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Inaccessible (Haz class 6.1), Domestic | USD 41.00 |
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CAS No. : | 1544739-25-4 | MDL No. : | MFCD23098825 |
Formula : | C13H17BBrFO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 314.99 g/mol | Pubchem ID : | - |
Synonyms : |
|
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P201-P202-P261-P264-P270-P271-P280-P302+P352-P304+P340-P308+P313-P310-P330-P361-P403+P233-P405-P501 | UN#: | 1759 |
Hazard Statements: | H302-H314 | Packing Group: | Ⅲ |
GHS Pictogram: |
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Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With silver carbonate In toluene at 110℃; Inert atmosphere; | 2-4.C Step C: 4- [2-Fluoro-5 -(4,4,5,5 -tetramethyl- [1,3,21 dioxaborolan-2-yl)-benzyloxyl -1,1 a,6,6a- tetrahydro-3-aza -cyclopropa[alindene-1-carboxylic acid ethyl ester (2-4) Step C: 4- [2-Fluoro-5 -(4,4,5,5 -tetramethyl- [1,3,21 dioxaborolan-2-yl)-benzyloxyl -1,1 a,6,6a- tetrahydro-3-aza -cyclopropa[alindene-1-carboxylic acid ethyl ester (2-4)To a stirred solution of compound 2-3 (863 mg, 2.74 mmol) and 1-9 (500 mg, 2.28 mmol) intoluene (35 mL), was added Ag2CO3 (1.30 g, 4.56 mmol) in one portion. The resulting mixture was heated to 110°C under N2 protection overnight. TLC showed compound 2-3 was consumed.The mixture was filtered, the filtrate was concentrated to afford crude product which waspurified b by column chromatography on silica gel (PE:EA=5:1) to give 2-4. MS (ESI) mlz: 454 (M+Hj. ‘H-NMR (400 MHz, CDC13) ö: 8.10 (s, 1H), 7.93 (d, 1H, J4.0 Hz), 7.72 (t, 1H, J4.0 Hz), 7.06 (t, 1H, J=2.8 Hz), 6.61 (s, 1H), 5.36 (s, 2H), 4.12 (dd, 2H, J=2.0 and 7.2 Hz), 3.23 (dd, 1H, J=6.0 and 12.0 Hz), 2.98 (d, 1H, J=8.8 Hz), 2.88 (d, 1H, J2.8 Hz), 2.43-2.39 (m, 1H), 1.33(s, 12H), 1.26-1.23 (m, 4H). | |
With silver carbonate In toluene at 110℃; Inert atmosphere; | 2.4.C Step C: 4-[2-Fluoro-5-( 4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyloxy]-L 1a,6,6atetrahydro-3-aza -cyclopropa[a]indene-1-carboxylic acid ethyl ester (2-4) To a stirred solution of compound 2-3 (863 mg, 2.74 mmol) and 1-9 (500 mg, 2.28 mmol) intoluene (35 mL), was added Ag2C03 (1.30 g, 4.56 mmol) in one portion. The resulting mixturewas heated to 11 0°C under N2 protection overnight. TLC showed compound 2-3 was consumed.5 The mixture was filtered, the filtrate was concentrated to afford crude product which was purifiedb by column chromatography on silica gel (PE:EA=5: 1) to give 2-4. MS (ESI) m/z: 454 (M+H+).1H-NMR (400 MHz, CDCh) 8: 8.10 (s, 1H), 7.93 (d, 1H, J=4.0 Hz), 7.72 (t, 1H, J=4.0 Hz),7.06 (t, 1H, J=2.8 Hz), 6.61 (s, 1H), 5.36 (s, 2H), 4.12 (dd, 2H, J=2.0 and 7.2 Hz), 3.23 (dd, 1H,J=6.0 and 12.0 Hz), 2.98 (d, 1H, J=8.8 Hz), 2.88 (d, 1H, J=2.8 Hz), 2.43-2.39 (m, 1H), 1.33 (s,10 12H), 1.26-1.23 (m, 4H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 110 °C / Inert atmosphere 2: phosphorus tribromide / tetrahydrofuran / 1 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With phosphorus tribromide In tetrahydrofuran at 0℃; for 1h; | 2-4.B Step B: 2-(3 -Bromomethyl-4-fluoro-phenyl)-4,4,5 ,5 -tetramethyl- [1,3 ,2ldioxaborolane (2-3) Step B: 2-(3 -Bromomethyl-4-fluoro-phenyl)-4,4,5 ,5 -tetramethyl- [1,3 ,2ldioxaborolane (2-3)To a stirred solution of compound 2-2 (7 g, 28 mmol) in THF (80 mL), was added PBr3 (7.6 g,28 mmol) dropwise at 0 °C. The resulting mixture was stirred at 0 °C for lh. H20 (50 mL) was added to the mixture and the resulting mixture was extracted with EtOAc (50 mL x 3). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to afford crude product, which was purified b by column chromatography on silica gel (PE:EA=20: 1) to give compound 2-3. MS (ESI) mlz: 315, 316 (M+Hj. | |
With phosphorus tribromide In tetrahydrofuran at 0℃; for 1h; | 2.4.B Step B: 2-(3-Bromomethyl-4-fluoro-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (2-3) To a stirred solution of compound 2-2 (7 g, 28 mmol) in THF (80 mL), was added PBr3 (7.6 g,15 28 mmol) dropwise at 0 °C. The resulting mixture was stirred at 0 °C for 1h. H20 (50 mL) wasadded to the mixture and the resulting mixture was extracted with EtOAc (50 mL x 3). Thecombined organic layers were washed with brine, dried over Na2S04, and concentrated to affordcrude product, which was purified b by column chromatography on silica gel (PE:EA=20:1) togive compound 2-3. MS (ESI) m/z: 315, 316 (M+H+). | |
