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[ CAS No. 1025718-78-8 ]

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Chemical Structure| 1025718-78-8
Chemical Structure| 1025718-78-8
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Product Details of [ 1025718-78-8 ]

CAS No. :1025718-78-8 MDL No. :MFCD12405334
Formula : C14H18BBrO4 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :341.01 g/mol Pubchem ID :-
Synonyms :

Safety of [ 1025718-78-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1025718-78-8 ]

  • Downstream synthetic route of [ 1025718-78-8 ]

[ 1025718-78-8 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 1025718-78-8 ]
  • [ 192810-12-1 ]
YieldReaction ConditionsOperation in experiment
With Oxone In acetone at 25℃; for 0.133333h;
Stage #1: methyl 3-bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate With Oxone; water In acetone at 20℃; for 0.133333h; Stage #2: With sodium hydrogensulfite In water; acetone 160.a 0528] a) 3-Bromo-5-hydroxy-benzoic acid methyl ester. A 5 mL tube was charged with 3,5-dibromo-benzoic acid methyl ester (586 mg, 2.0 mmol), bis(pinacolato)diboron (254 mg, 1.0 mmol), potassium acetate (294 mg, 3.0 mmol) and PdCl2(dppf) complex (50 mg). DMSO (3 mL) was added, and the solution was degassed with nitrogen, then the tube was sealed. After heating the tube for 16 h at 8O0C, the mixture was diluted with ethyl acetate (10 mL) and extracted with brine (10 mL, three times), and saturated aqueous sodium bicarbonate (5 mL), and the organic layer was dried and concentrated to give 3-bromo-5-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester. To a solution of this material in acetone (4 mL) was added an aqueous solution of Oxone (2 KHSO5-KHSO4-K2SO4) (1.23 g in 5 mL water), and the reaction mixture was stirred vigorously for 8 min at room temperature. The reaction mixture was quenched with aqueous sodium hydrogensulfite. The brown solution was extracted with ethyl acetate, and the organic layer was extracted with brine and water, dried and concentrated. The residue was passed through a short silica gel column using a gradient of methylene chloride to 2% methanol in methylene chloride as an eluent to give 104 mg of 3-bromo-5-hydroxy-benzoic acid methyl ester.
  • 2
  • [ 51329-15-8 ]
  • [ 73183-34-3 ]
  • [ 1025718-78-8 ]
YieldReaction ConditionsOperation in experiment
With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In dimethyl sulfoxide; at 80℃; for 16h; a) 3-Bromo-5-hydroxy-benzoic acid methyl ester. A 5 mL tube was charged with <strong>[51329-15-8]3,5-dibromo-benzoic acid methyl ester</strong> (586 mg, 2.0 mmol), bis(pinacolato)diboron (254 mg, 1.0 mmol), potassium acetate (294 mg, 3.0 mmol) and PdCl2(dppf) complex (50 mg). DMSO (3 mL) was added, and the solution was degassed with nitrogen, then the tube was sealed. After heating the tube for 16 h at 80 C., the mixture was diluted with ethyl acetate (10 mL) and extracted with brine (10 mL, three times), and saturated aqueous sodium bicarbonate (5 mL), and the organic layer was dried and concentrated to give 3-bromo-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester. To a solution of this material in acetone (4 mL) was added an aqueous solution of Oxones (2 KHSO5.KHSO4.K2SO4) (1.23 g in 5 mL water), and the reaction mixture was stirred vigorously for 8 min at room temperature. The reaction mixture was quenched with aqueous sodium hydrogensulfite. The brown solution was extracted with ethyl acetate, and the organic layer was extracted with brine and water, dried and concentrated. The residue was passed through a short silica gel column using a gradient of methylene chloride to 2% methanol in methylene chloride as an eluent to give 104 mg of 3-bromo-5-hydroxy-benzoic acid methyl ester.
