515.11 mmol) was dissolved in 200 ml of water, the resulting solution was introduced into the mixture, the resulting mixture was sufficiently stirred, and then tetrakistriphenyl-phosphinopalladium (8.9 g, 7.73 mmol) was introduced thereinto. After the reaction for 12 hours, the temperature of the product was lowered to normal temperature and a produced solid was filtered. After the filtration, the solid was washed with 100 ml of tetrahydrofuran, 500 ml of ethyl acetate, 500 ml of water, and 300 ml of ethanol. The resulting product was dried to prepare Compound 1A (112.6 g, 88%). Reagents 1 and 2 were purchased from Aldrich and TCI, respectively.
81% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 8.0h;Inert atmosphere; Reflux; In a nitrogen atmosphere2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (reagent 1-1, 50 g, 129 mmol)(4-chloronaphthalen-1-yl) boronic acid (reagent 1-2, 29.2 g, 142 mmol)Were added to 600 ml of tetrahydrofuran and stirred and refluxed.After this, potassium carbonate (53 g, 386 mmol)Was dissolved in 60 ml of water, and the mixture was sufficiently stirred. Then, tetrakistriphenylphosphinopalladium (4.5 g, 4 mmol) was added thereto.After 8 hours of reaction, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and then the organic layer was dried with magnesium sulfate.The organic layer was then distilled under reduced pressure and recrystallized using ethyl acetate.The resulting solid was filtered and dried to give Intermediate 1-1 (49 g, 81%).
  • 21
  • [ 147102-97-4 ]
  • C43H27N3S [ No CAS ]
  • 22
  • [ 147102-97-4 ]
  • C43H27N3O [ No CAS ]
  • 23
  • [ 147102-97-4 ]
  • C49H31N3S [ No CAS ]
  • 24
  • [ 147102-97-4 ]
  • [ 864377-31-1 ]
  • C31H20ClN3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 12.0h;Reflux; Inert atmosphere; Reagent 7-1 (100.0 g, 257.55 mmol) and Reagent 2 (58.5 g, 206.43 mmol) were put into 1,000 ml of tetrahydrofuran under a nitrogen atmosphere, and the resulting mixture was stirred and refluxed. Thereafter, potassium carbonate (71.2 g, 515.11 mmol) was dissolved in 200 ml of water, the resulting solution was introduced into the mixture, the resulting mixture was sufficiently stirred, and then tetrakistriphenyl-phosphinopalladium (8.9 g, 7.73 mmol) was introduced thereinto. After the reaction for 12 hours, the temperature of the product was lowered to normal temperature and a produced solid was filtered. After the filtration, the solid was washed with 100 ml of tetrahydrofuran, 500 ml of ethyl acetate, 500 ml of water, and 300 ml of ethanol. The resulting product was dried to prepare Compound 7A (98.6 g, 77%). Reagents 7-1 and 2 were purchased from Aldrich and TCI, respectively.
71% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 8.0h;Inert atmosphere; Reflux; In a nitrogen atmosphere 2- (3-bromophenyl) 4,6-diphenyl-1,3,5-triazine(Reagent 19-1, 50 g, 129 mmol) in tetrahydrofuran (20 mL) was added dropwise to a solution of 2- (3-bromophenyl)And (4-chloronaphthalen-1-yl) boronic acid(4-chloronaphthalen-1-yl) boronic acid (reagent 19-2, 29.2 g, 142 mmol)Was dissolved in 600 ml of tetrahydrofuranAnd stirred and refluxed. After this, potassium carbonate (53 g, 386 mmol)60 ml of waterAfter thorough stirringTetrakis triphenylphosphino palladium (4.5 g, 4 mmol)Respectively.After 8 hours of reaction, the temperature was lowered to room temperature and filtered.The filtrate was extracted with chloroform and water, and then the organic layer was dried with magnesium sulfate.The organic layer was then distilled under reduced pressure and recrystallized using ethyl acetate.The resulting solid was filtered and dried to give Intermediate 19-1 (43 g, 71%).
  • 25
  • [ 147102-97-4 ]
  • [ 864377-31-1 ]
  • C43H27N3S [ No CAS ]
  • 26
  • [ 147102-97-4 ]
  • C26H15ClN2S [ No CAS ]
  • C36H21ClN2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 5.0h;Reflux; (1.0 eq) of Intermediate 5-1, 9.72 g (1.0 eq) of 4-chloronaphthalen-1-yl boronic acid and Pd (PPh3) 4 (0.005 eq) was dissolved in 200 ml of THF, 6.83 g (1.05 eq) of K2CO3 dissolved in water was added, and the mixture was refluxed and stirred. After 5 hours After the reaction was completed, the solution was cooled and the aqueous layer was removed, and the organic solvent was removed by decompression. Afterwards, it was completely dissolved in CHCl3, After washing and decompression, the solvent was removed by about 50%. The mixture was refluxed and ethyl acetate was added thereto. It was cooled and filtered. This was subjected to column chromatography to obtain 18.37 g (yield: 71%) of intermediate 5.
