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[ CAS No. 942282-41-9 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 942282-41-9
Chemical Structure| 942282-41-9
Chemical Structure| 942282-41-9
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Quality Control of [ 942282-41-9 ]

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Product Details of [ 942282-41-9 ]

CAS No. :942282-41-9 MDL No. :MFCD22418249
Formula : C9H8BrFO2 Boiling Point : -
Linear Structure Formula :- InChI Key :GJSFSDMLTLWFQN-UHFFFAOYSA-N
M.W : 247.06 Pubchem ID :71265948
Synonyms :

Calculated chemistry of [ 942282-41-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 49.96
TPSA : 26.3 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) : -6.03 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.51
Log Po/w (XLOGP3) : 2.5
Log Po/w (WLOGP) : 2.72
Log Po/w (MLOGP) : 3.11
Log Po/w (SILICOS-IT) : 3.14
Consensus Log Po/w : 2.8

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.09
Solubility : 0.201 mg/ml ; 0.000812 mol/l
Class : Soluble
Log S (Ali) : -2.7
Solubility : 0.496 mg/ml ; 0.00201 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.02
Solubility : 0.0238 mg/ml ; 0.0000964 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.78

Safety of [ 942282-41-9 ]

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 [ 942282-41-9 ]

* 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 [ 942282-41-9 ]

[ 942282-41-9 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 942282-40-8 ]
  • [ 74-88-4 ]
  • [ 942282-41-9 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In acetonitrile; at 0 - 60℃; Methyl iodide (4.4 niL, 0.071 mol) was added, at O0C, to a suspension of (4- bromo-3-fluorophenyl)acetic acid (8.2 g, 0.035 mol; see step (iii) above) and potassium carbonate (12.2 g, 0.088 mol) in dry acetonitrile (100 mL). The resulting mixture was stirred at 60C overnight under a nitrogen atmosphere. The reaction mixture was filtered and solvent concentrated under reduced pressure to provide 6.4 g of the sub-title compound as pale yellow oil. This was employed directly in the next step without further purification.
  • 2
  • [ 942282-41-9 ]
  • [ 557-21-1 ]
  • [ 444807-50-5 ]
YieldReaction ConditionsOperation in experiment
tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 80℃; A suspension of methyl (4-bromo-3 -fluorophenyl) acetate (6.4 g, 0.026 mol; see step (iv) above) and Zn(CN)2 (2.09 g, 0.018 mol) in dry DMF (32 mL) was evacuated and purged with argon for 15 minutes. Pd(PPli3)4 (1.5 g, 0.0013 mol) was added and the resulting suspension was stirred at 8O0C overnight under an argon atmosphere. The reaction was quenched with water, DMF was evaporated under reduced pressure and the resulting aqueous layer was extracted with ethyl acetate. The organic (ethyl acetate) layer was washed with water and brine and then dried over sodium sulfate. Solvent evaporation under reduced pressure, followed by purification over silica gel using 15% ethyl acetate in petroleum ether as eluent, afforded 4.3 g of the sub-title compound as pale yellow liquid.
  • 3
  • [ 499983-13-0 ]
  • [ 67-56-1 ]
  • [ 942282-41-9 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid;Heating / reflux; Step C: <strong>[499983-13-0](4-bromo-3-fluorophenyl)acetonitrile</strong> (40 g, 0.18 mol) was dissolved in 120 mL methanol, and 65 mL concentrated sulfuric acid were added. After heating at reflux overnight, the reaction mixture was cooled, and poured into 600 mL water, and the product was extracted with CH2Cl2. The combined extracts were washed with 10% sodium carbonate solution, dried, and concentrated to afford methyl (4-bromo-3-fluorophenyl)acetate.
  • 4
  • [ 942282-41-9 ]
  • [ 1021732-05-7 ]
  • [ 1021732-62-6 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-(2,2-dimethylpropyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide With n-butyllithium In tetrahydrofuran; hexane at -70℃; for 1h; Stage #2: methyl 2-(4-bromo-3-fluorophenyl)acetate In tetrahydrofuran; hexane at 20℃; for 1h; D Step D: To a solution of intermediate l (10 g, 0.041 mol) in 210 mL THF at -70 0C was added n-BuLi (1.6 M in hexane, 28 mL, 0.045 mol). The mixture was stirred at - 70 0C for 1 h, then a solution of methyl (4-bromo-3-fluorophenyl)acetate (10.1 g, 0.041 mol) in 10 mL THF was added. The reaction mixture was allowed to warm to room temperature and stirred for another hour. The reaction was quenched with ice-water (200 mL), and the product extracted with CH2Cl2. The extracts were dried over MgSO4, filtered and concentrated. Column chromatography (2% EtOAc/PE) of the residue afforded the title compound.
  • 5
  • [ 67-56-1 ]
  • [ 942282-40-8 ]
  • [ 942282-41-9 ]
YieldReaction ConditionsOperation in experiment
84% With thionyl chloride; at 0 - 50℃; for 4h; To a 100 mL rotmd-hottom f1ask vas added 2-(4-hromo-3-f1uorophenyl)acetic acid153b (2 g, 8.58 mmol, 1.00 equiv.) and methanol (30 mL) Thionyl chloride (3 g) was addeddropwise w·ith stirring at 0C. The resulting mixture was stirred at 50C for 4 h. After cooling to room temperature the reaction was quenched by the addition of vvater/ice. The aqueousrnixture was extracted with ethyl acetate (200 mL x 2); the combined organic extracts werew·ashed vvith brine (400 mL), dried over anhydrous sodium sulfate, and concentrated undervacuum. The residue was purified by silica gel column chromatography eluting with ethyl5 acetate/petroleum ether (1: 10) to give methyl2-(4-bromo-3-fluorophenyl)acetate 153c 0. 79g, 84%) as a colorless oil.
83% With thionyl chloride; at 60℃; for 3h; To a solution of <strong>[942282-40-8]2-<strong>[942282-40-8](4-bromo-3-fluorophenyl)acetic acid</strong></strong> (500 mg, 2.146 mmol) in MeOH (10 mL, 247 mmol) was added sulfurous dichloride (0.232 mL, 3.22 mmol). The resulting mixture was stirred at 60 C. After 3 h, LCMS analysis showed the starting material had disappeared and the solvent was removed in vacuo. The residue was dissolved in DCM (60 mL) and washed with aq NaHCO3 (20 mL) and brine (20 mL). The organic layer was dried over Na2SO4, filtered and concentrated to yield a yellow oil of methyl 2-(4-bromo-3-fluorophenyl)acetate (500 mg, 1.774 mmol, 83.0% yield): 1H NMR (400 MHz, CD3OD) delta 7.53 (t, J=8.0 Hz, 1H), 7.15 (dd, J=9.8, 1.7 Hz, 1H), 7.01 (d, J=8.2 Hz, 1H), 3.75-3.61 (m, 5H); ES-LCMS m/z 248.9 (M+H).
83% With thionyl chloride; at 60℃; for 3h; To a solution of <strong>[942282-40-8]2-<strong>[942282-40-8](4-bromo-3-fluorophenyl)acetic acid</strong></strong> (500 mg, 2.146 mmol) in MeOH (10 mL, 247 mmol) was added sulfurous dichloride (0.232 mL, 3.22 mmol). The resulting mixture was stirred at 60 C. After 3 h, LCMS analysis showed the starting material had disappeared and the solvent was removed in vacuo. The residue was dissolved in DCM (60 mL) and washed with aqueous NaHC03 (20 mL) and brine (20 mL). The organic layer was dried over Na2S04, filtered and concentrated to yield a yellow oil of methyl 2-(4-bromo-3-fluorophenyl)acetate (500 mg, 1.774 mmol, 83.0% yield): lH NMR (400 MHz, CD3OD) delta 7.53 (t, J = 8.0 Hz, 1H), 7.15 (dd, J = 9.8, 1.7 Hz, 1H), 7.01 (d, J= 8.2 Hz, 1H), 3.75-3.61 (m, 5H); ES-LCMS m/z 248.9 (M+H).
1.3 g With thionyl chloride; at 20℃; for 3h;Cooling with ice; <strong>[942282-40-8]4-bromo-3-fluorophenylacetic acid</strong> (1 g, 4.3 mmol) and methanol (10 mL) were added to a 25 mL of singlemouth bottle, and thionyl chloride (0.5 mL) were added under ice bath, and reacted at room temperature for 3 hours. After reaction, the mixture was filtered and the solvent was dried with rotation under vacuum to give the product (colorless oil, 1.3 g), which was directly used in the next step. 1H NMR (400 MHz, CDCl3) delta 7.49 (t, 7=7.7 Hz, 1H), 7.08 (dd, J= 9.3, 1.8 Hz, 1H), 6.95 (dd, J= 8.2, 1.4 Hz, 1H), 3.71 (s, 3H), 3.59 (s, 2H).

