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[ CAS No. 689260-53-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 689260-53-5
Chemical Structure| 689260-53-5
Chemical Structure| 689260-53-5
Structure of 689260-53-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 689260-53-5 ]

CAS No. :689260-53-5 MDL No. :MFCD07780650
Formula : C8H8BrI Boiling Point : -
Linear Structure Formula :- InChI Key :QFHHDLIXCIGLBS-UHFFFAOYSA-N
M.W : 310.96 Pubchem ID :20748037
Synonyms :

Calculated chemistry of [ 689260-53-5 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 56.79
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.36 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.73
Log Po/w (XLOGP3) : 3.99
Log Po/w (WLOGP) : 3.67
Log Po/w (MLOGP) : 4.53
Log Po/w (SILICOS-IT) : 4.39
Consensus Log Po/w : 3.86

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.73
Solubility : 0.00585 mg/ml ; 0.0000188 mol/l
Class : Moderately soluble
Log S (Ali) : -3.69
Solubility : 0.0633 mg/ml ; 0.000203 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.96
Solubility : 0.00343 mg/ml ; 0.000011 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.91

Safety of [ 689260-53-5 ]

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 [ 689260-53-5 ]

* 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 [ 689260-53-5 ]

[ 689260-53-5 ] Synthesis Path-Downstream   1~62

  • 1
  • [ 689260-53-5 ]
  • [ 144653-01-0 ]
  • 4
  • [ 689260-53-5 ]
  • [ 122-39-4 ]
  • (4-bromo-3,5-dimethylphenyl)diphenylamine [ No CAS ]
  • 5
  • [ 689260-53-5 ]
  • [ 856197-59-6 ]
  • 6
  • [ 689260-53-5 ]
  • 4,4'-bis[bis(2,4,6-triisopropylphenyl)phosphino]-3,3'5,5'-tetramethylbiphenyl [ No CAS ]
  • 7
  • [ 689260-53-5 ]
  • 2-bromo-1,3-bis(hydroxymethyl)-5-iodobenzene [ No CAS ]
  • 8
  • [ 689260-53-5 ]
  • [ 312304-54-4 ]
  • 9
  • [ 64835-48-9 ]
  • [ 689260-53-5 ]
  • 11
  • [ 689260-53-5 ]
  • [ 1332883-42-7 ]
  • 12
  • [ 689260-53-5 ]
  • [ 1332883-47-2 ]
  • 13
  • [ 689260-53-5 ]
  • [ 1332883-49-4 ]
  • 14
  • [ 689260-53-5 ]
  • [ 1332883-50-7 ]
  • 15
  • [ 689260-53-5 ]
  • [ 1332883-51-8 ]
  • 16
  • [ 689260-53-5 ]
  • [ 1332883-43-8 ]
  • 17
  • [ 689260-53-5 ]
  • [ 1332883-44-9 ]
  • 18
  • [ 689260-53-5 ]
  • [ 756873-19-5 ]
  • 19
  • [ 689260-53-5 ]
  • [ 89343-06-6 ]
  • [ 1332883-54-1 ]
  • 20
  • [ 689260-53-5 ]
  • dichloro(2,6-dimethyl-4-(N-phenothiazinyl)phenyl)phosphine [ No CAS ]
  • 21
  • [ 689260-53-5 ]
  • 2-bromo-1,3-dimethyl-5-(N-phenothiazinyl)benzene [ No CAS ]
  • 22
  • [ 689260-53-5 ]
  • [ 92-84-2 ]
  • [ 1334106-54-5 ]
YieldReaction ConditionsOperation in experiment
With copper; potassium carbonate; In N,N-dimethyl-formamide; at 130℃; for 24h;Inert atmosphere; 2-Bromo-4-iodo1,3-xylene (10 mmol), 5,10-phenothiazine (10 mmol), Cu (20 mmol), under a nitrogen atmosphereK2CO3 (20 mmol) and N,N-dimethylformamide (20 ml) were combined to form a solution.The above mixed solution was evacuated three times with nitrogen, and heated and stirred at 130 C for 24 h. The reaction mixture was filtered through celite and usedWash with dichloromethane (20 ml).The solvent was evaporated under reduced pressure and purified by column chromatography (hexane/dichloromethane 10:1) to give the product 10-(4-bromo-3,5-dimethylphenyl)-phenothiazine S25-1 .
