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[ CAS No. 1060816-22-9 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1060816-22-9
Chemical Structure| 1060816-22-9
Chemical Structure| 1060816-22-9
Structure of 1060816-22-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1060816-22-9 ]

CAS No. :1060816-22-9 MDL No. :MFCD09743496
Formula : C6H6BrNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :VZYKDUOPMKESLS-UHFFFAOYSA-N
M.W : 220.02 Pubchem ID :37818738
Synonyms :

Calculated chemistry of [ 1060816-22-9 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.33
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 40.29
TPSA : 52.33 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) : -6.29 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.16
Log Po/w (XLOGP3) : 1.91
Log Po/w (WLOGP) : 1.61
Log Po/w (MLOGP) : 0.36
Log Po/w (SILICOS-IT) : 1.65
Consensus Log Po/w : 1.54

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.55
Solubility : 0.626 mg/ml ; 0.00285 mol/l
Class : Soluble
Log S (Ali) : -2.63
Solubility : 0.513 mg/ml ; 0.00233 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.58
Solubility : 0.58 mg/ml ; 0.00264 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.42

Safety of [ 1060816-22-9 ]

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 [ 1060816-22-9 ]

* 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 [ 1060816-22-9 ]

[ 1060816-22-9 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 1060816-22-9 ]
  • [ 139301-27-2 ]
  • [ 1258269-01-0 ]
  • 2
  • [ 1060816-22-9 ]
  • [ 3900-89-8 ]
  • ethyl 2-(2-chlorophenyl)-1,3-oxazole-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); DavePhos; In toluene; at 110℃; for 20h;Inert atmosphere; Example 44A Ethyl 2-(2-chlorophenyl)-1,3-oxazole-5-carboxylate Under argon, 300 mg (1.71 mmol) of <strong>[1060816-22-9]ethyl 2-bromo-1,3-oxazole-5-carboxylate</strong> together with 422 mg (2.56 mmol) of 2-chlorophenylboronic acid were dissolved in 7 ml of toluene, and 67 mg (0.17 mmol) of 2-dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl, 78 mg (0.085 mmol) of tris(dibenzylideneacetone)dipalladium and 725 mg (3.42 mmol) of potassium phosphate were added successively. The mixture was heated to 110 C. and stirred at this temperature for 20 h. For work-up, the reaction mixture was allowed to cool to RT and diluted with 20 ml of ethyl acetate and 20 ml of water. After phase separation, the aqueous phase was extracted two more times with in each case 20 ml of ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by preparative HPLC [Method 19]. This gave 217 mg (50% of theory) of the target compound. LC/MS [Method 3]: Rt=1.21 min; MS [ESIpos]: m/z=252 (M+H)+.
  • 3
  • [ 1060816-22-9 ]
  • 4-(tributylstannanyl)pyridazine [ No CAS ]
  • C10H9N3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); cesium fluoride; In N,N-dimethyl-formamide; at 80℃; for 0.5h;Inert atmosphere; Microwave irradiation; i) A mixture of <strong>[1060816-22-9]ethyl 2-bromooxazole-5-carboxylate</strong> (0.750 g, 3.41 mmol), CsF (1.55 g, 10.2 mmol) and 4- (tributylstannyl)pyridazine (1.32 g, 3.58 mmol) was dissolved in DMF (15 mL). Tetrakis(triphenylphosphine)palladium(0) (0.315 g, 0.273 mmol) and Cul (0.085 g, 0.44 mmol) were added and the RM was degassed with Ar. The mixture was stirred in the microwave at 80C for 30 mm. The RM was diluted with EtOAc (50 mL) and an aqueous saturated solution of KF (50 mL) and stirred for 16 h. The mixture was filtered; the aqueous layer was extracted with EtOAc. The combined organic layer was washed with an aqueous saturated solution of NaHCO3 (100 mL), water (2x 100 mL) and brine (100 mL). The organiclayer was dried over Na2SO4 and concentrated in vacuo. FC (EtOAc/heptane 1:9 -> 1:0) afforded INT21A (0.349 g, 1.59 mmol, 47%) as a white solid. LCMS: caic. for [M+H]=220.06, found 220.2.
  • 4
  • [ 110-89-4 ]
  • [ 1060816-22-9 ]
  • ethyl 2-(piperidin-1-yl)-1,3-oxazole-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% at 150℃; for 0.5h;Microwave irradiation; A 5-ml, microwave tube was charged with ethyl2-bromo-i,3-oxazole-5-carboxylate (500 mg, 2.27 mmol), piperidine (219 mg, 2.57 mmol) and (trifluoromethyl)benzene (2 mE). The final reaction mixture was irradiated with microwave radiation for 30 mm at 150 C. The resulting solution was cooled to 23 C. and concentrated under vacuum. The residue was purified by column chromatography eluting with ethyl acetate/petroleum ether (1:1 v/v) to afford ethyl 2-(piperidin- i-yr-i ,3-oxazole-5-carboxylate as a white solid (400 mg, 78%). ECMS: (ESI) mlz 225 [M+H].