  • 6
  • [ 942282-41-9 ]
  • [ 749269-74-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: caesium carbonate / N,N-dimethyl-formamide / 456 h / Inert atmosphere 2.1: water; lithium hydroxide / tetrahydrofuran / 189 h / 22 °C / Inert atmosphere 2.2: Inert atmosphere
  • 7
  • [ 942282-41-9 ]
  • C10H7BrClFO [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: caesium carbonate / N,N-dimethyl-formamide / 456 h / Inert atmosphere 2.1: water; lithium hydroxide / tetrahydrofuran / 189 h / 22 °C / Inert atmosphere 2.2: Inert atmosphere 3.1: thionyl chloride / dichloromethane / 14 h / 22 °C / Inert atmosphere
  • 8
  • [ 942282-41-9 ]
  • [ 1268444-93-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: caesium carbonate / N,N-dimethyl-formamide / 456 h / Inert atmosphere 2.1: water; lithium hydroxide / tetrahydrofuran / 189 h / 22 °C / Inert atmosphere 2.2: Inert atmosphere 3.1: thionyl chloride / dichloromethane / 14 h / 22 °C / Inert atmosphere 4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 22 °C / Inert atmosphere
  • 9
  • [ 942282-41-9 ]
  • [ 1268445-07-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: caesium carbonate / N,N-dimethyl-formamide / 456 h / Inert atmosphere 2.1: water; lithium hydroxide / tetrahydrofuran / 189 h / 22 °C / Inert atmosphere 2.2: Inert atmosphere 3.1: thionyl chloride / dichloromethane / 14 h / 22 °C / Inert atmosphere 4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 22 °C / Inert atmosphere
  • 10
  • [ 133059-43-5 ]
  • [ 942282-41-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sodium tetrahydroborate; methanol / tetrahydrofuran 2: phosphorus tribromide / dichloromethane / 20 °C 3: ethanol / 3 h / 60 °C 4: sulfuric acid; water / 16 h / 100 °C 5: thionyl chloride / 3 h / 60 °C
Multi-step reaction with 5 steps 1: sodium tetrahydroborate / methanol; tetrahydrofuran / 20 °C 2: phosphorus tribromide / dichloromethane / 20 °C 3: ethanol / 3 h / 60 °C 4: sulfuric acid; water / 16 h / 100 °C 5: thionyl chloride / 3 h / 60 °C
  • 11
  • [ 222978-01-0 ]
  • [ 942282-41-9 ]
  • 12
  • [ 127425-73-4 ]
  • [ 942282-41-9 ]
  • 14
  • [ 942282-41-9 ]
  • 2-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 16 h / 80 °C 2: ammonia / methanol / 16 h / 20 °C
Multi-step reaction with 2 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 16 h / 110 °C / Inert atmosphere 2: ammonia / methanol / 16 h / 20 °C
  • 15
  • [ 942282-41-9 ]
  • 2-(4-(6-(benzyloxy)-4-ethoxypyridin-3-yl)-3-fluorophenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 16 h / 80 °C 2: ammonia / methanol / 16 h / 20 °C 3: caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 0.25 h / 110 °C
Multi-step reaction with 3 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 16 h / 110 °C / Inert atmosphere 2: ammonia / methanol / 16 h / 20 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / 1,4-dioxane; water / 0.25 h / 110 °C
  • 16
  • [ 942282-41-9 ]
  • 2-(4-(6-(benzyloxy)-4-ethoxypyridin-3-yl)-3-fluorophenyl)-N-(4-cyano-3-(trifluoromethyl)phenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 16 h / 80 °C 2: ammonia / methanol / 16 h / 20 °C 3: caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 0.25 h / 110 °C 4: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 1 h / 120 °C
Multi-step reaction with 4 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 16 h / 110 °C / Inert atmosphere 2: ammonia / methanol / 16 h / 20 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / 1,4-dioxane; water / 0.25 h / 110 °C 4: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 1 h / 120 °C
  • 17
  • [ 942282-41-9 ]
  • N-(4-cyano-3-(trifluoromethyl)phenyl)-2-(4-(4-ethoxy-6-oxo-1,6-dihydropyridin-3-yl)-3-fluorophenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 16 h / 80 °C 2: ammonia / methanol / 16 h / 20 °C 3: caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 0.25 h / 110 °C 4: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 1 h / 120 °C 5: hydrogen; palladium on activated charcoal / methanol / 16 h / 20 °C
Multi-step reaction with 5 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 16 h / 110 °C / Inert atmosphere 2: ammonia / methanol / 16 h / 20 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / 1,4-dioxane; water / 0.25 h / 110 °C 4: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 1 h / 120 °C 5: palladium on activated charcoal; hydrogen / methanol / 16 h / 20 °C
  • 18
  • [ 942282-41-9 ]
  • [ 73183-34-3 ]
  • [ 1259022-70-2 ]
YieldReaction ConditionsOperation in experiment
81% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 110℃; for 16h; Inert atmosphere; 32.6 Methyl 2-(3-fluoro-4-(4,4,5 5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate To a mixture of methyl 2-(4-bromo-3-fluorophenyl)acetate (5 g, 20.24 mmol) in 1,4-dioxane (10 mL) was added 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (5.65 g, 22.26 mmol), KOAc (3.97 g, 40.5 mmol) and PdCl2(dppf) (1.481 g, 2.024 mmol). The resulting suspension was stirred at 110 °C for 16 h under nitrogen. The mixture was then filtered and concentrated. The crude material was purified by silica column chromatography (PE/EA = 5: 1). All fractions found to contain product by TLC (PE/EA = 5: 1, Rf = 0.6) were combined and concentrated to yield a yellow oil of methyl 2-(3-fluoro-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)acetate (6 g, 16.32 mmol, 81% yield): lH NMR (400 MHz, MeOH- 4) δ 7.66-7.58 (m, 1H), 7.07 (d, J = 7.6 Hz, 1H), 6.98 (d, J= 10.4 Hz, 1H), 3.67 (s, 5H), 1.33 (s, 12H); ES-LCMS m/z 295.1 (M+H).
63.9% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃; for 16h; 7.2 Methyl 2-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate A solution of methyl 2-(4-bromo-3-fluorophenyl)acetate (0.5 g, 2.024 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (0.617 g, 2.429 mmol), PdCl2(dppf) (0.148 g, 0.202 mmol) and potassium acetate (0.397 g, 4.05 mmol) in 1,4-dioxane (5 mL) was stirred at 80° C. for 16 h. After LCMS analysis showed the starting material had disappeared, the solvent was removed in vacuo. The residue was dissolved in EA (60 mL) and filtered. The filtrate was washed H2O (20 mL) and brine (20 mL). The organic layer was dried over Na2SO4, filtered and concentrated. The crude product was purified by column chromatography (PE/EA=5/1) to yield a yellow oil of methyl 2-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate (440 mg, 1.294 mmol, 63.9% yield): 1H NMR (400 MHz, CD3OD) δ 7.62 (t, J=7.2 Hz, 1H), 7.07 (d, J=8.4 Hz, 1H), 6.98 (d, J=10.4 Hz, 1H), 3.67 (s, 5H), 1.33 (s, 12H); ES-LCMS m/z 295.1 (M+H).
  • 19
  • [ 942282-41-9 ]
  • 2-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 16 h / 110 °C / Inert atmosphere 2: lithium hydroxide monohydrate; water / tetrahydrofuran / 16 h / 25 °C
  • 20
  • [ 942282-41-9 ]
