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CAS No. : | 1025718-78-8 | MDL No. : | MFCD12405334 |
Formula : | C14H18BBrO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YTLNMWYKZKGCOV-UHFFFAOYSA-N |
M.W : | 341.01 | Pubchem ID : | 53436914 |
Synonyms : |
|
Num. heavy atoms : | 20 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 81.9 |
TPSA : | 44.76 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.93 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 3.45 |
Log Po/w (WLOGP) : | 2.53 |
Log Po/w (MLOGP) : | 2.19 |
Log Po/w (SILICOS-IT) : | 2.46 |
Consensus Log Po/w : | 2.13 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.15 |
Solubility : | 0.024 mg/ml ; 0.0000705 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.07 |
Solubility : | 0.0289 mg/ml ; 0.0000849 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -4.89 |
Solubility : | 0.00438 mg/ml ; 0.0000129 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 3.14 |
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: |
* 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.
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: aq. Oxone / acetone / 0.13 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: aq. Oxone / acetone / 0.13 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: aq. Oxone / acetone / 0.13 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: aq. Oxone / acetone / 0.13 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: aq. Oxone / acetone / 0.13 h / 25 °C |
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation 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). |
Yield | Reaction Conditions | Operation 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; |
Yield | Reaction Conditions | Operation 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; |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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; |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 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 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 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 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.15 g | With 1,10-Phenanthroline; copper diacetate In N,N-dimethyl-formamide at 20℃; for 12h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sulfuric acid / 20 h / Reflux 2: diethyl ether / 1.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In diethyl ether at 20℃; for 1.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 14h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 0 - 20 °C 2: 1H-imidazole; dmap / N,N-dimethyl-formamide / 21 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 0 - 20 °C 2: 1H-imidazole; dmap / N,N-dimethyl-formamide / 21 h / 20 °C 3: chloro(1,5-cyclooctadiene)rhodium(I) dimer; caesium carbonate; water / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 0 - 20 °C 2: 1H-imidazole; dmap / N,N-dimethyl-formamide / 21 h / 20 °C 3: chloro(1,5-cyclooctadiene)rhodium(I) dimer; caesium carbonate; water / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere 4: boron trichloride methyl sulfide complex / tetrahydrofuran / 2 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 0 - 20 °C 2: 1H-imidazole; dmap / N,N-dimethyl-formamide / 21 h / 20 °C 3: chloro(1,5-cyclooctadiene)rhodium(I) dimer; caesium carbonate; water / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere 4: boron trichloride methyl sulfide complex / tetrahydrofuran / 2 h / Reflux 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 0 - 20 °C 2: 1H-imidazole; dmap / N,N-dimethyl-formamide / 21 h / 20 °C 3: chloro(1,5-cyclooctadiene)rhodium(I) dimer; caesium carbonate; water / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere 4: boron trichloride methyl sulfide complex / tetrahydrofuran / 2 h / Reflux 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 20 °C 6: palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; potassium phosphate / 1,4-dioxane / 20 h / 50 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 0 - 20 °C 2: 1H-imidazole; dmap / N,N-dimethyl-formamide / 21 h / 20 °C 3: chloro(1,5-cyclooctadiene)rhodium(I) dimer; caesium carbonate; water / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere 4: boron trichloride methyl sulfide complex / tetrahydrofuran / 2 h / Reflux 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 20 °C 6: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol / 5.5 h / 90 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 0 - 20 °C 2: 1H-imidazole; dmap / N,N-dimethyl-formamide / 21 h / 20 °C 3: chloro(1,5-cyclooctadiene)rhodium(I) dimer; caesium carbonate; water / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere 4: boron trichloride methyl sulfide complex / tetrahydrofuran / 2 h / Reflux 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 20 °C 6: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol / 5.5 h / 90 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 0 - 20 °C 2: 1H-imidazole; dmap / N,N-dimethyl-formamide / 21 h / 20 °C 3: chloro(1,5-cyclooctadiene)rhodium(I) dimer; caesium carbonate; water / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere 4: boron trichloride methyl sulfide complex / tetrahydrofuran / 2 h / Reflux 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 20 °C 6: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane / 4 h / 95 °C / Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 0 - 20 °C 2: 1H-imidazole; dmap / N,N-dimethyl-formamide / 21 h / 20 °C 3: chloro(1,5-cyclooctadiene)rhodium(I) dimer; caesium carbonate; water / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere 4: boron trichloride methyl sulfide complex / tetrahydrofuran / 2 h / Reflux 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 20 °C 