  • 5
  • [ 1060816-22-9 ]
  • [ 411235-57-9 ]
  • ethyl 2-cyclopropyl-1,3-oxazole-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In water; toluene; at 120℃; for 16h;Inert atmosphere; A 100-mE round-bottom flask purged and maintained with an inert atmosphere of nitrogen was charged with ethyl 2-bromo-1 ,3-oxazole-5-carboxylate (600 mg, 2.73 mmol), cyclopropylboronic acid (377 mg, 4.39 mmol), toluene (30 mE, 282 mmol), potassium phosphate (1.59 g, 7.49 mmol) in water (4 mE) and 1, 1?-(diphenyl phosphine) ferrocene methylene chloride palladium dichioride (12mg, 0.06 mmol). The solution was stirred for 16 hat 120 C. in an oil bath. The reaction quenched with water (10 mE) and the combined organic layers were dried over anhydrous sodium sulfate, filtrated and concentrated under vacuum. The residue was purified by column chromatography eluting with ethyl acetate/petroleum ether (1:20 to 1:5 v/v) to give ethyl 2-cy- clopropyl-1,3-oxazole-5-carboxylate (70 mg, 61%). LCMS (ES) mlz 182 [M+H].
  • 6
  • [ 1060816-22-9 ]
  • [ 137504-86-0 ]
  • ethyl 2-(4-chloro-3-fluorophenyl)oxazole-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% With tris-(dibenzylideneacetone)dipalladium(0); 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane; potassium carbonate; In tetrahydrofuran; water; at 65℃; for 12h; A mixture of <strong>[1060816-22-9]ethyl 2-bromooxazole-5-carboxylate</strong> (ArkPharm Inc., 1 g, 4.55 mmol), (4- chloro-3-fluorophenyl)boronic acid (Combi-Blocks, 0.99 g, 5.68 mmol), (1S,3R,5R,7S)-1,3,5,7- tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphaadamantane (Strem, 0.133 g, 0.455 mmol), bis(dibenzylideneacetone)palladium (0) (Strem, 0.13 g, 0.23 mmol) and potassium carbonate (1.57 g, 11.4 mmol) in a pressure tube was degassed three times with a nitrogen back flush each time. Tetrahydrofuran (15 mL) and water (3.0 mL) were added, and the mixture was again degassed three times with a nitrogen back flush each time. The reaction mixture was warmed to 65 C and was allowed to stir for 12 hours. The mixture was allowed to cool to ambient temperature, anhydrous Na2SO4 was added, and the mixture was filtered through diatomaceous earth. The filtrate was concentrated under reduced pressure, and the residue was purified via column chromatography (SiO2, 1-50% ethyl acetate/heptanes) to give the title compound (0.41 g, 1.52 mmol, 34% yield). MS (ESI+) m/z 270 (M+H)+.
34% With tris-(dibenzylideneacetone)dipalladium(0); (1S,3R,5R,7S)-1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphaadamantane; potassium carbonate; In tetrahydrofuran; water; at 65℃; for 12h;Sealed tube; Inert atmosphere; A mixture of <strong>[1060816-22-9]ethyl 2-bromooxazole-5-carboxylate</strong> (ArkPharm Inc., 1 g, 4.55 mmol), (4- chloro-3-fluorophenyl)boronic acid (Combi-Blocks, 0.99 g, 5.68 mmol), (15,3R,5R,75)-1,3,5,7- tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphaadamantane (Strem, 0.133 g, 0.455 mmol), bis(dibenzylideneacetone)palladium (0) (Strem, 0.13 g, 0.23 mmol) and potassium carbonate (1.57 g, 11.4 mmol) in a pressure tube was degassed three times with a nitrogen back flush each time. Tetrahydrofuran (15 mL) and water (3.0 mL) were added, and the mixture was again degassed three times with a nitrogen back flush each time. The reaction mixture was warmed to 65 C and was allowed to stir for 12 hours. The mixture was allowed to cool to ambient temperature, anhydrous Na2SC>4 was added, and the mixture was filtered through diatomaceous earth. The filtrate was concentrated under reduced pressure, and the residue was purified via column chromatography (Si(, 1-50% ethyl acetate/heptanes) to give the title compound (0.41 g, 1.52 mmol, 34% yield). MS (ESI+) m/z 270 (M+H)+.
  • 7
  • [ 1060816-22-9 ]
  • [ 1218790-39-6 ]