  • N-(4-(3-((tert-butyldimethylsilyl)oxy)-2,2-dimethylpropyl)-3-(trifluoromethyl)phenyl)-2-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 16 h / 110 °C / Inert atmosphere 2: lithium hydroxide monohydrate; water / tetrahydrofuran / 16 h / 25 °C 3: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 25 °C
  • 21
  • [ 942282-41-9 ]
  • 2-(4-(6-(benzyloxy)-4-ethoxypyridin-3-yl)-3-fluorophenyl)-N-(4-(3-((tert-butyldimethylsilyl)oxy)-2,2-dimethylpropyl)-3-(trifluoromethyl)phenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 16 h / 110 °C / Inert atmosphere 2: lithium hydroxide monohydrate; water / tetrahydrofuran / 16 h / 25 °C 3: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 25 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / 1,4-dioxane; water / 16 h / 110 °C / Inert atmosphere
  • 22
  • [ 942282-41-9 ]
  • 2-(4-(6-(benzyloxy)-4-ethoxypyridin-3-yl)-3-fluorophenyl)-N-(4-(3-hydroxy-2,2-dimethylpropyl)-3-(trifluoromethyl)phenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 16 h / 110 °C / Inert atmosphere 2: lithium hydroxide monohydrate; water / tetrahydrofuran / 16 h / 25 °C 3: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 25 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / 1,4-dioxane; water / 16 h / 110 °C / Inert atmosphere 5: trifluoroacetic acid / dichloromethane / 2 h / 25 °C
  • 23
  • [ 942282-41-9 ]
  • 2-(4-(4-ethoxy-6-oxo-1,6-dihydropyridin-3-yl)-3-fluorophenyl)-N-(4-(3-hydroxy-2,2-dimethylpropyl)-3-(trifluoromethyl)phenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 16 h / 110 °C / Inert atmosphere 2: lithium hydroxide monohydrate; water / tetrahydrofuran / 16 h / 25 °C 3: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 25 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / 1,4-dioxane; water / 16 h / 110 °C / Inert atmosphere 5: trifluoroacetic acid / dichloromethane / 2 h / 25 °C 6: palladium on activated charcoal; hydrogen / methanol / 16 h / 25 °C
  • 24
  • [ 942282-41-9 ]
  • [ 74-88-4 ]
  • methyl 2-(4-bromo-3-fluorophenyl)-2-methylpropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: methyl 2-(4-bromo-3-fluorophenyl)acetate With sodium hydride In mineral oil at 60℃; for 1h; Inert atmosphere; Stage #2: methyl iodide In mineral oil at 60℃; for 2h; 17A Methyl 2-(4-bromo-3-fluorophenyl)-2-methylpropanoate Example 17A Methyl 2-(4-bromo-3-fluorophenyl)-2-methylpropanoate Under argon and at RT, 186.2 mg (4.66 mmol) of sodium hydride (60% in mineral oil) were added to 500 mg (2.02 mmol) of methyl (4-bromo-3-fluorophenyl)acetate. After stirring at 60° C. for one hour, 631.94 mg (4.45 mmol) of iodomethane were slowly added dropwise. The mixture was then stirred at 60° C. for 2 h. The reaction mixture was concentrated and diluted with ethyl acetate and washed with water and saturated sodium chloride solution. The organic phase was separated off, dried over sodium sulphate and filtered, and the filtrate was concentrated. This gave 633 mg (69% of theory, purity: 69%) of an oil, which was reacted further without further purification. GC-MS [Methode 5]: Rt=4.92 min; MS (ESIneg): m/z=274 (M-H)-
  • 25
  • [ 942282-41-9 ]
  • diphenyl(vinyl)sulfonium trifluoromethanesulfonate [ No CAS ]
  • methyl 1-(4-bromo-3-fluoro-phenyl)cyclopropanecarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 21℃; for 12h; General Procedure A: for aryl / heteroaryl acetates substrate’s cyclopropanation General procedure: To a 5 mL Schlenk tube were added aryl / heteroaryl acetates 3 (1.0 mmol, 1.0 equiv.), vinyl diphenylsulfonium triflate (434.4 mg, 1.2 mmol, 1.2 equiv.) and DMSO (5 mL). The mixture was stirred at room temperature for 2 min and to the mixture was added DBU (456 mg, 3 mmol, 3.0 equiv.). The mixture was stirred for 12 hours at room temperature till the reaction was complete. To the resulting mixture was added saturated ammonium chloride solution (25 mL), and the mixture was then extracted with EtOAc (3 x 150 mL). The combined organic layers were washed with H2O (2 x 30 mL), dried with anhydrous sodium sulfate. After concentration, product 4 was purified using column chromatography on silica gel using an appropriate eluent.
  • 26
  • [ 942282-41-9 ]
  • 2-{4-[(1S,4S,5R)-5-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy}-2-azabicyclo[2.2.1]heptan-2-yl]-3-fluorophenyl}acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: caesium carbonate; chloro(2-dicyclohexylphosphino-2‘,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl)]palladium(II) / toluene / 110 °C / Inert atmosphere; Sealed tube 2: water; lithium hydroxide / methanol / 40 °C
  • 27
  • [ 942282-41-9 ]
  • (1S,4S,5R)-5-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-2-azabicyclo[2.2.1]heptane hydroiodide salt [ No CAS ]
  • methyl 2-[4-[(1S,4S,5R)-5-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]-2-azabicyclo[2.2.1]heptan-2-yl]-3-fluorophenyl]acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
14% With chloro(2-dicyclohexylphosphino-2‘,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl)]palladium(II); caesium carbonate In toluene at 110℃; Inert atmosphere; Sealed tube; 146.3 Step 3. To a 5 mL sealed tube purged with and maintained under an inert atmosphere ofnitrogen was added a solution of methyl 2-(4-bromo-3-fluorophenyl)acetate 153c (260 mg,10 1.0.5 mmoL 2.66 equiv.) in toluene (3 mL), (1S,4S,5R)-5-[[.5-cyclopropyl-3-(2,6-dichlorophenyl)- L2-oxazol-4-yl]methoxy]-2-azabicydo[2.2.l]heptane hydroiodide salt 12dd(200 mg, 0.3943 mmoL 1.00 equiv), Cs2C03 (345 mg, 1.06 mmol, 2.69 equiv), and Ru-phosprecatalyst(89 9 mg, 0.11 mmol, 0.28 equiv). The resulting mixture vvas stirred at 110 °Covernight. The reaction mixture '.Vas cooled to room temperature, and added with 10 mL of15 water. The aqueous mixture was extracted with ethyl acetate (50 mL x 2). The combinedorganic extracts were washed with brine (50 mL x 2), dried over anhydrous sodium sulfateand concentrated under vacuum The residue was purified by silica gel columnchromatography eluting with ethyl acetate/petroleum ether (l :2) to yield methyl 2-[4-[ (1S,4S,5R)-5-[ [ 5-cyclopropyl-3-(2,6-dichlorophenyl)-1 ,2-oxazol-4-yllmethoxy ]-2-20 azabicyclo[ 2.2.l]heptan-2-y l]-3-iluoropheny l]acetate 153d (30 mg, 14%) as yellow oil.
  • 28
  • [ 942282-41-9 ]
  • tert-butyl N-[(3S)-1-[3-(4-cyano-3-fluorophenyl)-4-[2-fluoro-4-(2-hydroxy-2-methylpropyl)phenyl]benzoyl]pyrrolidin-3-yl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 0.5 h / 120 °C / Microwave irradiation
Multi-step reaction with 2 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; 1,4-dioxane / 0.5 h / 120 °C / Microwave irradiation
Multi-step reaction with 2 steps 1: tetrahydrofuran / -30 - 20 °C 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 0.5 h / 120 °C / Microwave irradiation
Multi-step reaction with 2 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; tetrahydrofuran / 0.5 h / 120 °C / Microwave irradiation

