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[ CAS No. 1123169-23-2 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 1123169-23-2
Chemical Structure| 1123169-23-2
Chemical Structure| 1123169-23-2
Structure of 1123169-23-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1123169-23-2 ]

CAS No. :1123169-23-2 MDL No. :MFCD11858439
Formula : C9H6BrNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :OAHWOZBMLUMQBM-UHFFFAOYSA-N
M.W : 256.05 Pubchem ID :71463788
Synonyms :

Calculated chemistry of [ 1123169-23-2 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.11
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 52.99
TPSA : 52.33 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
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) : 2.58
Log Po/w (WLOGP) : 2.38
Log Po/w (MLOGP) : 1.76
Log Po/w (SILICOS-IT) : 2.38
Consensus Log Po/w : 2.32

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.4
Solubility : 0.103 mg/ml ; 0.000401 mol/l
Class : Soluble
Log S (Ali) : -3.33
Solubility : 0.12 mg/ml ; 0.000471 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.85
Solubility : 0.0364 mg/ml ; 0.000142 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.53

Safety of [ 1123169-23-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1123169-23-2 ]

* 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 [ 1123169-23-2 ]

[ 1123169-23-2 ] Synthesis Path-Downstream   1~33

  • 1
  • [ 1123169-23-2 ]
  • [ 1971108-53-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: lithium borohydride / tetrahydrofuran; methanol / 0.5 h / 0 °C 2.1: triphenylphosphine / tetrahydrofuran; methanol / 0.08 h / 0 °C / Microwave irradiation 2.2: 0 - 20 °C 3.1: caesium carbonate; XPhos; tris(dibenzylideneacetone)dipalladium(0) chloroform complex / 1,4-dioxane / 0.5 h / 140 °C / Sealed tube; Inert atmosphere; Microwave irradiation 4.1: trifluoroacetic acid / 1,4-dioxane / 0.5 h / 130 °C / Microwave irradiation
  • 2
  • [ 1123169-23-2 ]
  • [ 1971108-60-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: lithium borohydride / tetrahydrofuran; methanol / 0.5 h / 0 °C 2.1: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C 3.1: acetic acid / 1,2-dichloro-ethane / 0.75 h / 45 °C 3.2: 0.17 h 4.1: sodium t-butanolate; methanesulfonato(2-di-t-butylphosphino-2’,4’,6’-tri-i-propyl-1,1'-biphenyl)(2’-amino-1,1'-biphenyl-2-yl)palladium(II); C37H56ClNPPd / <i>tert</i>-butyl alcohol / 12 h / 75 °C / Inert atmosphere 5.1: trifluoroacetic acid / 0.25 h / 150 °C
  • 3
  • [ 1123169-23-2 ]
  • [ 1971108-84-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: lithium borohydride / tetrahydrofuran; methanol / 0.5 h / 0 °C 2: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C 3: tetrahydrofuran / 2 h / -78 °C 4: diethylamino-sulfur trifluoride / 1,2-dichloro-ethane / 20 °C 5: caesium carbonate; XPhos; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 1 h / 140 °C / Inert atmosphere; Microwave irradiation 6: hydrogenchloride / 1,4-dioxane / 3 h / 0 - 20 °C 7: caesium carbonate; XPhos; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 100 °C / Inert atmosphere; Microwave irradiation 8: hydrogenchloride / 1,4-dioxane / 20 - 45 °C
  • 4
  • [ 1123169-23-2 ]
  • [ 1971109-17-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: lithium borohydride / tetrahydrofuran; methanol / 0.5 h / 0 °C 2: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C 3: sodium hydroxide / toluene / 0.25 h / 20 °C 4: tetrabutylammonium triphenyldifluorosilicate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 5: acetic acid; N-ethyl-N,N-diisopropylamine / 1 h / 90 °C 6: sodium t-butanolate; methanesulfonato(2-di-t-butylphosphino-2’,4’,6’-tri-i-propyl-1,1'-biphenyl)(2’-amino-1,1'-biphenyl-2-yl)palladium(II) / <i>tert</i>-butyl alcohol / 3 h / 60 °C / Inert atmosphere 7: trifluoroacetic acid / 0.5 h / 130 °C / Microwave irradiation