  • ethyl 2-(6-(trifluoromethyl)pyridin-3-yl)oxazole-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With tris-(dibenzylideneacetone)dipalladium(0); 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane; potassium carbonate; In tetrahydrofuran; water; at 65℃; for 12h; A mixture of ethyl-2-bromooxazole-5-carboxylate (0.50 g, 2.27 mmol), 5-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)pyridine (Combi-Blocks, 0.78 g, 2.84 mmol), (1S,3R,5R,7S)-1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphaadamantane (Strem, 0.066 g, 0.23 mmol), bis(dibenzylideneacetone)palladium (0) (0.065 g, 0.114 mmol) and potassium carbonate (0.79 g, 5.68 mmol) in a pressure tube was degassed three times with a nitrogen back flush each time. Tetrahydrofuran (7.5 mL) and water (1.5 mL) were added, and the mixture was again degassed three times with a nitrogen back flush each time. The reaction mixture was warmed to 65 C and was allowed to stir for 12 hours. The mixture was allowed to cool to ambient temperature, then anhydrous Na2SO4 was added, and the mixture was filtered through diatomaceous earth. The filtrate was concentrated under reduced pressure, and the residue was purified via column chromatography (SiO2, 1-40% ethyl acetate/heptanes) to give the title compound (0.43 g, 1.50 mmol, 66% yield). MS (ESI+) m/z 287 (M+H)+.
66% With tris-(dibenzylideneacetone)dipalladium(0); (1S,3R,5R,7S)-1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphaadamantane; potassium carbonate; In tetrahydrofuran; water; at 65℃; for 12h;Inert atmosphere; Sealed tube; A mixture of ethyl-2-bromooxazole-5-carboxylate (0.50 g, 2.27 mmol), 5-(4,4,5,5- tetramethyl-l ,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)pyridine (Combi-B locks, 0.78 g, 2.84 mmol), (15,3R,5R,75)-l ,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphaadamantane (Strem, 0.066 g, 0.23 mmol), bis(dibenzylideneacetone)palladium (0) (0.065 g, 0.114 mmol) and potassium carbonate (0.79 g, 5.68 mmol) in a pressure tube was degassed three times with a nitrogen back flush each time. Tetrahydrofuran (7.5 mL) and water (1.5 mL) were added, and the mixture was again degassed three times with a nitrogen back flush each time. The reaction mixture was warmed to 65 C and was allowed to stir for 12 hours. The mixture was allowed to cool to ambient temperature, then anhydrous Na2SC>4 was added, and the mixture was filtered through diatomaceous earth. The filtrate was concentrated under reduced pressure, and the residue was purified via column chromatography (Si(, 1-40% ethyl acetate/heptanes) to give the title compound (0.43 g, 1.50 mmol, 66% yield). MS (ESI+) m/z 287 (M+H)+.
  • 8
  • [ 1060816-22-9 ]
  • [ 1052686-67-5 ]
  • ethyl 2-(2-methylpyrimidin-5-yl)oxazole-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With tris-(dibenzylideneacetone)dipalladium(0); 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane; potassium carbonate; In tetrahydrofuran; water; at 65℃; for 16h; A mixture of <strong>[1060816-22-9]ethyl 2-bromooxazole-5-carboxylate</strong> (0.50 g, 2.3 mmol), 2- methylpyrimidine-5-boronic acid pinacol ester (0.625 g, 2.84 mmol) , (1S,3R,5R,7S)-1,3,5,7- tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphaadamantane (0.066 g, 0.23 mmol), bis(dibenzylideneacetone)palladium (0) (0.065 g, 0.11 mmol) and potassium carbonate (0.79 g, 5.7 mmol) in a pressure tube was degassed three times with a nitrogen back flush each time. Tetrahydrofuran (7.5 mL) and water (1.5 mL) were added, and the mixture was again degassed three times with a nitrogen back flush each time. The reaction mixture was warmed to 65 C and stirred for 16 hours. The mixture was allowed to cool to ambient temperature, then anhydrous Na2SO4 was added, and the mixture was filtered through diatomaceous earth. The filtrate was then concentrated under reduced pressure. The residue was purified via column chromatography (SiO2, 1-40% ethyl acetate/heptanes) to give the title compound (0.295 g, 1.27 mmol, 56% yield). MS (ESI+) m/z 234 (M+H)+.