  • 29
  • [ 942282-41-9 ]
  • tert-butyl N-[(3-exo)-8-[3-(4-cyano-3-fluorophenyl)-4-[2-fluoro-4-(2-hydroxy-2-methylpropyl)phenyl]benzoyl]-8-azabicyclo[3.2.1]octan-3-yl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 0.75 h / 125 °C
Multi-step reaction with 2 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; 1,4-dioxane / 0.75 h / 125 °C
Multi-step reaction with 2 steps 1: tetrahydrofuran / -30 - 20 °C 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 0.75 h / 125 °C
Multi-step reaction with 2 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 0.75 h / 125 °C

  • 30
  • [ 942282-41-9 ]
  • 4-[5-[(3-exo)-3-amino-8-azabicyclo[3.2.1]octane-8-carbonyl]-2-[2-fluoro-4-(2-hydroxy-2-methylpropyl)phenyl]phenyl]-2-fluorobenzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 0.75 h / 125 °C 3: trifluoroacetic acid
Multi-step reaction with 3 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; 1,4-dioxane / 0.75 h / 125 °C 3: trifluoroacetic acid
Multi-step reaction with 3 steps 1: tetrahydrofuran / -30 - 20 °C 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 0.75 h / 125 °C 3: trifluoroacetic acid
Multi-step reaction with 3 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 0.75 h / 125 °C 3: trifluoroacetic acid