With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In dimethyl sulfoxide; at 80℃; for 16h;Sealed tube; 0528] a) 3-Bromo-5-hydroxy-benzoic acid methyl ester. A 5 mL tube was charged with <strong>[51329-15-8]3,5-dibromo-benzoic acid methyl ester</strong> (586 mg, 2.0 mmol), bis(pinacolato)diboron (254 mg, 1.0 mmol), potassium acetate (294 mg, 3.0 mmol) and PdCl2(dppf) complex (50 mg). DMSO (3 mL) was added, and the solution was degassed with nitrogen, then the tube was sealed. After heating the tube for 16 h at 8O0C, the mixture was diluted with ethyl acetate (10 mL) <n="185"/>and extracted with brine (10 mL, three times), and saturated aqueous sodium bicarbonate (5 mL), and the organic layer was dried and concentrated to give 3-bromo-5-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester. To a solution of this material in acetone (4 mL) was added an aqueous solution of Oxone (2 KHSO5-KHSO4-K2SO4) (1.23 g in 5 mL water), and the reaction mixture was stirred vigorously for 8 min at room temperature. The reaction mixture was quenched with aqueous sodium hydrogensulfite. The brown solution was extracted with ethyl acetate, and the organic layer was extracted with brine and water, dried and concentrated. The residue was passed through a short silica gel column using a gradient of methylene chloride to 2% methanol in methylene chloride as an eluent to give 104 mg of 3-bromo-5-hydroxy-benzoic acid methyl ester.
  • 3
  • [ 1025718-78-8 ]
  • [ 905917-51-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aq. Oxone / acetone / 0.13 h / 25 °C
  • 4
  • [ 1025718-78-8 ]
  • 1-(5-hydroxy-3'-methyl-biphenyl-3-yl)-ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aq. Oxone / acetone / 0.13 h / 25 °C
  • 5
  • [ 1025718-78-8 ]
  • 1-(3-hydroxy-5-pyridin-3-ylethynyl-phenyl)ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aq. Oxone / acetone / 0.13 h / 25 °C
  • 6
  • [ 1025718-78-8 ]
  • 3-hydroxy-5-phenylamino-N-pyridin-3-yl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aq. Oxone / acetone / 0.13 h / 25 °C
  • 7
  • [ 1025718-78-8 ]
  • 3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-hydroxy-N-(pyridin-3-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aq. Oxone / acetone / 0.13 h / 25 °C
  • 8
  • [ 188813-07-2 ]
  • [ 73183-34-3 ]
  • [ 1025718-78-8 ]
YieldReaction ConditionsOperation in experiment
85% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃;
74% With potassium polysulfide; water; N,N,N',N'-tetramethylguanidine In acetonitrile at 30℃; for 5h; Irradiation; Inert atmosphere; Sealed tube;
With potassium acetate In dimethyl sulfoxide at 80℃; for 20h; 9.1 Step 1 3-Bromo-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic Acid Methyl Ester; 3-Bromo-5-iodo-benzoic acid methyl ester (14.16 g, 41.53 mmol), bis(pinacolato)-diborane (11.60 g, 45.7 mmol), PdCl2(dppf)2 (1.02 g, 1.256 mmol) and potassium acetate (12.22 g, 124.6 mmol) were added to 50 mL of DMSO, and the reaction mixture was stirred at 80° C. for 20 hours, then cooled to room temperature. The reaction mixture was diluted with water and extracted with diethyl ether. The combined organic extracts were dried over MgSO4, filtered, and concentrated under reduced pressure to give 18.5 g of 3-bromo-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester, which was used directly in the next step without further purification.
With potassium acetate In dimethyl sulfoxide at 80℃; for 20h; 8.1 Step 1 3-Bromo-5-(4,4,5,5-tetramethyl-[3,2]dioxaborolan-2-yl)-benzoic Acid Methyl Ester; 3-Bromo-5-iodo-benzoic acid methyl ester (14.16 g, 41.53 mmol), bis(pinacolato)-diborane (11.60 g, 45.7 mmol), PdCl2(dppf)2 (1.02 g, 1.256 mmol) and potassium acetate (12.22 g, 124.6 mmol) were added to 50 mL of DMSO, and the reaction mixture was stirred at 80° C. for 20 hours, then cooled to room temperature. The reaction mixture was diluted with water and extracted with diethyl ether. The combined organic extracts were dried over Mg SO4, filtered, and concentrated under reduced pressure to give 18.5 g of 3-bromo-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester, which was used directly in the next step without further purification.