56% With tris-(dibenzylideneacetone)dipalladium(0); (1S,3R,5R,7S)-1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphaadamantane; potassium carbonate; In tetrahydrofuran; water; at 65℃; for 16h;Inert atmosphere; Sealed tube; A mixture of <strong>[1060816-22-9]ethyl 2-bromooxazole-5-carboxylate</strong> (0.50 g, 2.3 mmol), 2- methylpyrimidine-5-boronic acid pinacol ester (0.625 g, 2.84 mmol) , (15,3R,5R,75)-1 , 3,5,7- tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphaadamantane (0.066 g, 0.23 mmol), bis(dibenzylideneacetone)palladium (0) (0.065 g, 0.11 mmol) and potassium carbonate (0.79 g, 5.7 mmol) in a pressure tube was degassed three times with a nitrogen back flush each time. Tetrahydrofuran (7.5 mL) and water (1.5 mL) were added, and the mixture was again degassed three times with a nitrogen back flush each time. The reaction mixture was warmed to 65 C and stirred for 16 hours. The mixture was allowed to cool to ambient temperature, then anhydrous Na2SC>4 was added, and the mixture was filtered through diatomaceous earth. The filtrate was then concentrated under reduced pressure. The residue was purified via column chromatography (Si(, 1-40% ethyl acetate/heptanes) to give the title compound (0.295 g, 1.27 mmol, 56% yield). MS (ESI+) m/z 234 (M+H)+.
  • 9
  • [ 1227068-84-9 ]
  • [ 1060816-22-9 ]
  • ethyl 2-(4,4-difluorocyclohex-1-en-1-yl)oxazole-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With tris-(dibenzylideneacetone)dipalladium(0); 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane; potassium carbonate; In tetrahydrofuran; water; at 65℃; for 12h;Sealed tube; A mixture of ethyl 2-bromooxazole-5-carboxylate (Ark Pharm, 0.26 g, 1.182 mmol), 2- (4,4-difluorocyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (Emolecules, 0.288 g, 1.182 mmol), (1S,3R,5R,7S)-1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8- phosphaadamantane (Aldrich, 0.035 g, 0.118 mmol), bis(dibenzylideneacetone)palladium (Strem, 0.034 g, 0.059 mmol) and potassium carbonate (0.408 g, 2.95 mmol) in a pressure tube were degassed three times with a nitrogen back flush each time. Then tetrahydrofuran (5.0 mL) and water (1.0 mL) were added, and the mixture was again degassed three times with a nitrogen back flush each time. The reaction mixture was sealed and stirred at 65 C for 12 hours. The mixture was allowed to cool to ambient temperature, then anhydrous sodium sulfate was added, and the mixture was filtered through a pack of diatomaceous earth. The filtrate was concentrated under reduced pressure. The residue was purified via flash chromatography (SiO2, 1-40% ethyl acetate in heptane) to give the title compound (0.255 g, 0.991 mmol, 84% yield). MS (ESI+) m/z 258 (M+H)+.
84% With tris-(dibenzylideneacetone)dipalladium(0); (1S,3R,5R,7S)-1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphaadamantane; potassium carbonate; In tetrahydrofuran; water; at 65℃; for 12h;Inert atmosphere; Sealed tube; A mixture of ethyl 2-bromooxazole-5-carboxylate (Ark Pharm, 0.26 g, 1.182 mmol), 2- (4,4-difluorocyclohex-l-en-l-yl)-4,4,5,5-tetramethyl-l ,3,2-dioxaborolane (Emolecules, 0.288 g, 1.182 mmol), (15,3R,5R,75)-l ,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphaadamantane (Aldrich, 0.035 g, 0.118 mmol), bis(dibenzylideneacetone)palladium (Strem, 0.034 g, 0.059 mmol) and potassium carbonate (0.408 g, 2.95 mmol) in a pressure tube were degassed three times with a nitrogen back flush each time. Then tetrahydrofuran (5.0 mL) and water (1.0 mL) were added, and the mixture was again degassed three times with a nitrogen back flush each time. The reaction mixture was sealed and stirred at 65 C for 12 hours. The mixture was allowed to cool to ambient temperature, then anhydrous sodium sulfate was added, and the mixture was filtered through a pack of diatomaceous earth. The filtrate was concentrated under reduced pressure. The residue was purified via flash chromatography (Si(, 1-40% ethyl acetate in heptane) to give the title compound (0.255 g, 0.991 mmol, 84% yield). MS (ESI+) m/z 258 (M+H)+.
  • 10
  • [ 1060816-22-9 ]
  • [ 287944-16-5 ]
  • ethyl 2-(3,6-dihydro-2H-pyran-4-yl)oxazole-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,2-dimethoxyethane; water; at 115℃; for 0.583333h;Microwave irradiation; Dimethoxyethane (10 mL) and water (1 mL) were added to a mixture of ethyl 2- bromooxazole-5-carboxylate (Ark Pharm, 334 mg, 1.52 mmol), 3,6-dihydro-2H-pyran-4- boronic acid pinacol ester (Combi-Blocks, 319 mg, 1.52 mmol) , [1,1'- bis(diphenylphosphino)ferrocene]dichloropalladium(II) (89 mg, 0.12 mmol) and potassium carbonate (525 mg, 3.80 mmol) in a microwave tube. The tube was sealed and degassed three times with a nitrogen back flush each time. The tube was heated in a Biotage Initiator+ microwave reactor and irradiated at 115 C for 35 minutes. The seal was opened, and the reaction mixture was combined with silica gel (15 g) and concentrated under reduced pressure to a free flowing powder. The powder was directly purified via flash chromatography (SiO2, 15-100% ethyl acetate in heptane) to give the title compound (0.24 g, 1.08 mmol, 71% yield). MS (ESI+) m/z 224 (M+H)+.
71% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,2-dimethoxyethane; water; at 115℃; for 0.583333h;Inert atmosphere; Sealed tube; Microwave irradiation; Dimethoxyethane (10 mL) and water (1 mL) were added to a mixture of ethyl 2- bromooxazole-5-carboxylate (Ark Pharm, 334 mg, 1.52 mmol), 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester (Combi-B locks, 319 mg, 1.52 mmol) , [Iota,Gamma- bis(diphenylphosphino)ferrocene]dichloropalladium(II) (89 mg, 0.12 mmol) and potassium carbonate (525 mg, 3.80 mmol) in a microwave tube. The tube was sealed and degassed three times with a nitrogen back flush each time. The tube was heated in a Biotage Initiator+ microwave reactor and irradiated at 115 C for 35 minutes. The seal was opened, and the reaction mixture was combined with silica gel (15 g) and concentrated under reduced pressure to a free flowing powder. The powder was directly purified via flash chromatography (Si(, 15- 100% ethyl acetate in heptane) to give the title compound (0.24 g, 1.08 mmol, 71 % yield). MS (ESI+) m/z 224 (M+H)+.
  • 11
  • [ 118994-89-1 ]
  • [ 1060816-22-9 ]
YieldReaction ConditionsOperation in experiment
68% Under a argon atmosphere, tetrahydrofuran (500 mL) was added to the reaction flask andCompound 1 is <strong>[118994-89-1]oxazole-5-carboxylic acid ethyl ester</strong> (32 g 0.23 mol 1 eq). The temperature was lowered to -70 to -80 C, and then LiHMDS (250 ml, 0.25 mol, 1.1 eq.) was slowly added dropwise.After the dropwise addition, the temperature was kept at -70 to -80 C, and the reaction was stirred for 10 minutes.CBr4 (106 g, 0.32 mol, 1.4 eq.) was added in portions, and after the addition, the temperature was kept at -70 to -80 C, and the reaction was stirred for 2 hours.After extraction with saturated ammonium chloride, it was slowly warmed to room temperature.Extract with ethyl acetate (250 mL * 2), wash with water (250 mL * 2), and wash with saturated brine (250 mL * 1).Concentrated and mixed with the column to obtain 34.4 g of product, the yield was 68%.
  • 12
  • [ 1060816-22-9 ]
  • [ 329214-79-1 ]
  • ethyl 2-(pyridin-3-yl)oxazole-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
5% With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane; In 1,2-dimethoxyethane; water; at 78℃; for 0.333333h;Sealed tube; Inert atmosphere; 1 ,2-Dimethoxyethane (9 mL) and water (1 mL) were added to a sealed tube (20 mL) containing a mixture of 3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine (373 mg, 1.82 mmol, Aurum Pharmatech), potassium carbonate (628 mg, 4.55 mmol), l,3,5,7-tetramethyl-6- phenyl-2,4,8-trioxa-6-phosphaadamantane (53.1 mg, 0.18 mmol, Aldrich), tris(dibenzylideneacetone)dipalladium(0) (41.6 mg, 0.045 mmol) and ethyl 2-bromooxazole-5- carboxylate (400mg, 1.82 mmol, Ark Pharm). The tube was sealed and degassed three times with a nitrogen backflush each time. It was then heated at 78 C for 20 minutes. The tube was cooled, and the reaction mixture was combined with diatomaceous earth (15 g) and concentrated under reduced pressure to a free flowing powder. The powder was directly purified via reverse phase flash chromatography [custom packed YMC TriArt C18 Hybrid 20 mupiiota column, 25 x 100 mm, flow rate 35 mL/minute, 5-100% gradient of acetonitrile in buffer (0.025 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)] to give the title compound (21 mg, 0.096 mmol, 5% yield). JH NMR (501 MHz, DMSO-<) delta ppm 9.21 (dd, J = 2.3, 0.9 Hz, 1H), 8.79 (dd, J = 4.8, 1.7 Hz, 1H), 8.40 (ddd, J = 8.0, 2.3, 1.7 Hz, 1H), 8.18 (s, 1H), 7.63 (ddd, J = 8.0, 4.8, 0.9 Hz, 1H), 4.38 (q, J = 7.1 Hz, 2H), 1.34 (t, J = 7.1 Hz, 3H); MS (APCI+) m/z 219 (M+H)+.
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2-Bromooxazole-5-carboxylic acid hydrate