  • 23
  • [ 689260-53-5 ]
  • [ 173382-28-0 ]
  • [ 1458656-32-0 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 100℃; for 3h;Inert atmosphere; 2-(4-Bromo-3,5-dimethyl-phenyl)-thiazole A mixture of 2-bromo-5-iodo-1,3-dimethyl-benzene (0.28 g), 2-thiazolylzinc bromide (0.5 mol/L in tetrahydrofuran; 1.9 mL), tetrakis(triphenylphosphine)palladium(0) (52 mg), and tetrahydrofuran (5 mL) under argon atmosphere is stirred at 100 C. for 3 h. After cooling to room temperature, water is added and the resulting mixture is extracted with ethyl acetate. The solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate) to give the title compound. LC (method 9): tR=1.19 min; Mass spectrum (ESI+): m/z=268/270 (Br) [M+H]+.
  • 24
  • [ 689260-53-5 ]
  • [ 288-88-0 ]
  • [ 1458655-27-0 ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 130 - 150℃; Step 1: 1-(4-Bromo-3,5-dimethylphenyl)-1H-1,2,4-triazole A mixture of <strong>[689260-53-5]2-bromo-5-iodo-1,3-dimethylbenzene</strong> (500 mg), 1,2,4-triazole (340 mg), potassium carbonate (770 mg), and copper(I) iodide (232 mg) in N-methyl-2-pyrrolidinone is stirred at 130 C. over night. More potassium carbonate (770 mg) and copper(I) iodide (232 mg) are added and the mixture is heated to 150 C. for 4 h. After cooling to room temperature the mixture is diluted with tetrahydrofuran and filtered. The filtrate is concentrated in vacuo and purified by HPLC on reversed phase to give the title compound. LC (method 7): tR=0.99 min; Mass spectrum (ESI+): m/z=252, 254 [M+H]+.
With copper(l) iodide; potassium carbonate; at 130 - 150℃; A mixture of 2-bromo-5-iodo-1 ,3-dimethylbenzene (500 mg), 1 ,2,4-triazole (340 mg), potassium carbonate (770 mg), and copper(l) iodide (232 mg) in N-methyl-2- pyrrolidinone is stirred at 130 C over night. More potassium carbonate (770 mg) and copper(l) iodide (232 mg) are added and the mixture is heated to 150 C for 4 h. After cooling to room temperature the mixture is diluted with tetrahydrofuran and filtered. The filtrate is concentrated in vacuo and purified by HPLC on reversed phase to give the title compound. LC (method 7): tR = 0.99 min; Mass spectrum (EST): m/z = 252, 254 [M+H]+.
  • 27
  • [ 689260-53-5 ]
  • [ 321724-19-0 ]
  • [ 1458652-87-3 ]
YieldReaction ConditionsOperation in experiment
446 mg With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In water; N,N-dimethyl-formamide; at 60℃; for 3.0h;Inert atmosphere; Sealed tube; Step 1: 5-(4-Bromo-3,5-dimethylphenyl)pyrimidine In a microwave vial <strong>[689260-53-5]2-bromo-5-iodo-1,3-dimethylbenzene</strong> (1 g) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine (665 mg) are suspended in N,N-dimethylformamide (15 mL) and Na2CO3 (4 mL of a 2 M aqueous solution). The mixture is purged for 5 minutes with argon. [1,1'-Bis(diphenylphosphino)-ferrocene]-dichloropalladium dichloromethane complex (85 mg) is added, the vial is sealed and the mixture is stirred at 60° C. for 3 hours. After cooling to room temperature the mixture is Partitioned between water and ethyl acetate. The aqueous phase is extracted with ethyl acetate and the combined organic phases are washed with brine. Then the organic phase is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 80:20?50:50) to give the title compound. Yield: 446 mg; LC (method 9): tR=1.05 min; Mass spectrum (ESI+): m/z=263 [M+H]+.