With potassium acetate In dimethyl sulfoxide at 80℃; for 20h; 9.1 Step 1 3-Bromo-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic Acid Methyl Ester 3-Bromo-5-iodo-benzoic acid methyl ester (14.16 g, 41.53 mmol), bis(pinacolato)-diborane (11.60 g, 45.7 mmol), PdCl2(dppf)2 (1.02 g, 1.256 mmol) and potassium acetate (12.22 g, 124.6 mmol) were added to 50 mL of DMSO, and the reaction mixture was stirred at 80° C. for 20 hours, then cooled to room temperature. The reaction mixture was diluted with water and extracted with diethyl ether. The combined organic extracts were dried over Mg SO4, filtered, and concentrated under reduced pressure to give 18.5 g of 3-bromo-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester, which was used directly in the next step without further purification.
With potassium acetate In dimethyl sulfoxide at 80℃; for 20h; 8.1 Step 1 3-Bromo-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester 3-Bromo-5-iodo-benzoic acid methyl ester (14.16 g, 41.53 mmol), bis(pinacolato)-diborane (11.60 g, 45.7 mmol), PdCl2(dppf)2 (1.02 g, 1.256 mmol) and potassium acetate (12.22 g, 124.6 mmol) were added to 50 mL of DMSO, and the reaction mixture was stirred at 80° C. for 20 hours, then cooled to room temperature. The reaction mixture was diluted with water and extracted with diethyl ether. The combined organic extracts were dried over Mg SO4, filtered, and concentrated under reduced pressure to give 18.5 g of 3-bromo-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester, which was used directly in the next step without further purification.
With potassium acetate In 1,4-dioxane at 80℃; for 42h; 4.539.B Step B: methyl 3-bromo-5-(4A5.5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzoate; To a solution of methyl 3-bromo-5-iodobenzoate (2.06 g. 6.04 mmol) in dioxane (40 mL) were added bis(pinacolato)diboron (1.92 g, 7.55 mmol), potassium acetate (1.19 g, 12.1 mmol) and dichloro[l,l'-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (0.22 g, 0.30 mmol). The mixture was degassed with argon and stirred at 80 0C. After 42 h, the mixture was cooled to ambient temperature and filtered through Celite. The filtered cake was washed with ethyl acetate and the filtrate was concentrated. Purification by silica gel chromatography (100% hexanes - * 50% hexanes / ethyl acetate) gave the title compound (1.74 g). MS 341.0 (M).
With potassium acetate In dimethyl sulfoxide at 80℃; for 20h; 8.1 Step 1 3-Bromo-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester 3-Bromo-5-iodo-benzoic acid methyl ester (14.16 g, 41.53 mmol), bis(pinacolato)-diborane (11.60 g, 45.7 mmol), PdCl2(dppf)2 (1.02 g, 1.256 mmol) and potassium acetate (12.22 g, 124.6 mmol) were added to 50 mL of DMSO, and the reaction mixture was stirred at 80° C. for 20 hours, then cooled to room temperature. The reaction mixture was diluted with water and extracted with diethyl ether. The combined organic extracts were dried over MgSO4, filtered, and concentrated under reduced pressure to give 18.5 g of 3-bromo-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester, which was used directly in the next step without further purification.
With potassium acetate In dimethyl sulfoxide at 80℃; for 20h; 6.1 Step 1 3-Bromo-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester3-Bromo-5-iodo-benzoic acid methyl ester (14.16 g, 41.53 mmol), bis(pinacolato)-diborane (11.60 g, 45.7 mmol), PdCl2(dppf)2 (1.02 g, 1.256 mmol) and potassium acetate (12.22 g, 124.6 mmol) were addded to 50 mL of DMSO, and the reaction mixture was stirred at 80° C. for 20 hours, then cooled to room temperature. The reaction mixture was diluted with water and extracted with diethyl ether. The combined organic extracts were dried over Mg SO4, filtered, and concentrated under reduced pressure to give 18.5 g of 3-bromo-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester, which was used directly in the next step without further purification.