  • 5
  • [ 1123169-23-2 ]
  • [ 1824292-23-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium borohydride / tetrahydrofuran; methanol / 0.5 h / 0 °C 2: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C
  • 6
  • [ 1123169-23-2 ]
  • [ 1971109-27-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: lithium borohydride / tetrahydrofuran; methanol / 0.5 h / 0 °C 2: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C 3: methanol / 20 °C
  • 7
  • [ 1123169-23-2 ]
  • [ 1785533-28-9 ]
YieldReaction ConditionsOperation in experiment
With lithium borohydride In tetrahydrofuran; methanol at 0℃; for 0.5h; 45 48 2Π'ΡΑ, toSuene, 150* C, MW(45) . A solution of the starting material in THF (58.5 mL, 0.2 M) was cooled to 0 °C. To the reaction was added a solution ofLiBHt in THF and MeOH. After 30 min at 0 *€, the reaction was quenched with .15% NaOH aqueous solution. The reaction was allowed to warm to room temp, and the filtrate was coilecicd and eoiiceiitrated. The residue was added to water and EtOAc. The aqueous layer was extracted with EtOAc 3X. The organic extraction was washed with brine 1 X and dried over gSO*. The solution, was concentrated to afford the product which was used for future reactions without further purification.Scheme XX(70). To a sohition of methyl 6- roniobeiizoidjisoxazole-3-carboxy.ate~( l .123169-23-2) (Sg,19.53raraol) in THP (25mL) at if C was added a solution of lithium borohydride-( 16949-15-8) (2M, 19.53.oiL, 39.05mmol) in THF and methanol. After 30 min at 0° C, water (30mL) was added. After 20 min at ft, the reaction was diluted with EtOAc, The organic layer was extracted, and washed with water, briiie, and dried over MgSO* to yield (6-bronio~l,2-beiizoxa2:o~3-y].)methano]. (4.3g, .l8.86mmo.1, 97%yieid). ES-MS {MHf : 230.3, RT - 0.807 rain, >98% at 254 m.
  • 8
  • [ 1123169-23-2 ]
  • [ 1971109-34-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: lithium borohydride / tetrahydrofuran; methanol / 0.5 h / 0 °C 2.1: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C 3.1: acetic acid / 1,2-dichloro-ethane / 0.75 h / 45 °C 3.2: 0.17 h
  • 9
  • [ 1123169-23-2 ]
  • [ 1971109-39-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: lithium borohydride / tetrahydrofuran; methanol / 0.5 h / 0 °C 2: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C 3: ammonium chloride / tetrahydrofuran / 2 h / -78 °C 4: Dess-Martin periodane / dichloromethane / 1 h / 20 °C
  • 10
  • [ 1123169-23-2 ]
  • [ 1971109-38-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: lithium borohydride / tetrahydrofuran; methanol / 0.5 h / 0 °C 2: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C 3: ammonium chloride / tetrahydrofuran / 2 h / -78 °C
  • 11
  • [ 1123169-23-2 ]
  • [ 1971109-42-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: lithium borohydride / tetrahydrofuran; methanol / 0.5 h / 0 °C 2: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C 3: tetrahydrofuran / 2 h / -78 °C
  • 12
  • [ 1123169-23-2 ]
  • [ 1971109-43-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: lithium borohydride / tetrahydrofuran; methanol / 0.5 h / 0 °C 2: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C 3: tetrahydrofuran / 2 h / -78 °C 4: diethylamino-sulfur trifluoride / 1,2-dichloro-ethane / 20 °C
  • 13
  • [ 1123169-23-2 ]
  • [ 1971109-45-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: lithium borohydride / tetrahydrofuran; methanol / 0.5 h / 0 °C 2: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C 3: tetrahydrofuran / 2 h / -78 °C 4: diethylamino-sulfur trifluoride / 1,2-dichloro-ethane / 20 °C 5: caesium carbonate; XPhos; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 1 h / 140 °C / Inert atmosphere; Microwave irradiation 6: hydrogenchloride / 1,4-dioxane / 3 h / 0 - 20 °C
  • 14
  • [ 1123169-23-2 ]