446 mg With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In water; N,N-dimethyl-formamide; at 60℃; for 3.0h;Microwave irradiation; Sealed tube; Inert atmosphere; In a microwave vial 2-bromo-5-iodo-1 ,3-dimethylbenzene (1 g) and 5-(4,4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyrimidine (665 mg) are suspended in N,N- dimethylformamide (15 mL) and Na2CO3 (4 mL of a 2 M aqueous solution). The mixture is purged for 5 minutes with argon. [1 ,1 '-Bis(diphenylphosphino)-ferrocene]- dichloropalladium dichloromethane complex (85 mg) is added, the vial is sealed and the mixture is stirred at 60°C for 3 hours. After cooling to room temperature the mixture is Partitioned between water and ethyl acetate. The aqueous phase is extracted with ethyl acetate and the combined organic phases are washed with brine. Then the organ ic phase is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 80:20?50:50) to give the title compound. Yield: 446 mg; LC (method 9): tR = 1 .05 min; Mass spectrum (EST): m/z = 263 [M+H]+.
446 mg With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In water; N,N-dimethyl-formamide; at 60℃; for 3.0h;Inert atmosphere; Microwave irradiation; Sealed tube; In a microwave vial 2-bromo-5-iodo-1 ,3-dimethylbenzene (1 g) and 5-(4,4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyrimidine (665 mg) are suspended in N,N- dimethylformamide (15 mL) and Na2CO3 (4 mL of a 2 M aqueous solution). The mixture is purged for 5 minutes with argon. [1 ,1 '-Bis(diphenylphosphino)-ferrocene]- dichloropalladium dichloromethane complex (85 mg) is added, the vial is sealed and the mixture is stirred at 60°C for 3 hours. After cooling to room temperature the mixture is Partitioned between water and ethyl acetate. The aqueous phase is extracted with ethyl acetate and the combined organic phases are washed with brine. Then the organ ic phase is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 80:20?50:50) to give the title compound. Yield: 446 mg; LC (method 9): tR = 1 .05 min; Mass spectrum (ESI+): m/z = 263 [M+H]+.
  • 28
  • [ 689260-53-5 ]
  • [ 73183-34-3 ]
  • [ 1073338-97-2 ]
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In dimethyl sulfoxide; at 20 - 90℃; for 3h;Inert atmosphere; Step 1: 2-bromo-1,3-dimethyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzene A flask charged with a stir bar, 2-bromo-5-iodo-1,3-dimethyl-benzene (1.0 g), bis-(pinacolato)-diboron (1.0 g), potassium acetate (1.1 g) and dimethyl sulfoxide (10 mL) is purged with argon for 5 min. [1,1'-Bis(diphenylphosphino)-ferrocene]-dichloropalladium(II) (0.26 g) is added at room temperature, and the mixture is stirred at 90 C. for 3 h. After cooling to room temperature, water is added and the resulting mixture is extracted with ethyl acetate. The combined extracts are dried (MgSO4) and concentrated. The residue is chromatographed on reversed phase (HPLC; acetonitrile/water) to give the title compound. LC (method 9): tR=1.30 min; Mass spectrum (ESI+): m/z=311/313 (Br) [M+H]+.
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In dimethyl sulfoxide; at 90℃; for 3h;Inert atmosphere; A flask charged with a stir bar, 2-bromo-5-iodo-1 ,3-dimethyl-benzene (1 .0 g), bis- (pinacolato)-diboron (1 .0 g), potassium acetate (1 .1 g) and dimethyl sulfoxide (10 ml_) is purged with argon for 5 min. [1 ,1 '-Bis(diphenylphosphino)-ferrocene]- dichloropalladium(ll) (0.26 g) is added at room temperature, and the mixture is stirred at 90 C for 3 h. After cooling to room temperature, water is added and the resulting mixture is extracted with ethyl acetate. The combined extracts are dried (MgSO4) and concentrated. The residue is chromatographed on reversed phase (HPLC; acetonitrile/water) to give the title compound . LC (method 9): tR = 1 .30 min; Mass spectrum (ESI+): m/z = 31 1/313 (Br) [M+H]+.