Reference: [1]Ginnetti, Anthony T.; Paone, Daniel V.; Stauffer, Shaun R.; Potteiger, Craig M.; Shaw, Anthony W.; Deng, James; Mulhearn, James J.; Nguyen, Diem N.; Segerdell, Carolyn; Anquandah, Juliana; Calamari, Amy; Cheng, Gong; Leitl, Michael D.; Liang, Annie; Moore, Eric; Panigel, Jacqueline; Urban, Mark; Wang, Jixin; Fillgrove, Kerry; Tang, Cuyue; Cook, Sean; Kane, Stefanie; Salvatore, Christopher A.; Graham, Samuel L.; Burgey, Christopher S. [Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 8, p. 1392 - 1396]
[2]Li, Haoyu; Tang, Xinxin; Pang, Jia Hao; Wu, Xiangyang; Yeow, Edwin K. L.; Wu, Jie; Chiba, Shunsuke [Journal of the American Chemical Society, 2021, vol. 143, # 1, p. 481 - 487]
[3]Current Patent Assignee: ROCHE HOLDING AG - US2009/163502, 2009, A1 Location in patent: Page/Page column 42
[4]Current Patent Assignee: ROCHE HOLDING AG - US2009/163499, 2009, A1 Location in patent: Page/Page column 33
[5]Current Patent Assignee: ROCHE HOLDING AG - US2009/170873, 2009, A1 Location in patent: Page/Page column 47-48
[6]Current Patent Assignee: ROCHE HOLDING AG - US2009/170874, 2009, A1 Location in patent: Page/Page column 63
[7]Current Patent Assignee: MERCK &amp; CO INC - WO2009/58298, 2009, A1 Location in patent: Page/Page column 175
[8]Current Patent Assignee: ROCHE HOLDING AG - US2010/152203, 2010, A1 Location in patent: Page/Page column 23
[9]Current Patent Assignee: ROCHE HOLDING AG - US2010/324069, 2010, A1 Location in patent: Page/Page column 27-28
  • 9
  • [ 1025718-78-8 ]
  • [ 3510-66-5 ]
  • [ 1149752-92-0 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate In 1,2-dimethoxyethane; water for 8h; Heating / reflux; 9.2 Step 2 3-Bromo-5-(5-methyl-pyridin-2-yl)-benzoic Acid Methyl Ester; A mixture of 2-bromo-5-methyl-pyridine (10.27 g, 59.68 mmol) and palladium tetrakis(triphenylphosphine) (1.88 g, 1.65 mmol) in 300 mL DME was stirred at 60° C. under nitrogen for 30 minutes. To this mixture was added 3-bromo-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (18.5 g, 54.25 mmol), followed by K3PO4 23.03 g, 108.5 mmol) in 40 mL water. The mixture was refluxed for eight hours, then cooled to room temperature and partitioned between water and EtOAc. The combined organic layers were washed with water, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified via flash chromatography (5:1 EtOAc/hexanes) to give 8.5 g of 3-bromo-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester, MS (M+H)=306.
With potassium phosphate In 1,2-dimethoxyethane; water for 8h; Heating / reflux; 8.2 Step 2 3-Bromo-5-(5-methyl-pyridin-2-yl)-benzoic Acid Methyl Ester; A mixture of 2-bromo-5-methyl-pyridine (10.27 g, 59.68 mmol) and palladium tetrakis(triphenylphosphine) (1.88 g, 1.65 mmol) in 300 mL DME was stirred at 60° C. under nitrogen for 30 minutes. To this mixture was added 3-bromo-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (18.5 g, 54.25 mmol), followed by K3PO4 23.03 g, 108.5 mmol) in 40 mL water. The mixture was refluxed for eight hours, then cooled to room temperature and partitioned between water and EtOAc. The combined organic layers were washed with water, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified via flash chromatography (5:1 EtOAc/hexanes) to give 8.5 g of 3-bromo-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester, MS (M+H)=306.