With bromine; triethylamine; triphenylphosphine In dichloromethane at 0 - 20℃; Inert atmosphere; | 55.A Step A. 2-(3-(bromomethyl)-4-fluorophenyl)-4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolane Step A. 2-(3-(bromomethyl)-4-fluorophenyl)-4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolane A methylene chloride solution of bromine (0.698 M, 3 ml, 2.094 mmol) was added slowly to a solution of (2-fluoro-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl)methanol (250 mg, 0.992 mmol), triethylamine (0.15 ml, 1.076 mmol) and triphenylphosphine (547 mg, 2.086 mmol) in dichloromethane (2 ml) at 0°C under N2- The mixture was stirred at RT overnight. The solvent was evaporated. The residue was purified on silica gel using hexane and EtOAc to obtain the title compound. -NMR (500 MHz, CDCI3) δ: 7.84 (dd, 1H), 7.75 (ddd, 1H), 7.06 (dd, 1H), 4.5 (s, 3H), 1.34 (s, 12H). |
With bromine; triethylamine; triphenylphosphine In dichloromethane at 0 - 20℃; Inert atmosphere; | 55.A Step A. 2-(3-(bromomethyl)-4-fluorophenyl)-4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolane Step A. 2-(3-(bromomethyl)-4-fluorophenyl)-4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolane A methylene chloride solution of bromine (0.698 M, 3 ml, 2.094 mmol) was added slowly to a solution of (2-fluoro-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl)methanol (250 mg, 0.992 mmol), triethylamine (0.15 ml, 1.076 mmol) and triphenylphosphine (547 mg, 2.086 mmol) in dichloromethane (2 ml) at 0°C under N2- The mixture was stirred at RT overnight. The solvent was evaporated. The residue was purified on silica gel using hexane and EtOAc to obtain the title compound. -NMR (500 MHz, CDCI3) δ: 7.84 (dd, 1H), 7.75 (ddd, 1H), 7.06 (dd, 1H), 4.5 (s, 3H), 1.34 (s, 12H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: potassium carbonate; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine / water; 1,4-dioxane / 0.17 h / 130 °C / Inert atmosphere; Microwave irradiation | ||
Multi-step reaction with 2 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: potassium carbonate; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine / water; 1,4-dioxane / 0.17 h / 130 °C / Inert atmosphere; Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: potassium carbonate; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine / water; 1,4-dioxane / 0.17 h / 130 °C / Inert atmosphere; Microwave irradiation 3: sodium hydroxide; water / methanol / 0.5 h / 50 °C | ||
Multi-step reaction with 3 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: potassium carbonate; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine / water; 1,4-dioxane / 0.17 h / 130 °C / Inert atmosphere; Microwave irradiation 3: water; sodium hydroxide / methanol / 0.5 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / tetrahydrofuran; water / 0.5 h / 100 °C / Microwave irradiation | ||
Multi-step reaction with 2 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / tetrahydrofuran; water / 0.5 h / 100 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / tetrahydrofuran; water / 0.5 h / 100 °C / Microwave irradiation 3: water; lithium hydroxide / methanol / 1 h / 20 °C | ||
Multi-step reaction with 3 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / tetrahydrofuran; water / 0.5 h / 100 °C / Microwave irradiation 3: water; lithium hydroxide / methanol / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: potassium carbonate; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine / water; 1,4-dioxane / 1 h / Reflux | ||
Multi-step reaction with 2 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: potassium carbonate; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine / water; 1,4-dioxane / 1 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: potassium carbonate; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine / water; 1,4-dioxane / 1 h / Reflux 3: lithium hydroxide monohydrate; water / methanol / 2 h / 40 °C | ||