  • 31
  • [ 942282-41-9 ]
  • 4-[5-[(3S)-3-aminopyrrolidine-1-carbonyl]-2-[2-fluoro-4-(2-hydroxy-2-methyl-propyl)phenyl]phenyl]-2-fluoro-benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 0.5 h / 120 °C / Microwave irradiation 3: hydrogenchloride / water; methanol / 0.5 h / 20 °C
Multi-step reaction with 3 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; 1,4-dioxane / 0.5 h / 120 °C / Microwave irradiation 3: hydrogenchloride / water; methanol / 0.5 h / 20 °C
Multi-step reaction with 3 steps 1: tetrahydrofuran / -30 - 20 °C 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 0.5 h / 120 °C / Microwave irradiation 3: hydrogenchloride / water; methanol / 0.5 h / 20 °C
Multi-step reaction with 3 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; tetrahydrofuran / 0.5 h / 120 °C / Microwave irradiation 3: hydrogenchloride / methanol / 0.5 h / 20 °C

  • 32
  • [ 942282-41-9 ]
  • tert-butyl-N-[(3-endo)-8-[3-(4-cyano-3-fluorophenyl)-4-[2-fluoro-4-(2-hydroxy-2-methyl-propyl)phenyl]benzoyl]-8-azabicyclo[3.2.1]octan-3-yl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 0.5 h / 120 °C
Multi-step reaction with 2 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; 1,4-dioxane / 0.5 h / 120 °C / Microwave irradiation
Multi-step reaction with 2 steps 1: tetrahydrofuran / -30 - 20 °C 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 0.5 h / 120 °C / Microwave irradiation
Multi-step reaction with 2 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 0.5 h / 120 °C / Microwave irradiation

  • 33
  • [ 942282-41-9 ]
  • 4-[5-[(3-endo)-3-amino-8-azabicyclo[3.2.1]octane-8-carbonyl]-2-[2-fluoro-4-(2-hydroxy-2-methylpropyl)phenyl]phenyl]-2-fluorobenzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 0.5 h / 120 °C 3: hydrogenchloride / water; methanol / 0.5 h / 20 °C
Multi-step reaction with 3 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; 1,4-dioxane / 0.5 h / 120 °C / Microwave irradiation 3: hydrogenchloride / water; methanol / 0.5 h / 20 °C
Multi-step reaction with 3 steps 1: tetrahydrofuran / -30 - 20 °C 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 0.5 h / 120 °C / Microwave irradiation 3: hydrogenchloride / water; methanol / 0.5 h / 20 °C
Multi-step reaction with 3 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 0.5 h / 120 °C / Microwave irradiation 3: hydrogenchloride / water; methanol / 0.5 h / 20 °C

  • 34
  • [ 942282-41-9 ]
  • tert-butyl 3-(4-cyano-3-fluoro-phenyl)-4-[2-fluoro-4-(2-hydroxy-2-methyl-propyl)phenyl]benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: XPhos; bis(dibenzylideneacetone)-palladium(0); potassium phosphate / 1,4-dioxane / 100 °C
Multi-step reaction with 2 steps 1: tetrahydrofuran / -30 - 20 °C 2: XPhos; bis(dibenzylideneacetone)-palladium(0); potassium phosphate / 1,4-dioxane / 100 °C
Multi-step reaction with 2 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: potassium phosphate; bis(dibenzylideneacetone)-palladium(0); XPhos / 1,4-dioxane / 100 °C
  • 35
  • [ 942282-41-9 ]
  • 3-(4-cyano-3-fluoro-phenyl)-4-[2-fluoro-4-(2-hydroxy-2-methyl-propyl)phenyl]benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: XPhos; bis(dibenzylideneacetone)-palladium(0); potassium phosphate / 1,4-dioxane / 100 °C 3: hydrogenchloride / water; tetrahydrofuran / 2 h / 0 - 20 °C
Multi-step reaction with 3 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: XPhos; bis(dibenzylideneacetone)-palladium(0); potassium phosphate / 1,4-dioxane / 100 °C 3: hydrogenchloride / water; tetrahydrofuran / 2 h / 0 - 20 °C
Multi-step reaction with 3 steps 1: tetrahydrofuran / -30 - 20 °C 2: XPhos; bis(dibenzylideneacetone)-palladium(0); potassium phosphate / 1,4-dioxane / 100 °C 3: hydrogenchloride / water; tetrahydrofuran / 2 h / 0 - 20 °C
Multi-step reaction with 3 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: potassium phosphate; bis(dibenzylideneacetone)-palladium(0); XPhos / 1,4-dioxane / 100 °C 3: hydrogenchloride / tetrahydrofuran / 2 h / 0 - 20 °C

  • 36
  • [ 942282-41-9 ]
  • N-[(1S,3R,4R)-rel-7-[3-(4-cyano-3-fluorophenyl)-4-[2-fluoro-4-(2-hydroxy-2-methylpropyl)phenyl]benzoyl]-7-azabicyclo[2.2.1]heptan-3-yl]-2,4-dinitrobenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: XPhos; bis(dibenzylideneacetone)-palladium(0); potassium phosphate / 1,4-dioxane / 100 °C 3: hydrogenchloride / water; tetrahydrofuran / 2 h / 0 - 20 °C 4: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / tetrahydrofuran / 1 h / 50 °C
Multi-step reaction with 4 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: XPhos; bis(dibenzylideneacetone)-palladium(0); potassium phosphate / 1,4-dioxane / 100 °C 3: hydrogenchloride / water; tetrahydrofuran / 2 h / 0 - 20 °C 4: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / tetrahydrofuran / 1 h / 50 °C
Multi-step reaction with 4 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: potassium phosphate; bis(dibenzylideneacetone)-palladium(0); XPhos / 1,4-dioxane / 100 °C 3: hydrogenchloride / tetrahydrofuran / 2 h / 0 - 20 °C 4: HATU; triethylamine / tetrahydrofuran / 1 h / 50 °C
  • 37
  • [ 942282-41-9 ]
  • tert-butyl N-[3-[3-(4-cyano-3-fluorophenyl)-4-[2-fluoro-4-(2-hydroxy-2-methylpropyl)phenyl]benzoyl]-3-azabicyclo[2.2.1]heptan-7-yl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: XPhos; bis(dibenzylideneacetone)-palladium(0); potassium phosphate / 1,4-dioxane / 100 °C 3: hydrogenchloride / water; tetrahydrofuran / 2 h / 0 - 20 °C 4: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / tetrahydrofuran / 3 h / 50 °C
Multi-step reaction with 4 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: XPhos; bis(dibenzylideneacetone)-palladium(0); potassium phosphate / 1,4-dioxane / 100 °C 3: hydrogenchloride / water; tetrahydrofuran / 2 h / 0 - 20 °C 4: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / tetrahydrofuran / 3 h / 50 °C
Multi-step reaction with 4 steps 1: tetrahydrofuran / -30 - 20 °C 2: XPhos; bis(dibenzylideneacetone)-palladium(0); potassium phosphate / 1,4-dioxane / 100 °C 3: hydrogenchloride / water; tetrahydrofuran / 2 h / 0 - 20 °C 4: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / tetrahydrofuran / 3 h / 50 °C
Multi-step reaction with 4 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: potassium phosphate; bis(dibenzylideneacetone)-palladium(0); XPhos / 1,4-dioxane / 100 °C 3: hydrogenchloride / tetrahydrofuran / 2 h / 0 - 20 °C 4: HATU; triethylamine / tetrahydrofuran / 3 h / 50 °C