Stage #1: 2-Bromo-5-methylpyridine In 1,2-dimethoxyethane at 60℃; for 0.5h; Stage #2: methyl 3-bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate With potassium phosphate In 1,2-dimethoxyethane; water for 8h; Heating / reflux; 9.2 A mixture of 2-bromo-5-methyl-pyridine (10.27 g, 59.68 mmol) and palladium tetrakis(triphenylphosphine) (1.88 g, 1.65 mmol) in 300 mL DME was stirred at 60° C. under nitrogen for 30 minutes. To this mixture was added 3-bromo-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (18.5 g, 54.25 mmol), followed by K3PO4 23.03 g, 108.5 mmol) in 40 mL water. The mixture was refluxed for eight hours, then cooled to room temperature and partitioned between water and EtOAc. The combined organic layers were washed with water, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified via flash chromatography (5:1 EtOAc/hexanes) to give 8.5 g of 3-bromo-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester, MS (M+H)=306.
Stage #1: methyl 3-bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate; 2-Bromo-5-methylpyridine With potassium phosphate In 1,2-dimethoxyethane; water for 8h; Heating / reflux; Stage #2: methyl 3-bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate With potassium phosphate In 1,2-dimethoxyethane; water for 8h; Heating / reflux; 8.2 Step 2 3-Bromo-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl esterA mixture of 2-bromo-5-methyl-pyridine (10.27 g, 59.68 mmol) and palladium tetrakis(triphenylphosphine) (1.88 g, 1.65 mmol) in 300 mL DME was stirred at 60° C. under nitrogen for 30 minutes. To this mixture was added 3-bromo-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (18.5 g, 54.25 mmol), followed by K3PO4 23.03 g, 108.5 mmol) in 40 mL water. The mixture was refluxed for eight hours, then cooled to room temperature and partitioned between water and EtOAc. The combined organic layers were washed with water, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified via flash chromatography (5:1 EtOAc/hexanes) to give 8.5 g of 3-bromo-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester, MS (M+H)=306.
With potassium phosphate In 1,2-dimethoxyethane; water at 60℃; for 8.5h; Inert atmosphere; Reflux; 8.2 A mixture of 2-bromo-5-methyl-pyridine (10.27 g, 59.68 mmol) and palladium tetrakis(triphenylphosphine) (1.88 g, 1.65 mmol) in 300 mL DME was stirred at 60° C. under nitrogen for 30 minutes. To this mixture was added 3-bromo-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (18.5 g, 54.25 mmol), followed by K3PO4 23.03 g, 108.5 mmol) in 40 mL water. The mixture was refluxed for eight hours, then cooled to room temperature and partitioned between water and EtOAc. The combined organic layers were washed with water, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified via flash chromatography (5:1 EtOAc/hexanes) to give 8.5 g of 3-bromo-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester, MS (M+H)=306.
With potassium phosphate In 1,2-dimethoxyethane; water for 8h; Reflux; Inert atmosphere; 6.2 Step 2 3-Bromo-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl esterA mixture of 2-bromo-5-methyl-pyridine (10.27 g, 59.68 mmol) and palladium tetrakis(triphenylphosphine) (1.88 g, 1.65 mmol) in 300 mL DME was stirred at 60° C. under nitrogen for 30 minutes. To this mixture was added 3-bromo-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (18.5 g, 54.25 mmol), followed by K3PO4 23.03 g, 108.5 mmol) in 40 mL water. The mixture was refluxed for eight hours, then cooled to room temperature and partitioned between water and EtOAc. The combined organic layers were washed with water, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified via flash chromatography (5:1 EtOAc/hexanes) to give 8.5 g of 3-bromo-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester, MS (M+H)=306.