  • [ 1971109-44-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: lithium borohydride / tetrahydrofuran; methanol / 0.5 h / 0 °C 2: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C 3: tetrahydrofuran / 2 h / -78 °C 4: diethylamino-sulfur trifluoride / 1,2-dichloro-ethane / 20 °C 5: caesium carbonate; XPhos; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 1 h / 140 °C / Inert atmosphere; Microwave irradiation
  • 15
  • [ 1123169-23-2 ]
  • [ 1971109-46-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: lithium borohydride / tetrahydrofuran; methanol / 0.5 h / 0 °C 2: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C 3: tetrahydrofuran / 2 h / -78 °C 4: diethylamino-sulfur trifluoride / 1,2-dichloro-ethane / 20 °C 5: caesium carbonate; XPhos; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 1 h / 140 °C / Inert atmosphere; Microwave irradiation 6: hydrogenchloride / 1,4-dioxane / 3 h / 0 - 20 °C 7: caesium carbonate; XPhos; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 100 °C / Inert atmosphere; Microwave irradiation
  • 16
  • [ 1123169-23-2 ]
  • [ 1971109-51-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: lithium borohydride / tetrahydrofuran; methanol / 0.5 h / 0 °C 2.1: triphenylphosphine / tetrahydrofuran; methanol / 0.08 h / 0 °C / Microwave irradiation 2.2: 0 - 20 °C
  • 17
  • [ 1123169-23-2 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: lithium borohydride / tetrahydrofuran; methanol / 0.5 h / 0 °C 2.1: triphenylphosphine / tetrahydrofuran; methanol / 0.08 h / 0 °C / Microwave irradiation 2.2: 0 - 20 °C 3.1: caesium carbonate; XPhos; tris(dibenzylideneacetone)dipalladium(0) chloroform complex / 1,4-dioxane / 0.5 h / 140 °C / Sealed tube; Inert atmosphere; Microwave irradiation
  • 18
  • [ 1123169-23-2 ]
  • [ 1971109-52-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: lithium borohydride / tetrahydrofuran; methanol / 0.5 h / 0 °C 2: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C 3: sodium hydroxide / toluene / 0.25 h / 20 °C
  • 19
  • [ 1123169-23-2 ]
  • [ 1971109-53-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: lithium borohydride / tetrahydrofuran; methanol / 0.5 h / 0 °C 2: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C 3: sodium hydroxide / toluene / 0.25 h / 20 °C 4: tetrabutylammonium triphenyldifluorosilicate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
  • 20
  • [ 1123169-23-2 ]
  • [ 1971109-56-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: lithium borohydride / tetrahydrofuran; methanol / 0.5 h / 0 °C 2: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C 3: sodium hydroxide / toluene / 0.25 h / 20 °C 4: tetrabutylammonium triphenyldifluorosilicate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 5: acetic acid; N-ethyl-N,N-diisopropylamine / 1 h / 90 °C
  • 21
  • [ 1123169-23-2 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: lithium borohydride / tetrahydrofuran; methanol / 0.5 h / 0 °C 2.1: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C 3.1: acetic acid / 1,2-dichloro-ethane / 0.75 h / 45 °C 3.2: 0.17 h 4.1: sodium t-butanolate; methanesulfonato(2-di-t-butylphosphino-2’,4’,6’-tri-i-propyl-1,1'-biphenyl)(2’-amino-1,1'-biphenyl-2-yl)palladium(II); C37H56ClNPPd / <i>tert</i>-butyl alcohol / 12 h / 75 °C / Inert atmosphere
  • 22
  • [ 1123169-23-2 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: lithium borohydride / tetrahydrofuran; methanol / 0.5 h / 0 °C 2: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C 3: sodium hydroxide / toluene / 0.25 h / 20 °C 4: tetrabutylammonium triphenyldifluorosilicate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 5: acetic acid; N-ethyl-N,N-diisopropylamine / 1 h / 90 °C 6: sodium t-butanolate; methanesulfonato(2-di-t-butylphosphino-2’,4’,6’-tri-i-propyl-1,1'-biphenyl)(2’-amino-1,1'-biphenyl-2-yl)palladium(II) / <i>tert</i>-butyl alcohol / 3 h / 60 °C / Inert atmosphere