  • 29
  • [ 689260-53-5 ]
  • 2-methyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propan-2-ol [ No CAS ]
  • [ 1458655-14-5 ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In water; N,N-dimethyl-formamide; at 60℃; for 3h;Inert atmosphere; Step 1: 1-(4-(4-Bromo-3,5-dimethylphenyl)-1H-pyrazol-1-yl)-2-methylpropan-2-ol A mixture of <strong>[689260-53-5]2-bromo-5-iodo-1,3-dimethylbenzene</strong> (1.00 g), 2-methyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propan-2-ol (1.11 g), and 2 M aqueous Na2CO3 solution (4.0 mL) in N,N-dimethylformamide is purged with argon for 3 min. [1,1'-Bis(diphenylphosphino)-ferrocene]-dichloropalladium dichloromethane complex (85 mg) is added and the mixture is stirred at 60 C. for 3 h. After cooling to room temperature the mixture is diluted with water and ethyl acetate. The organic phase is washed with brine, dried over MgSO4 and concentrated in vacuo. The residue is purified by HPLC on reversed phase to give the title compound. LC (method 11): tR=1.12 min; Mass spectrum (ESI+): m/z=323, 325 [M+H]+.
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In N,N-dimethyl-formamide; at 60℃; for 3h;Inert atmosphere; A mixture of 2-bromo-5-iodo-1 ,3-dimethylbenzene (1 .00 g), 2-methyl-1 -(4-(4,4,5,5- tetramethyl-1 , 3, 2-dioxaborolan-2-yl)-1 H-pyrazol-1 -yl)propan-2-ol (1 .1 1 g), and 2 M aqueous Na2CO3 solution (4.0 ml_) in Nu,Nu-dimethylformamide is purged with argon for 3 min. [1 ,1 '-Bis(diphenylphosphino)-ferrocene]-dichloropalladium dichloromethane complex (85 mg) is added and the mixture is stirred at 60 C for 3 h. After cooling to room temperature the mixture is diluted with water and ethyl acetate. The organic phase is washed with brine, dried over MgSO4 and concentrated in vacuo. The residue is purified by HPLC on reversed phase to give the title compound. LC (method 1 1 ): tR = 1 .12 min; Mass spectrum (ESI+): m/z = 323, 325 [M+H]+.
  • 30
  • [ 689260-53-5 ]
  • [ 55552-70-0 ]
  • [ 1458655-31-6 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 100℃;Inert atmosphere; A mixture of 2,5-dibromo-1 ,3-dimethylbenzene (2.00 g), 1 -furan-3-ylboronic acid (856 mg), and 2 M aqueous Na2CO3 solution (1 1 ml_) in 1 ,4-dioxane (40 ml_) is purged with argon for 5 min. Tetrakis-triphenylphosphine-palladium-(O) (270 mg) is added and the mixture is stirred at 100 C over n ight. More tetrakis- triphenylphosphine-palladium-(O) (50 mg) is added and the mixture is stirred for another 5 h at 100 C. After cooling to room temperature the mixture is diluted with ethyl acetate and aqueous NH CI solution. The aqueous phase is extracted with ethyl acetate and the combined extracts are washed with brine, dried over MgSO4 and concentrated in vacuo. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 100:0?90:10) to give the title compound. LC (method 7): tR = 1 .22 min; Mass spectrum (Epsilon ): m/z = 250 [M]+
  • 31
  • [ 689260-53-5 ]
  • [ 1458655-33-8 ]
  • 32
  • [ 689260-53-5 ]
  • [ 22059-21-8 ]
  • 1-((4-bromo-3,5-dimethylphenyl)amino)cyclopropane carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl acetamide; at 120℃; for 3h;Inert atmosphere; A mixture of <strong>[689260-53-5]2-bromo-5-iodo-1,3-dimethylbenzene</strong> (300 mg, 0.965 mmol), 1-aminocyclopropane carboxylic acid (195 mg, 1.93 mmol), copper iodide (I) (37 mg, 0.194 mmol), and diazabicycloundecene (0.50 mL, 3.35 mmol) in dimethylacetamide (2.6 mL) was stirred at 120C for three hours under nitrogen atmosphere. The reaction mixture was purified by silica gel column chromatography (Wakosil C18, acetonitrile - water (0.1% formic acid)) to afford 1-((4-bromo-3,5-dimethylphenyl)amino)cyclopropane carboxylic acid (219 mg, 80%). MS(ESI) m/z = 284, 286 (M+H)+.