  • 38
  • [ 942282-41-9 ]
  • 5’-(7-amino-2-azabicyclo[2.2.1]heptane-2-carbonyl)-2",3-difluoro-4"-(2-hydroxy-2-methylpropyl)-[1,1’:2’,1"-terphenyl]-4-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: XPhos; bis(dibenzylideneacetone)-palladium(0); potassium phosphate / 1,4-dioxane / 100 °C 3: hydrogenchloride / water; tetrahydrofuran / 2 h / 0 - 20 °C 4: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / tetrahydrofuran / 3 h / 50 °C 5: hydrogenchloride / water; methanol / 0.5 h / 20 °C
Multi-step reaction with 5 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: XPhos; bis(dibenzylideneacetone)-palladium(0); potassium phosphate / 1,4-dioxane / 100 °C 3: hydrogenchloride / water; tetrahydrofuran / 2 h / 0 - 20 °C 4: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / tetrahydrofuran / 3 h / 50 °C 5: hydrogenchloride / water; methanol / 0.5 h / 20 °C
Multi-step reaction with 5 steps 1: tetrahydrofuran / -30 - 20 °C 2: XPhos; bis(dibenzylideneacetone)-palladium(0); potassium phosphate / 1,4-dioxane / 100 °C 3: hydrogenchloride / water; tetrahydrofuran / 2 h / 0 - 20 °C 4: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / tetrahydrofuran / 3 h / 50 °C 5: hydrogenchloride / water; methanol / 0.5 h / 20 °C
Multi-step reaction with 5 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: potassium phosphate; bis(dibenzylideneacetone)-palladium(0); XPhos / 1,4-dioxane / 100 °C 3: hydrogenchloride / tetrahydrofuran / 2 h / 0 - 20 °C 4: HATU; triethylamine / tetrahydrofuran / 3 h / 50 °C 5: hydrogenchloride / methanol / 0.5 h / 20 °C

  • 39
  • [ 942282-41-9 ]
  • N-[(1S,3S,4R)-rel-7-[3-(4-cyano-3-fluoro-phenyl)-4-[2-fluoro-4-(2-hydroxy-2-methylpropyl)phenyl]benzoyl]-7-azabicyclo[2.2.1]heptan-3-yl]-2,4-dinitrobenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: XPhos; bis(dibenzylideneacetone)-palladium(0); potassium phosphate / 1,4-dioxane / 100 °C 3: hydrogenchloride / water; tetrahydrofuran / 2 h / 0 - 20 °C 4: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / tetrahydrofuran / 1 h / 50 °C
Multi-step reaction with 4 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: XPhos; bis(dibenzylideneacetone)-palladium(0); potassium phosphate / 1,4-dioxane / 100 °C 3: hydrogenchloride / water; tetrahydrofuran / 2 h / 0 - 20 °C 4: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / tetrahydrofuran / 1 h / 50 °C
Multi-step reaction with 4 steps 1: tetrahydrofuran / -30 - 20 °C 2: XPhos; bis(dibenzylideneacetone)-palladium(0); potassium phosphate / 1,4-dioxane / 100 °C 3: hydrogenchloride / water; tetrahydrofuran / 2 h / 0 - 20 °C 4: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / tetrahydrofuran / 1 h / 50 °C
Multi-step reaction with 4 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: potassium phosphate; bis(dibenzylideneacetone)-palladium(0); XPhos / 1,4-dioxane / 100 °C 3: hydrogenchloride / tetrahydrofuran / 2 h / 0 - 20 °C 4: HATU; triethylamine / tetrahydrofuran / 1 h / 50 °C

  • 40
  • [ 942282-41-9 ]
  • 5’-((1S,2S,4R)-rel-2-amino-7-azabicyclo[2.2.1]heptane-7-carbonyl)-2",3-difluoro-4"-(2-hydroxy-2-methylpropyl)-[1,1’:2’,1"-terphenyl]-4-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: XPhos; bis(dibenzylideneacetone)-palladium(0); potassium phosphate / 1,4-dioxane / 100 °C 3: hydrogenchloride / water; tetrahydrofuran / 2 h / 0 - 20 °C 4: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / tetrahydrofuran / 1 h / 50 °C 5: triethylamine; mercaptoacetic acid / dichloromethane / 2 h / 0 - 20 °C
Multi-step reaction with 5 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: XPhos; bis(dibenzylideneacetone)-palladium(0); potassium phosphate / 1,4-dioxane / 100 °C 3: hydrogenchloride / water; tetrahydrofuran / 2 h / 0 - 20 °C 4: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / tetrahydrofuran / 1 h / 50 °C 5: triethylamine; mercaptoacetic acid / dichloromethane / 2 h / 0 - 20 °C
Multi-step reaction with 5 steps 1: tetrahydrofuran / -30 - 20 °C 2: XPhos; bis(dibenzylideneacetone)-palladium(0); potassium phosphate / 1,4-dioxane / 100 °C 3: hydrogenchloride / water; tetrahydrofuran / 2 h / 0 - 20 °C 4: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / tetrahydrofuran / 1 h / 50 °C 5: triethylamine; mercaptoacetic acid / dichloromethane / 2 h / 0 - 20 °C
Multi-step reaction with 5 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: potassium phosphate; bis(dibenzylideneacetone)-palladium(0); XPhos / 1,4-dioxane / 100 °C 3: hydrogenchloride / tetrahydrofuran / 2 h / 0 - 20 °C 4: HATU; triethylamine / tetrahydrofuran / 1 h / 50 °C 5: triethylamine; mercaptoacetic acid / dichloromethane / 2 h / 0 - 20 °C