  • 23
  • [ 1123169-23-2 ]
  • [ 1971107-69-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: lithium borohydride / tetrahydrofuran; methanol / 0.5 h / 0 °C 2.1: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C 3.1: methanol / 20 °C 4.1: potassium carbonate; trifluoroacetic acid / 1,4-dioxane / 110 °C / Microwave irradiation 5.1: caesium carbonate; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 0.05 h / 20 °C / Inert atmosphere 5.2: 0.5 h / 140 °C / Microwave irradiation 6.1: trifluoroacetic acid / 0.5 h / 130 °C / Microwave irradiation
  • 24
  • [ 1123169-23-2 ]
  • [ 2040302-94-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: lithium borohydride / tetrahydrofuran; methanol / 0.5 h / 0 °C 2: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C 3: methanol / 20 °C 4: potassium carbonate; trifluoroacetic acid / 1,4-dioxane / 110 °C / Microwave irradiation
  • 25
  • [ 1123169-23-2 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: lithium borohydride / tetrahydrofuran; methanol / 0.5 h / 0 °C 2.1: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C 3.1: methanol / 20 °C 4.1: potassium carbonate; trifluoroacetic acid / 1,4-dioxane / 110 °C / Microwave irradiation 5.1: caesium carbonate; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 0.05 h / 20 °C / Inert atmosphere 5.2: 0.5 h / 140 °C / Microwave irradiation
  • 26
  • [ 1123169-17-4 ]
  • [ 18107-18-1 ]
  • [ 1123169-23-2 ]
YieldReaction ConditionsOperation in experiment
43% In tetrahydrofuran; methanol at 0 - 20℃; for 0.5h; 38.1 Step 1. Methyl 6-bromo-l,2-benzoxazole-3-carboxylate (29b) To a 100-mL round-bottom flask was added a solution of 6-bromo-l ,2-benzoxazole-3- carboxylic acid 29a (400 mg, 1.65 mmol, 1.0 equiv.) in tetrahydrofuran/MeOH (10/10 mL),followed by the drop wise addition of TMSCHN2 (1.65 mL, 2.0 equiv.) at 0 °C. The resulting mixture was stirred for 30 min at RT and then concentrated in vacuo. The residue was purified via silica gel column chromatography eluting with ethyl acetate/petroleum ether (1 :5) to give of methyl 6-bromo-l,2-benzoxazole-3-carboxylate 29b (180 mg, 43%) as an off-white solid.
  • 27
  • [ 1123169-23-2 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate / toluene / 110 °C 2: potassium <i>tert</i>-butylate / tetrahydrofuran / 3 h / 20 °C
  • 28
  • [ 1123169-23-2 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate / toluene / 110 °C 2: potassium <i>tert</i>-butylate / tetrahydrofuran / 3 h / 20 °C 3: N,N-dimethyl-formamide / 0.17 h / 20 °C / Sealed tube
  • 29
  • [ 1123169-23-2 ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
27% With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 110℃; 38.2 Step 2. Methyl 6-[(lR,3R,5S)-3-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-l,2-oxazol-4- yI]e,arbo8iyloxy]-8-azab8cyeIo[3,2J]octa8i-8-yIj-i,2-be8izoxazoIe-"3-earboxylate (29c) To a 50 mL round-bottom flask purged with nitrogen was added methyl 6-bromo-l,2- benzoxazole-3-carboxylate 29b (20 mg, 0.08 mmol, 1.2 equiv.) in toluene (2 mL), (lR,3R,5S)-8- azabicyclo[3.2.1]octan-3-yl 5-cyclopropyl-3-(2,6-dichlorophenyl)-l ,2-oxazole-4-carboxylate Ij (26 mg, 0.06 mmol, 1.0 equiv.), BINAP (8 mg, 0.01 mmol, 0.2 equiv.), CsiCCb (52 mg, 0. 16 mmol, 2,5 equiv.), and Pd2(dba)3 (13 mg, 0,01 mmol, 0,2 equiv,). The resulting solution was stirred at 1 10 °C overnight. The resulting mixture was concentrated in vacuo. The residue was purified via silica gel column chromatography eluting with ethyl acetate/petroleum ether (1 :5) to give methyl 6-[(lR,3R,5S)-3-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-l,2-oxazol-4- yl]carbonyloxy]-8-azabicyclo[3.2. l]octan-8-yl]-l,2-benzoxazole-3-carboxylate 29c (10 mg, 27%) as a yellow solid.
  • 30
  • [ 1013-88-3 ]
  • [ 1123169-23-2 ]
  • [ 2408309-30-6 ]
YieldReaction ConditionsOperation in experiment