80% With copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; at 120℃; for 3h; To 2-Bromo-5-iodo-1,3-Dimethylbenzene(300 mg, 0.965 mmol),1-Amino cyclopropanecarboxylic acid(195 mg, 1.93 mmol),A mixture of copper (I) iodide (37 mg, 0.194 mmol) and diazabicycloundecene (0.50 ml, 3.35 mmol) in dimethylacetamide (2.6 ml) was heated at 120 C for 3 hours under a nitrogen stream Stirring. The reaction mixture was purified by silica gel column chromatography (Wakosil C18, acetonitrile-water (0.1% formic acid)1 - ((4-Bromo-3,5-Dimethylphenyl)Amino)Cyclopropanecarboxylic acid(219 mg, 80%).
80% With copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl acetamide; at 120℃; for 3h;Inert atmosphere; A mixture of <strong>[689260-53-5]2-bromo-5-iodo-1,3-dimethylbenzene</strong> (300 mg, 0.965 mmol), 1-aminocyclopropane carboxylic acid (195 mg, 1.93 mmol), copper iodide (I) (37 mg, 0.194 mmol), and diazabicycloundecene (0.50 mL, 3.35 mmol) in dimethylacetamide (2.6 mL) was stirred at 120 C. for three hours under nitrogen atmosphere. The reaction mixture was purified by silica gel column chromatography (Wakosil C18, acetonitrile-water (0.1% formic acid)) to afford 1-((4-bromo-3,5-dimethylphenyl)amino)cyclopropane carboxylic acid (219 mg, 80%). MS(ESI) m/z=284, 286 (M+H)+.
  • 33
  • [ 689260-53-5 ]
  • N,N-diphenyl-9H-carbazole-3-amine [ No CAS ]
  • C32H25BrN2 [ No CAS ]
  • 35
  • [ 689260-53-5 ]
  • [ 135-67-1 ]
  • 10-(4-bromo-3,5-dimethylphenyl)-10H-phenoxazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper; potassium carbonate; In N,N-dimethyl-formamide; at 130℃; for 24h;Inert atmosphere; 2-bromo-5-iodo1,3-dimethylbenzene (10 mmol), phenoxazine (10 mmol), Cu (20 mmol), under a nitrogen atmosphereK2CO3 (20 mmol) and N,N-dimethylformamide (20 ml) were combined to form a solution.The above mixed solution was evacuated three times with nitrogen, and heated and stirred at 130 C for 24 h. The reaction mixture was filtered through celite and usedWash with dichloromethane (20 ml).The solvent was evaporated under reduced pressure and purified by column chromatography (hexane/dichloromethane: 10:1) to yield 10-(4-bromo-3,5-dimethylphenyl)-phenoxazine S5- 1.
  • 36
  • [ 689260-53-5 ]
  • [ 608527-58-8 ]
  • C44H34BrN3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With copper(l) iodide; potassium carbonate; L-proline; In N,N-dimethyl-formamide; at 110℃; for 48h;Inert atmosphere; Under an argon atmosphere, Intermediate 6 (1.20 g, 2.40 mmol), 2-Bromo-5-iodo-1,3-dimethylbenzene (Intermediate 15) (893 mg, 2.88 mmol)(1.68 g, 4.80 mmol, manufactured by Wako Pure Chemical Industries, Ltd.) and copper iodide (91.4 mg, 0.48 mmol, 0.35 mmol) were added to a solution of L-proline (110 mg, 0.96 mmol; manufactured by Wako Pure Chemical Industries, (Manufactured by Wako Pure Chemical Industries, Ltd.) Dimethylformamide (2.4 ml, manufactured by Wako Pure Chemical Industries, Ltd.) was heated to 110 C under an argon atmosphere for 48 hours. to the next,After cooling to room temperature, saturated aqueous ammonium chloride solution (30 ml) and dichloromethane (100 ml) were added to the reaction mixture and the layers were separated. The organic layer was dried over magnesium sulfate and the residue was purified by silica gel column chromatography (dichloromethane 20% Hexane 80%) to obtain Intermediate 16 as pale yellow crystals (1.49 g, yield 91%).