  • 41
  • [ 942282-41-9 ]
  • [ 75-16-1 ]
  • 1-(4-bromo-3-fluorophenyl)-2-methylpropan-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; diethyl ether at -30 - 20℃; 28.1 Step 1 methyl 2-(4-bromo-3-fluorophenyl)acetate (500 mg) was dissolved in THF (2.2 mL). At -30°C, a solution of 3M MeMgBr in ether (5.40 mL) was added thereto dropwise, followed by stirring at room temperature overnight. Thereaction solution was introduced into an aqueous ammonium chloride solution, ethyl acetate was added thereto, andthe mixture was washed sequentially with water and saturated brine. After the organic layer was dried over anhydroussodium sulfate, the solvent was distilled off. The residue was purified by silica gel column chromatography (mobile phase:hexane/ethyl acetate = 10% → 50%) to give 1-(4-bromo-3-fluorophenyl)-2-methylpropan-2-ol.
In tetrahydrofuran; diethyl ether at -30 - 20℃; 28.1; 290.1 Step 1 Methyl 2-(4-bromo-3-fluoro-phenyl)acetate (500 mg) was dissolved in THF (2.2 mL). At -30°C, a solution of 3 M MeMgBr in diethyl ether (5.40 mL) was added thereto dropwise, followed by stirring at room temperature overnight. The reaction mixture was introduced into an aqueous ammonium chloride solution, ethyl acetate was added thereto, and the mixture was washed sequentially with water and saturated brine. After the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off. The residue was purified by silica gel column chromatography (mobile phase: ethyl acetate/hexane = 10% → 50%) to give 1-(4-bromo-3-fluoro-phenyl)-2-methyl-propan-2-ol.
In tetrahydrofuran; diethyl ether at -30 - 20℃; 28.1; 290.1 Step 1 Methyl 2-(4-bromo-3-fluoro-phenyl)acetate (500 mg) was dissolved in THF (2.2 mL). At -30°C, a solution of 3M MeMgBr in ether (5.40 mL) was added thereto dropwise, followed by stirring at room temperature overnight. Thereaction mixture was introduced into an aqueous ammonium chloride solution, ethyl acetate was added thereto, and themixture was washed sequentially with water and saturated brine. After the organic layer was dried over anhydroussodium sulfate, the solvent was distilled off. The residue was purified by silica gel column chromatography (mobile phase:ethyl acetate/hexane = 10% → 50%) to give 1-(4-bromo-3-fluoro-phenyl)-2-methyl-propan-2-ol.
In tetrahydrofuran at -30 - 20℃; 28.1 Step 1 Step 1 Methyl 2-(4-bromo-3-fluoro-phenyl)acetate (500 mg) was dissolved in THF (2.2 mL). At -30°C, a solution of 3 M MeMgBr in ether (5.40 mL) was added thereto dropwise, followed by stirring at room temperature overnight. The reaction mixture was introduced into an aqueous ammonium chloride solution, ethyl acetate was added thereto, and the mixture was washed sequentially with water and saturated brine. After the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off. The residue was purified by silica gel column chromatography (mobile phase: ethyl acetate/hexane = 10% → 50%) to give 1-(4-bromo-3-fluoro-phenyl)-2-methyl-propan-2-ol.

  • 42
  • [ 942282-41-9 ]
  • [ 925-90-6 ]
  • 1-[(4-bromo-3-fluorophenyl)methyl]cyclopropanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With titanium(IV) isopropylate In tetrahydrofuran; diethyl ether at 0 - 20℃; 67.1 Step 1 methyl-2-(4-bromo-3-fluorophenyl)acetate (500 mg) and titanium isopropoxide (0.84 mL) were dissolved inTHF (5 mL). At 0°C, a solution of 3 M EtMgBr in diethyl ether (1.9 mL) was added thereto dropwise, followed by stirringat room temperature overnight. Ethyl acetate was added thereto, the mixture was washed sequentially with water andsaturated brine, and dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was purified bysilica gel column chromatography (mobile phase: hexane/ethyl acetate) to give 1-[(4-bromo-3-fluorophenyl)methyl]cyclopropanol.
With titanium(IV) isopropylate In tetrahydrofuran; diethyl ether at 0 - 20℃; 67.1 Step 1 Methyl-2-(4-bromo-3-fluoro-phenyl)acetate (500 mg) and titanium isopropoxide (0.84 mL) were dissolved in THF (5 mL). At 0°C, a solution of 3 M EtMgBr in diethyl ether (1.9 mL) was added thereto dropwise, followed by stirring at room temperature overnight. Ethyl acetate was added thereto, the mixture was washed sequentially with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography (mobile phase: hexane/ethyl acetate) to give 1-[(4-bromo-3-fluoro-phenyl)methyl]cyclopropanol.
With titanium(IV)isopropoxide In tetrahydrofuran; diethyl ether at 0 - 20℃; 67.1 Step 1 Methyl-2-(4-bromo-3-fluoro-phenyl)acetate (500 mg) and titanium isopropoxide (0.84 mL) were dissolved inTHF (5 mL). At 0°C, a solution of 3 M EtMgBr in diethyl ether (1.9 mL) was added thereto dropwise, followed by stirringat room temperature overnight. Ethyl acetate was added thereto, the mixture was washed sequentially with water andsaturated brine, and dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was purified bysilica gel column chromatography (mobile phase: hexane/ethyl acetate) to give 1-[(4-bromo-3-fluoro-phenyl)methyl]cyclopropanol.
With titanium(IV) isopropylate In tetrahydrofuran; diethyl ether at 0 - 20℃; 67.1 Step 1 Step 1 Methyl-2-(4-bromo-3-fluoro-phenyl)acetate (500 mg) and titanium isopropoxide (0.84 mL) were dissolved in THF (5 mL). At 0°C, a solution of 3 M EtMgBr in diethyl ether (1.9 mL) was added thereto dropwise, followed by stirring at room temperature overnight. Ethyl acetate was added thereto, the mixture was washed sequentially with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography (mobile phase: hexane/ethyl acetate) to give 1-[(4-bromo-3-fluoro-phenyl)methyl]cyclopropanol.