Multi-step reaction with 3 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: potassium carbonate; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine / water; 1,4-dioxane / 1 h / Reflux 3: water; lithium hydroxide monohydrate / methanol / 2 h / 40 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / tetrahydrofuran; water / 0.17 h / 100 °C / Inert atmosphere; Sealed tube; Microwave irradiation | ||
Multi-step reaction with 2 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / tetrahydrofuran; water / 0.17 h / 100 °C / Inert atmosphere; Sealed tube; Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / tetrahydrofuran; water / 0.17 h / 100 °C / Inert atmosphere; Sealed tube; Microwave irradiation 3: lithium hydroxide monohydrate; water / tetrahydrofuran; methanol / 4 h / 20 °C | ||
Multi-step reaction with 3 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / tetrahydrofuran; water / 0.17 h / 100 °C / Inert atmosphere; Sealed tube; Microwave irradiation 3: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 4 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / tetrahydrofuran; water / 2 h / 100 °C | ||
Multi-step reaction with 2 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / tetrahydrofuran; water / 2 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / tetrahydrofuran; water / 2 h / 100 °C 3: lithium hydroxide monohydrate; water / tetrahydrofuran; methanol / 4 h / 20 °C | ||
Multi-step reaction with 3 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / tetrahydrofuran; water / 2 h / 100 °C 3: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 4 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / tetrahydrofuran; water / 0.5 h / 100 °C / Inert atmosphere; Microwave irradiation | ||
Multi-step reaction with 2 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / tetrahydrofuran; water / 0.5 h / 100 °C / Inert atmosphere; Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / tetrahydrofuran; water / 0.5 h / 100 °C / Inert atmosphere; Microwave irradiation 3: water; lithium hydroxide / tetrahydrofuran; methanol / 5 h / 20 °C | ||
Multi-step reaction with 3 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / tetrahydrofuran; water / 0.5 h / 100 °C / Inert atmosphere; Microwave irradiation 3: water; lithium hydroxide / tetrahydrofuran; methanol / 5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: dmap; copper diacetate / acetonitrile / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: dmap; copper diacetate / acetonitrile / 80 °C / Inert atmosphere 3: sodium hydroxide; water / tetrahydrofuran; methanol / 3 h / 20 °C | ||
Multi-step reaction with 3 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: dmap; copper diacetate / acetonitrile / 80 °C / Inert atmosphere 3: water; sodium hydroxide / tetrahydrofuran; methanol / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 100 °C | ||
Multi-step reaction with 2 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate / water; 1,4-dioxane / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 100 °C 3: water; lithium hydroxide / tetrahydrofuran; ethanol / 20 °C | ||
Multi-step reaction with 3 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate / water; 1,4-dioxane / 100 °C 3: water; lithium hydroxide / tetrahydrofuran; ethanol / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 100 °C / Inert atmosphere 3: water; sodium hydroxide / methanol / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: potassium carbonate; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine / water; 1,4-dioxane / 0.17 h / 100 °C / Inert atmosphere; Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: silver carbonate / toluene / 110 °C / Inert atmosphere 2: potassium carbonate; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine / water; 1,4-dioxane / 0.17 h / 100 °C / Inert atmosphere; Microwave irradiation 3: water; lithium hydroxide / methanol / 20 °C |
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