  • 37
  • [ 689260-53-5 ]
  • 4-(4-bromo-3,5-dimethylphenyl)-4,6-diazaspiro[2.4]heptane-5,7-dione [ No CAS ]
  • 38
  • [ 689260-53-5 ]
  • N,N’,N’’-triphenyl-B,B’,B’’-tri(2,6-dimethyl-4-ethynylphenyl)borazine [ No CAS ]
  • 39
  • [ 689260-53-5 ]
  • [ 1066-54-2 ]
  • ((4-bromo-3,5-dimethylphenyl)ethynyl)trimethylsilane [ No CAS ]
  • 40
  • [ 689260-53-5 ]
  • [ 1066-54-2 ]
  • N,N’,N’’-triphenyl-B,B’,B’’-tri(2,6-dimethyl-4-(trimethylsilylethynyl)phenyl)borazine [ No CAS ]
  • 41
  • [ 689260-53-5 ]
  • [ 66476-86-6 ]
  • C17H21BrO2 [ No CAS ]
  • 42
  • [ 689260-53-5 ]
  • C25H41NO3Si [ No CAS ]
  • 43
  • [ 689260-53-5 ]
  • C30H41Cl2N3O4Si [ No CAS ]
  • 44
  • [ 689260-53-5 ]
  • C24H27Cl2N3O4 [ No CAS ]
  • 45
  • [ 689260-53-5 ]
  • C24H26ClN3O4 [ No CAS ]
  • 46
  • [ 689260-53-5 ]
  • C22H24N4O4 [ No CAS ]
  • 47
  • [ 689260-53-5 ]
  • C24H28N4O4 [ No CAS ]
  • 48
  • [ 689260-53-5 ]
  • (3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydrofuran-3-ol [ No CAS ]
  • [(3R,4R)-4-(4-bromo-3,5-dimethyl-phenoxy)-tetrahydro-furan-3-yloxy]-tert-butyl-dimethyl-silane [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate; In toluene; at 115℃; CuI (0.12 g) and 1,10-phenanthroline (0.23 g) are added to a flask charged with a stir bar, <strong>[689260-53-5]2-bromo-5-iodo-m-xylene</strong> (2.00 g), (3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydrofuran-3-ol (1.72 g), Cs2CO3 (4.11 g), and toluene (10 mL) at room temperature. The mixture is stirred at 115 C. overnight. After cooling to room temperature, water is added, and the resulting mixture is extracted with ethyl acetate. The combined extract is washed with aqueous 1 M HCl solution and dried (MgSO4). The solvent is evaporated, and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 49:1) to give the title compound. Mass spectrum (ESI+): m/z=401/403 (Br) [M+H]+.
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate; In toluene; at 20 - 115℃; Step 1: [(3R,4R)-4-(4-Bromo-3,5-dimethyl-phenoxy)-tetrahydrofuran-3-yloxy]-tert-butyl-dimethyl-silane CuI (0.12 g) and 1,10-phenanthroline (0.23 g) are added to a flask charged with a stir bar, <strong>[689260-53-5]2-bromo-5-iodo-m-xylene</strong> (2.00 g), (3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydrofuran-3-ol (1.72 g), Cs2CO3 (4.11 g), and toluene (10 mL) at room temperature. The mixture is stirred at 115 C. overnight. After cooling to room temperature, water is added, and the resulting mixture is extracted with ethyl acetate. The combined extract is washed with aqueous 1 M HCl solution and dried (MgSO4). The solvent is evaporated, and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 49:1) to give the title compound. Mass spectrum (ESI): m/z=401/403 (Br) [M+H]+.