  • 27
  • [ 147102-97-4 ]
  • 2-([1,1'-biphenyl]-4-yl)-4-(4-bromophenyl)-6-phenyl-1,3,5-triazine [ No CAS ]
  • C37H24ClN3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 12.0h;Inert atmosphere; Reflux; Reagent 4-1 (100.0 g, 215.35 mmol) and Reagent 2 (48.9 g, 236.88 mmol) were put into 1,000 ml of tetrahydrofuran under a nitrogen atmosphere, and the resulting mixture was stirred and refluxed. Thereafter, potassium carbonate (59.5 g, 430.69 mmol) was dissolved in 200 ml of water, the resulting solution was introduced thereinto, the resulting mixture was sufficiently stirred, and then tetrakistriphenyl-phosphinopalladium (7.5 g, 6.46 mmol) was introduced thereinto. After the reaction for 12 hours, the temperature of the product was lowered to normal temperature and a produced solid was filtered. After the filtration, the solid was washed with 100 ml of tetrahydrofuran, 500 ml of ethyl acetate, 500 ml of water, and 300 ml of ethanol. The resulting product was dried to prepare Compound 4A (103 g, 85%). Reagents 4-1 and 2 were purchased from Aldrich and TCI, respectively.
  • 28
  • [ 147102-97-4 ]
  • [ 3842-55-5 ]
  • 2-(4-chloronaphthalen-1-yl)-4,6-diphenyl-1,3,5-triazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 12.0h;Reflux; Inert atmosphere; Reagent 6-1 (50.0 g, 187.27 mmol) and Reagent 2 (42.5 g, 205.99 mmol) were put into 1,000 ml of tetrahydrofuran under a nitrogen atmosphere, and the resulting mixture was stirred and refluxed. Thereafter, potassium carbonate (51.8 g, 374.53 mmol) was dissolved in 200 ml of water, the resulting solution was introduced into the mixture, the resulting mixture was sufficiently stirred, and then tetrakistriphenyl-phosphinopalladium (6.5 g, 5.62 mmol) was introduced thereinto. After the reaction for 12 hours, the temperature of the product was lowered to normal temperature and a produced solid was filtered. After the filtration, the solid was washed with 100 ml of tetrahydrofuran, 500 ml of ethyl acetate, 500 ml of water, and 300 ml of ethanol. The resulting product was dried to prepare Compound 6A (52.3 g, 71%). Reagents 6-1 and 2 were purchased from Aldrich and TCI, respectively.
  • 29
  • [ 147102-97-4 ]
  • C37H32BN3O2 [ No CAS ]
  • 30
  • [ 147102-97-4 ]
  • C37H23Cl2N3 [ No CAS ]
  • 31
  • [ 147102-97-4 ]
  • C49H47B2N3O4 [ No CAS ]
  • 32
  • [ 147102-97-4 ]
  • C47H31N5 [ No CAS ]
  • 33
  • [ 147102-97-4 ]
  • C47H31N5 [ No CAS ]
  • 34
  • [ 147102-97-4 ]
  • C47H31N5 [ No CAS ]
  • 35
  • [ 147102-97-4 ]
  • C43H36BN3O2 [ No CAS ]
  • 36
  • [ 147102-97-4 ]
  • C43H27Cl2N3 [ No CAS ]
  • 37
  • [ 147102-97-4 ]
  • C55H51B2N3O4 [ No CAS ]
  • 38
  • [ 147102-97-4 ]
  • C53H35N5 [ No CAS ]
  • 39
  • [ 147102-97-4 ]
  • C59H39N5 [ No CAS ]
  • 40
  • [ 147102-97-4 ]
  • C31H28BN3O2 [ No CAS ]
  • 41
  • [ 147102-97-4 ]
  • C31H19Cl2N3 [ No CAS ]
  • 42
  • [ 147102-97-4 ]
  • C43H43B2N3O4 [ No CAS ]
  • 43
  • [ 147102-97-4 ]
  • C53H35N5 [ No CAS ]
  • 44
  • [ 147102-97-4 ]
  • C37H32BN3O2 [ No CAS ]
  • 45
  • [ 147102-97-4 ]
  • C37H23Cl2N3 [ No CAS ]
  • 46
  • [ 147102-97-4 ]
  • C49H47B2N3O4 [ No CAS ]
  • 47
  • [ 147102-97-4 ]
  • C47H31N5 [ No CAS ]
  • 48
  • [ 856851-34-8 ]
  • [ 147102-97-4 ]
  • 3-(4-chloro-1-naphthyl)pyridine-2,6-diamine hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% General procedure: In a microwave vial, to a suspension of aryl iodide (1.0 eq.) and aryl boronic acid (1.0- 2.5 eq.) in dioxane (C = 0.2 M) was added dropwise an aqueous solution of K2CO3 (1.2 M, 2.0 eq.). The resulting suspension was degassed with argon bubbling for 15 min and PdP(/Bu) PdG2 (7 mol%) was then added in one portion. The vial was sealed and the mixture was stirred at 80 C until no more evolution was noticed by UPLC-MS (overnight, unless mentioned otherwise). The reaction mixture was cooled to rt, filtered on a Celite pad and the cake was washed with MeOH. The filtrate was concentrated in vacuo and the residue was purified. The obtained solid was further purified when necessary. For specific examples, the corresponding hydrochloride salt has been prepared.