  • 10
  • [ 1025718-78-8 ]
  • [ 40473-01-6 ]
  • [ 1150263-42-5 ]
YieldReaction ConditionsOperation in experiment
With diisopropylamine;palladium diacetate; trisodium tris(3-sulfophenyl)phosphine; In water; N,N-dimethyl-formamide; at 80℃; for 1h; Step C: methyl 3-bromo-5-(5-chloropyridin-2-yl')benzoate; To a solution of methyl 3-bromo-5-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)benzoate (0.10 g, 0.29 mmol) in DMF (1.5 mL) and water (0.49 mL) were added <strong>[40473-01-6]2-bromo-5-chloropyridine</strong> (0.17 g, 0.88 mmol), palladium(II) aceate (3.3 mg, 0.015 mmol), 3,3'3"-phosphinidynetris(benzenesulfonic acid) trisodium salt (25.0 mg, 0.044 mmol) and diisopropylamine (0.10 mL, 0.73 mmol). The mixture was heated to 80 C. After 1 h, the mixture was filtered and the filtrate was purified by reverse phase chromatography (C-18, 85% <n="177"/>water / acetonitrile ? 5% water / acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (78 mg). MS 326.0 (M).
  • 11
  • [ 618-89-3 ]
  • [ 73183-34-3 ]
  • [ 1025718-78-8 ]
YieldReaction ConditionsOperation in experiment
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In hexane at 20℃; Inert atmosphere;
Stage #1: bis(pinacol)diborane With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran for 0.0333333h; Inert atmosphere; Sonication; Stage #2: methyl 3-bromobenzoate In tetrahydrofuran at 80℃; for 24h; Inert atmosphere;
With (1,5-cyclooctadiene)(methoxy)iridium(l) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran at 80℃; for 24h; Inert atmosphere;
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In hexane at 20℃; regioselective reaction;

  • 12
  • [ 1025718-78-8 ]
  • [ 1620809-35-9 ]
YieldReaction ConditionsOperation in experiment
With potassium fluoride; trimethylsilylazide; copper(l) chloride In methanol at 20 - 70℃;
With potassium fluoride; t-butyl azide; copper(l) chloride In methanol Reflux;
  • 13
  • [ 1025718-78-8 ]
  • [ 1620809-40-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: trimethylsilylazide; copper(l) chloride; potassium fluoride / methanol / 20 - 70 °C 2: diisobutylaluminium hydride / hexane; tetrahydrofuran / 3 h / -78 °C / Inert atmosphere 3: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 20 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: copper(l) chloride; potassium fluoride; t-butyl azide / methanol / Reflux 2: diisobutylaluminium hydride / tetrahydrofuran / 3 h / -78 °C 3: 1,8-diazabicyclo[5.4.0]undec-7-ene; diphenyl phosphoryl azide / toluene / 20 °C
  • 14
  • [ 1025718-78-8 ]
  • 2-methyl-2-(5-methylhex-4-en-2-yn-1-yl)cyclopentane-1,3-dione [ No CAS ]
  • (±)-3-[(3aR,7R,7aR)-7a-hydroxy-3a-methyl-3-oxo-7-(prop-1-en-2-yl)-2,3,3a,4,7,7a-hexahydro-1H-inden-5-yl]-5-bromobenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With potassium phosphate; chloro(1,5-cyclooctadiene)rhodium(I) dimer In methanol; tert-butyl methyl ether at 65℃; for 16h; Microwave irradiation; Inert atmosphere; Sealed tube; diastereoselective reaction;
  • 15
  • [ 1025718-78-8 ]
  • [ 1150260-61-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: palladium diacetate; trisodium tris(3-sulfophenyl)phosphine; diisopropylamine / N,N-dimethyl-formamide; water / 80 °C 2: palladium diacetate; trisodium tris(3-sulfophenyl)phosphine; diisopropylamine / N,N-dimethyl-formamide; water / 80 °C 3: water; sodium hydroxide / methanol 4: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; diethylamine / N,N-dimethyl-formamide / 20 °C
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