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Chemical Structure| 1373253-25-8

[ 1373253-25-8 ]

2-Bromooxazole-5-carboxylic acid

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Chemical Structure| 78451-13-5

[ 78451-13-5 ]

Ethyl 2-bromo-4-methyloxazole-5-carboxylate

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Chemical Structure| 1823898-69-6

[ 1823898-69-6 ]

Methyl 2-bromo-4-methyloxazole-5-carboxylate

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Esters

Chemical Structure| 1092351-96-6

[ 1092351-96-6 ]

Methyl 2-bromooxazole-5-carboxylate

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Chemical Structure| 78451-13-5

[ 78451-13-5 ]

Ethyl 2-bromo-4-methyloxazole-5-carboxylate

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Chemical Structure| 1823898-69-6

[ 1823898-69-6 ]

Methyl 2-bromo-4-methyloxazole-5-carboxylate

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Chemical Structure| 118994-89-1

[ 118994-89-1 ]

Ethyl oxazole-5-carboxylate

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Chemical Structure| 121432-12-0

[ 121432-12-0 ]

Methyl 5-oxazolecarboxylate

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Related Parent Nucleus of
[ 1060816-22-9 ]

Oxazoles

Chemical Structure| 1092351-96-6

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Methyl 2-bromooxazole-5-carboxylate

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Chemical Structure| 1619264-49-1

[ 1619264-49-1 ]

2-Bromooxazole-5-carboxylic acid hydrate

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Chemical Structure| 1373253-25-8

[ 1373253-25-8 ]

2-Bromooxazole-5-carboxylic acid

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Chemical Structure| 78451-13-5

[ 78451-13-5 ]

Ethyl 2-bromo-4-methyloxazole-5-carboxylate

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Chemical Structure| 1823898-69-6

[ 1823898-69-6 ]

Methyl 2-bromo-4-methyloxazole-5-carboxylate

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