  • 49
  • [ 147102-97-4 ]
  • C22H21Cl [ No CAS ]
  • C32H27Cl [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With tetrakis(triphenylphosphine) palladium(0); tetrabutyl-ammonium chloride; potassium carbonate; In ethanol; water; toluene; at 78.0℃; for 16.0h;Inert atmosphere; Intermediate I-A (3.0 g, 9.45 mmol), <strong>[147102-97-4]4-chloro-1-naphthalene boronic acid</strong> (1.3 g, 6.30 mmol),Tetrakistriphenylphosphine palladium (0.15 g, 0.13 mmol), potassium carbonate (1.74 g, 12.6 mmol), tetrabutylammonium chloride (0.09 g, 0.31 mmol), toluene (25 mL), ethanol (6 mL) and deionized Water (6 mL) was added to a round bottom flask, and the temperature was raised to 78 C under nitrogen atmosphere, and stirred for 16 hours;The reaction solution was cooled to room temperature, extracted with toluene (30 mL), and the organic phase was combined.Drying with anhydrous magnesium sulfate, filtration, and removing the solvent under reduced pressure;The obtained crude product was purified by silica gel column chromatography using n-heptane as a mobile phase.After that, it was recrystallized and purified with a dichloromethane/ethyl acetate system.The white solid intermediate I-A-3 (1.89 g, 67%) was obtained.
  • 50
  • [ 147102-97-4 ]
  • [ 37038-69-0 ]
  • C44H29Cl [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 85.0℃; for 6.0h;Inert atmosphere; Toluene / EtOH / H2O (at a volume ratio of 4/2/1, 250 ml) was added to the intermediate compound C (10.2 g, 20 mmol) used in the synthesis of compound A4, and boric acid B2 (4.1 g, 20 mmol) And K3PO4 (8.5 g, 40 mmol), and the product was degassed. Under an argon atmosphere, 2-dicyclohexylphosphino-2 ', 6'-dimethoxybiphenyl (1.6 mg, 4.0 mmol) and tetrakis (triphenylphosphine) palladium (1.6 g, 1.0 mmol) were added Into it,It was then heated at about 85 C and stirred for about 6 hours. The reaction solution was cooled to room temperature, extracted with toluene, washed with water (H2O) and brine solution,And dried over Na2SO4. The solution thus obtained was concentrated and separated by silica gel column chromatography to obtain intermediate compound D(9.1g, 15mmol, yield 77%,
  • 51
  • [ 147102-97-4 ]
  • [ 1342819-12-8 ]
  • [ 2639900-27-7 ]
YieldReaction ConditionsOperation in experiment
67% With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In tetrahydrofuran; water monomer for 8h; Inert atmosphere; Reflux; 1-30 Preparation Example 1-30 Compound sub2 (15 g, 47.2 mmol) and Compound C (9.7 g, 47.2 mmol) were added to THF (300 ml) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (19.6 g, 141.6 mmol) was dissolved in water (59 ml), added thereto, and the mixture was sufficiently stirred and then tetrakis(triphenylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After the reaction for 8 hours, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and then the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give Compound subC-2 (14 g). (Yield: 67%, MS: [M+H]+=444)
  • 52
  • [ 147102-97-4 ]
  • [ 57774-35-3 ]
  • [ 2770820-38-5 ]
YieldReaction ConditionsOperation in experiment
88.1 % With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 90℃; 35 Synthesis of intermediate (51) (4-chloronaphthalen-1-yl)boronic acid ((4-chloronaphthalen-1-yl)boronic acid) 18.0 g (87.2 mmol), 4'-bromo-[1,1'-biphenyl]-4- Carbonitrile (4'-bromo-[1,1'-biphenyl]-4-carbonitrile) 15.0 g (58.1 mmol), Pd(PPh3)41.34 g (1.16 mmol), K2CO324.1 g (174 mmol) ), 150 mL of toluene, 37.5 mL of ethanol and 37.5 mL of distilled water were added.The reaction mixture was stirred at 90 °C for 3 hours.After adding 50 mL of distilled water, the layers were separated to obtain an organic layer.After drying over anhydrous sodium sulfate, the mixture was filtered and concentrated in vacuo to remove the solvent.After heating and dissolving the obtained reactant in MC, it was passed through a silica gel pad.Recrystallization from DCM and n-Hexanegave 17.4 g (yield: 88.1%) of the compound (Intermediate (51)) as a white solid.
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