  • 43
  • [ 942282-41-9 ]
  • (4-(3-(5-cyclopropyl-2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-6-yl)-2-oxooxazolidin-4-yl)-2-fluorophenyl)boronic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 4 h / Reflux 2: N,N-dimethyl-formamide / 18 h / 85 °C 3: lithium borohydride / tetrahydrofuran / 2 h / 0 - 20 °C 4: triethylamine / dichloromethane / 19 h / 0 - 20 °C 5: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / 1,4-dioxane / 18 h / 100 °C / Inert atmosphere 6: hydrogenchloride / water; tetrahydrofuran / 18 h / 20 °C
  • 45
  • [ 557-21-1 ]
  • [ 942282-41-9 ]
  • [ 444807-50-5 ]
YieldReaction ConditionsOperation in experiment
60.2% With tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 155℃; for 1.5h;Inert atmosphere; Microwave irradiation; Ethyl-4-bromo-3-fluorophenylacetate (1.3 g, 5.3 mmol), zinc cyanide (924 mg, 7.89 mmol) and N,N-dimethylformamide (10 mL) were added to a 20 mL microwave tube. The mixture was nitrogen sparged for 5 min, tetrakis(triphenylphosphine)palladium (613 mg, 0.53 mmol) was added, and the mixture was stirred and heated to 155 C for 1.5 hours under microwave. After completion of reaction, the mixture was cooled to room temperature, and extracted with ethyl acetate for three times, and the organic layers were combined, washed 5 times with water, and finally washed with saturated sodium chloride, and the organic layer was concentrated in vacuo to get a crude product. Then the crude product was separated by a silica gel column (petroleum ether: ethyl acetate = 8:1-5:1) to give the product (while solid, 620 mg), with a yield of 60.2%. 1H NMR(400 MHz, CDCl3) 7.58 (t, J= 7.2 Hz, 1H), 7.18 (d, J= 8.7 Hz, 2H), 3.72 (s, 3H), 3.69 (s, 2H). MS (ESI) m/z: 194.1(MH+)
With tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 155℃; for 1.5h;Microwave irradiation; Inert atmosphere; General procedure: Methyl 4-bromo aryl substituted carboxylic ester 21(4.1 mmol, 1 eq), zinc cyanide (6.1 mmol, 1.5 eq) and N, N-dimethylformamide(10 mL) were added to a microwave tube. Themixture was nitrogen sparged for 5 min, then tetrakis(-triphenylphosphine)palladium (0.2 mmol, 0.05 eq) was added, andthe mixture was stirred and heated to 155 C for 1.5 h under microwave.After completion of reaction, the mixture was cooled toroom temperature, and extracted with ethyl acetate for three times.The organic layers were combined, washed 5 times with water,finallywashed with saturated sodium chloride, and concentrated invacuo to get a crude product. The crude product was separated by asilica gel column to give the product methyl 4-cyano arylsubstituted carboxylic ester (22).
  • 46
  • [ 942282-41-9 ]
  • [ 444807-55-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 1.5 h / 155 °C / Inert atmosphere; Microwave irradiation 2: hydrogen / methanol / 2 h
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 1.5 h / 155 °C / Microwave irradiation; Inert atmosphere 2: nickel; ammonium hydroxide; hydrogen / methanol / 20 °C
  • 47
  • [ 942282-41-9 ]
  • C24H18Cl2F4N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 1.5 h / 155 °C / Inert atmosphere; Microwave irradiation 2.1: hydrogen / methanol / 2 h 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.08 h / Cooling with ice 3.2: 0.17 h / Cooling with ice 3.3: 0.5 h / Cooling with ice
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 1.5 h / 155 °C / Microwave irradiation; Inert atmosphere 2.1: nickel; ammonium hydroxide; hydrogen / methanol / 20 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C 3.2: 0.5 h / 20 °C
  • 48
  • [ 942282-41-9 ]
  • 2-(4-((3-(2,6-dichloro-2’-(trifluoromethoxy)-[1,1'-biphenyl]-4-yl)ureido)methyl)-3-fluorophenyl)acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 1.5 h / 155 °C / Inert atmosphere; Microwave irradiation 2.1: hydrogen / methanol / 2 h 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.08 h / Cooling with ice 3.2: 0.17 h / Cooling with ice 3.3: 0.5 h / Cooling with ice 4.1: water / ethanol / 2 h / 20 °C
Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 1.5 h / 155 °C / Microwave irradiation; Inert atmosphere 2.1: nickel; ammonium hydroxide; hydrogen / methanol / 20 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C 3.2: 0.5 h / 20 °C 4.1: sodium hydroxide / water; ethanol / 20 °C
  • 49
  • [ 942282-41-9 ]
  • 5’-((1R,2S,4S)-rel-2-amino-7-azabicyclo[2.2.1]heptane-7-carbonyl)-2",3-difluoro-4"-(2-hydroxy-2-methylpropyl)-[1,1’:2’,1"-terphenyl]-4-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: XPhos; bis(dibenzylideneacetone)-palladium(0); potassium phosphate / 1,4-dioxane / 100 °C 3: hydrogenchloride / water; tetrahydrofuran / 2 h / 0 - 20 °C 4: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / tetrahydrofuran / 1 h / 50 °C 5: triethylamine; mercaptoacetic acid / dichloromethane / 2 h / 0 - 20 °C
Multi-step reaction with 5 steps 1: tetrahydrofuran / -30 - 20 °C 2: XPhos; bis(dibenzylideneacetone)-palladium(0); potassium phosphate / 1,4-dioxane / 100 °C 3: hydrogenchloride / water; tetrahydrofuran / 2 h / 0 - 20 °C 4: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / tetrahydrofuran / 1 h / 50 °C 5: triethylamine; mercaptoacetic acid / dichloromethane / 2 h / 0 - 20 °C
Multi-step reaction with 5 steps 1: tetrahydrofuran; diethyl ether / -30 - 20 °C 2: potassium phosphate; bis(dibenzylideneacetone)-palladium(0); XPhos / 1,4-dioxane / 100 °C 3: hydrogenchloride / tetrahydrofuran / 2 h / 0 - 20 °C 4: HATU; triethylamine / tetrahydrofuran / 1 h / 50 °C 5: triethylamine; mercaptoacetic acid / dichloromethane / 1 h / 0 - 20 °C
  • 50
  • [ 942282-41-9 ]
  • [ 1331944-00-3 ]
YieldReaction ConditionsOperation in experiment
77.8% With lithium tetrahydridoborate In tetrahydrofuran at 20℃; for 2h;
With sodium tetrahydridoborate In tetrahydrofuran; methanol Reflux;
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