  • 49
  • [ 689260-53-5 ]
  • (3R,4R)-4-[4-((R)-1-amino-7-fluoro-indan-4-yl)-3,5-dimethyl-phenoxy]-tetrahydro-furan-3-ol [ No CAS ]
  • 50
  • [ 689260-53-5 ]
  • ((R)-4-{4-[(3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-3-yloxy]-2,6-dimethyl-phenyl}-7-fluoro-indan-1-yl)-carbamic acid tert-butyl ester [ No CAS ]
  • 51
  • [ 689260-53-5 ]
  • [ 365564-05-2 ]
  • 1,3,5-tris(4-bromo-3,5-dimethylphenyl)benzene [ No CAS ]
  • 52
  • [ 689260-53-5 ]
  • [ 388116-27-6 ]
  • C16H16BrN [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; toluene; for 8h;Inert atmosphere; Reflux; the obtained 38-6-a (3.92 g, 20 mmol), Bis(pinacolato)diboron (6.22 g, 24 mmol), 1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (0.49 g, 0.6 mmol), potassium acetate (5.90 g, 60 mmol) and 79 ml of toluene were reacted under reflux for 16 hours.After cooling, 26 ml of water was added and stirred for 30 minutes, the organic phase was separated, filtered through a short bed of celite, soon afterwards the organic solvent was evaporated off, and the obtained crude product was recrystallized from heptane / toluene; Under argon atmosphere, the obtained solid 38-6-b (3.65g, 15mmol), 38-6-c (4.45g, 14.3mmol), Tetrakis(triphenylphosphine)palladium (0·35 g, 0.3 mmol), toluene (43 ml), aqueous sodium carbonate (2M, 21 ml) was added to the flask and refluxed for 8 hours.After cooling to room temperature, it was extracted with toluene, and the organic phase was washed with brine, and then dried, and then purified by column chromatography to obtain bromide 38-6-d; Tri-tert-butylphosphine (4.4 mL of a 1.0 M solution in toluene, 1.48 g, 0.05 mmol), palladium acetate (0.4 g, 1.83 mmol) and sodium tert-butoxide (52.7 g, 549 mmol) were added to a solution of 38-6-d (22.04 g, 73.42 mmol) and bromobenzene (11.53 g, 73.42 mmol) in degassed toluene (500 mL) and the mixture was Heat under reflux for 2 hours. This reaction mixture was cooled to room temperature, diluted with toluene and filterated through celite. This filtrate was diluted with water and extracted with toluene, and the organic phases were combined and evaporated in vacuo. This residue was filtered through silica gel (heptane / dichloromethane) and crystallised from isopropyl alcohol to give compound 38-6-e;the obtained 38-6-a (3.92 g, 20 mmol), Bis(pinacolato)diboron (6.22 g, 24 mmol), 1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (0.49 g, 0.6 mmol), potassium acetate (5.90 g, 60 mmol) and 79 ml of toluene were reacted under reflux for 16 hours.After cooling, 26 ml of water was added and stirred for 30 minutes, the organic phase was separated, filtered through a short bed of celite, soon afterwards the organic solvent was evaporated off, and the obtained crude product was recrystallized from heptane / toluene to obtain compound 38-6.
  • 53
  • [ 689260-53-5 ]
  • [ 871917-01-0 ]
  • C38H33Br [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 90℃; for 16h; 5.5 g (17.8 mmol) of <strong>[689260-53-5]2-bromo-5-iodo-1,3-dimethylbenzene</strong>,6.5 g (12.7 mmol) EG1, 366 mg (0.3 mmol) of tetrakis(triphenylphosphine)-palladium (0)And 2.7 g (13 mmol) of sodium carbonate in 200 mL of toluene,Ethanol and water (2:1:1) were mixed and stirred at 90 C for 16 hours. After cooling to room temperature, 100 mL of toluene was added and the organic phase was separated and washed with water (2×50 mL). The organic phase was concentrated to dryness under reduced pressure.The residue was purified by recrystallization from toluene / heptane.Yield: 6.2 g (11 mmol; 86%).
86% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 90℃; for 16h; 5.5 g (17.8 mmol) 2-Bromo-5-iodo-1 ,3-dimethylbenzene, 6.5 g (12.7 mmol) EG1 , 366 mg (0.3 mmol) tetrakis(triphenylphosphin)-palladium(0) and 2.7 g (13 mmol) sodium carbonate are dissolved in 200 ml toluene, ethanol and water (2:1 :1 ) and stirred for 16 hours at 90 C. After cooling down to room temperature 100 ml toluene are added, the organic phase is separated and washed with water (2x50 ml). The organic phase is concentrated to dryness under reduced pressure. The residue is purified by recrystallization from toluene/heptane. Yield: 6.2 g (11 mmol; 86 %)
86% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 90℃; for 16h; 5.5 g (17.8 mmol) 2-Bromo-5-iodo-1 ,3-dimethylbenzene, 6.5 g (12.7 mmol) BB-003, 366 mg (0.3 mmol) tetrakis(thphenylphosphin)-palladium(0) and 2.7 g (13 mmol) sodium carbonate are dissolved in 200 ml toluene, ethanol and water (2:1 :1 ) and stirred for 16 hours at 90 C. After cooling to room temperature, 100 ml toluene are added, the organic phase is separated and washed with water (2x50 ml). The organic phase is concentrated to dryness under reduced pressure. The residue is purified by recrystallization from toluene/heptane. Yield: 6.2 g (11 mmol; 86 %)
86% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 90℃; for 16h; 5.5 g (17.8 mmol) 2-Bromo-5-iodo-1 ,3-dimethylbenzene, 6.5 g (12.7 mmol) EG1 , 366 mg (0.3 mmol) tetrakis(triphenylphosphin)-palladium(0) and 2.7 g (13 mmol) sodium carbonate are dissolved in 200 ml_ toluene, ethanol and water (2:1 :1 ) and stirred for 16 hours at 90 C. After cooling down to room temperature 100 ml toluene are added, the organic phase is separated and washed with water (2 x 50 ml_). The organic phase is concentrated to dryness under reduced pressure. The residue is purified by recrystallization from toluene/heptane. Yield: 6.2 g (11 mmol; 86 %)

  • 54
  • [ 689260-53-5 ]
  • C52H39B2NS [ No CAS ]
  • 55
  • [ 689260-53-5 ]
  • C26H28BNO2S [ No CAS ]
  • 56
  • [ 689260-53-5 ]
  • [ 6267-02-3 ]
  • 9-(4-bromo-3,5-dimethylphenyl)dimethylacridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper; potassium carbonate; In N,N-dimethyl-formamide; at 130℃; for 24h;Inert atmosphere; 2-bromo-5-iodo1,3-xylene (10 mmol), 9,9-dimethyl acridine (10 mmol), Cu under a nitrogen atmosphere(20 mmol), K2CO3 (20 mmol) and N,N-dimethylformamide (20 ml) were combined to form a solution.Mixing the above mixed solution with nitrogenThe vacuum was evacuated three times and heated and stirred at 130 C for 24 h. The reaction mixture was filtered through celite and usedWash with dichloromethane (20 ml).The solvent was evaporated under reduced pressure and purified by column chromatography (hexane/dichloromethane: 10:1) to yield white crystals of 9-(4-bromo-3,5-dimethylphenyl)-dimethyl acridine. S2-1.
  • 57
  • [ 689260-53-5 ]
  • [ 6267-02-3 ]
  • C29H34BNO2 [ No CAS ]
  • 58
  • [ 689260-53-5 ]
  • [ 135-67-1 ]
  • C50H36BN3O2 [ No CAS ]
  • 59
  • [ 689260-53-5 ]
  • [ 64-19-7 ]
  • (4-bromo-3,5-dimethylphenyl)diyldiacetate [ No CAS ]
  • 60
  • [ 689260-53-5 ]
  • 2-(3-bromo-6-iodo-2,4-dimethylphenyl)-2,2-difluoro-1-phenylethan-1-one [ No CAS ]
  • 61
  • [ 689260-53-5 ]
  • [ 1079-66-9 ]
  • 2-bromo-5-(diphenylphosphinoyl)-1,3-dimethyl-benzene [ No CAS ]
  • 62
  • [ 689260-53-5 ]
  • [ 16245-79-7 ]
  • 4-bromo-N-(4-bromo-3,5-dimethylphenyl)-3,5-dimethyl-N-(4-octylphenyl)aniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In toluene at 120℃; for 4h; Inert atmosphere;
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