85% With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 100℃; for 12h; 50-a (Example 50-a) Methyl 6-[(dipheny1methy1idene)amino-1,2-benzoxazole-3-carboxylate To a solution of methyl 6-bromo-1,2-benzoxazole-3- carboxylate (0.50 g, 2.0 mmol) in toluene (20 mL) were added benzophenone imine (0.50 ml, 2.9 mmol), cesium carbonate (1.1 g, 2.9 mmcl), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene, (0.24 g, 0.39 mmol), and palladium(II) acetate (53 mg, 0.20 mmcl) . The mixture was stirred at 100°C for 12 h. The reaction solution was concentrated. The obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane =0:100 to 70:30) to give the title compound (0.59 g,1.7 mmcl, 85%) as a solid.‘H NNR (500 MHz, CDC1,) ö (ppm) 4.04 (s, 3H), 6.85 (dd,J = 8.8, 1.5 Hz, 1H), 6.92 (d, J = 1.0 Hz, 1H), 7.08-7.17(m, 2H), 7.22-7.32 (m, 3H), 7.41-7.55 (m, 3H), 7.77-7.87(m, 3H)LCMS (ES) : m/z 357 [M+H.
  • 31
  • [ 1123169-23-2 ]
  • [ 2408309-31-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: caesium carbonate; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / toluene / 12 h / 100 °C 2: hydrogenchloride / dichloromethane; 1,4-dioxane / 12 h / 20 °C
  • 32
  • [ 21987-29-1 ]
  • [ 1123169-23-2 ]
  • [ 2758682-22-1 ]
YieldReaction ConditionsOperation in experiment
310 mg With methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II); caesium carbonate In 1,4-dioxane at 20℃; Inert atmosphere; Step 1: methyl 6-(4,4-difluoropiperidin-1-yl)-1,2-benzoxazole-3-carboxylate Methyl 6-bromo-1,2-benzoxazole-3-carboxylate (1.0 g, 3.9 mmol, 1.0 equiv.) and 4,4-difluoropiperidine (473.1 mg, 3.9 mmol, 1.0 equiv.) were dissolved in 1,4-dioxane (8 mL), then Xphos Pd G3 (330.6 mg, 0.4 mmol, 0.1 equiv.) and Cs2CO3(3.8 g, 11.7 mmol, 3.0 equiv.) were added under an atmosphere of nitrogen. The reaction mixture was stirred overnight at ambient temperature and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel, eluting with ethyl acetate/petroleum ether (1:2) to give methyl 6-(4,4-difluoropiperidin-1-yl)-1,2-benzoxazole-3-carboxylate (310.0 mg) as a yellow solid. LCMS Method A-1: [M+H]+= 297
310 mg With methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II); caesium carbonate In 1,4-dioxane at 20℃; Inert atmosphere; Step 1: methyl 6-(4,4-difluoropiperidin-1-yl)-1,2-benzoxazole-3-carboxylate Methyl 6-bromo-1,2-benzoxazole-3-carboxylate (1.0 g, 3.9 mmol, 1.0 equiv.) and 4,4-difluoropiperidine (473.1 mg, 3.9 mmol, 1.0 equiv.) were dissolved in 1,4-dioxane (8 mL), then Xphos Pd G3 (330.6 mg, 0.4 mmol, 0.1 equiv.) and Cs2CO3(3.8 g, 11.7 mmol, 3.0 equiv.) were added under an atmosphere of nitrogen. The reaction mixture was stirred overnight at ambient temperature and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel, eluting with ethyl acetate/petroleum ether (1:2) to give methyl 6-(4,4-difluoropiperidin-1-yl)-1,2-benzoxazole-3-carboxylate (310.0 mg) as a yellow solid. LCMS Method A-1: [M+H]+= 297
  • 33
  • [ 21987-29-1 ]
  • [ 1123169-23-2 ]
  • [ 2758682-21-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II); caesium carbonate / 1,4-dioxane / 20 °C / Inert atmosphere 2: lithium hydroxide; water / methanol / 20 °C
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 1123169-23-2 ]

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Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate

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Esters

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Related Parent Nucleus of
[ 1123169-23-2 ]

Benzisoxazoles

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Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate

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Chemical Structure| 57764-50-8

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Ethyl 6-hydroxybenzo[d]isoxazole-3-carboxylate

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