6: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane / 4 h / 95 °C / Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 0 - 20 °C 2: 1H-imidazole; dmap / N,N-dimethyl-formamide / 21 h / 20 °C 3: chloro(1,5-cyclooctadiene)rhodium(I) dimer; caesium carbonate; water / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere 4: boron trichloride methyl sulfide complex / tetrahydrofuran / 2 h / Reflux 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 20 °C 6: palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; potassium phosphate / 1,4-dioxane / 20 h / 50 °C / Inert atmosphere 7: sodium periodate; ruthenium(III) trichloride hydrate / ethyl acetate; acetonitrile / 2 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 0 - 20 °C 2: 1H-imidazole; dmap / N,N-dimethyl-formamide / 21 h / 20 °C 3: chloro(1,5-cyclooctadiene)rhodium(I) dimer; caesium carbonate; water / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere 4: boron trichloride methyl sulfide complex / tetrahydrofuran / 2 h / Reflux 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 20 °C 6: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol / 5.5 h / 90 °C / Inert atmosphere 7: sodium periodate; ruthenium(III) trichloride hydrate / ethyl acetate; acetonitrile; water / 2 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 0 - 20 °C 2: 1H-imidazole; dmap / N,N-dimethyl-formamide / 21 h / 20 °C 3: chloro(1,5-cyclooctadiene)rhodium(I) dimer; caesium carbonate; water / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere 4: boron trichloride methyl sulfide complex / tetrahydrofuran / 2 h / Reflux 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 20 °C 6: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol / 5.5 h / 90 °C / Inert atmosphere 7: sodium periodate; ruthenium(III) trichloride hydrate / ethyl acetate; acetonitrile; water / 2 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 0 - 20 °C 2: 1H-imidazole; dmap / N,N-dimethyl-formamide / 21 h / 20 °C 3: chloro(1,5-cyclooctadiene)rhodium(I) dimer; caesium carbonate; water / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere 4: boron trichloride methyl sulfide complex / tetrahydrofuran / 2 h / Reflux 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 20 °C 6: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane / 4 h / 95 °C / Inert atmosphere; Sealed tube 7: sodium periodate; ruthenium(III) trichloride hydrate / ethyl acetate; acetonitrile; water / 2 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 0 - 20 °C 2: 1H-imidazole; dmap / N,N-dimethyl-formamide / 21 h / 20 °C 3: chloro(1,5-cyclooctadiene)rhodium(I) dimer; caesium carbonate; water / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere 4: boron trichloride methyl sulfide complex / tetrahydrofuran / 2 h / Reflux 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 20 °C 6: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane / 4 h / 95 °C / Inert atmosphere; Sealed tube 7: sodium periodate; ruthenium(III) trichloride hydrate / ethyl acetate; acetonitrile; water / 2 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 0 - 20 °C 2: 1H-imidazole; dmap / N,N-dimethyl-formamide / 21 h / 20 °C 3: chloro(1,5-cyclooctadiene)rhodium(I) dimer; caesium carbonate; water / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere 4: boron trichloride methyl sulfide complex / tetrahydrofuran / 2 h / Reflux 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 20 °C 6: palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; potassium phosphate / 1,4-dioxane / 20 h / 50 °C / Inert atmosphere 7: sodium periodate; ruthenium(III) trichloride hydrate / ethyl acetate; acetonitrile / 2 h / 0 °C 8: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 0 - 20 °C 2: 1H-imidazole; dmap / N,N-dimethyl-formamide / 21 h / 20 °C 3: chloro(1,5-cyclooctadiene)rhodium(I) dimer; caesium carbonate; water / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere 4: boron trichloride methyl sulfide complex / tetrahydrofuran / 2 h / Reflux 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 20 °C 6: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol / 5.5 h / 90 °C / Inert atmosphere 7: sodium periodate; ruthenium(III) trichloride hydrate / ethyl acetate; acetonitrile; water / 2 h / 0 °C 8: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 0 - 20 °C 2: 1H-imidazole; dmap / N,N-dimethyl-formamide / 21 h / 20 °C 3: chloro(1,5-cyclooctadiene)rhodium(I) dimer; caesium carbonate; water / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere 4: boron trichloride methyl sulfide complex / tetrahydrofuran / 2 h / Reflux 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 20 °C 6: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol / 5.5 h / 90 °C / Inert atmosphere 7: sodium periodate; ruthenium(III) trichloride hydrate / ethyl acetate; acetonitrile; water / 2 h / 0 °C 8: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 0 - 20 °C 2: 1H-imidazole; dmap / N,N-dimethyl-formamide / 21 h / 20 °C 3: chloro(1,5-cyclooctadiene)rhodium(I) dimer; caesium carbonate; water / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere 4: boron trichloride methyl sulfide complex / tetrahydrofuran / 2 h / Reflux 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 20 °C 6: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane / 4 h / 95 °C / Inert atmosphere; Sealed tube 7: sodium periodate; ruthenium(III) trichloride hydrate / ethyl acetate; acetonitrile; water / 2 h / 0 °C 8: trifluoroacetic acid / dichloromethane / 2.5 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 0 - 20 °C 2: 1H-imidazole; dmap / N,N-dimethyl-formamide / 21 h / 20 °C 3: chloro(1,5-cyclooctadiene)rhodium(I) dimer; caesium carbonate; water / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere 4: boron trichloride methyl sulfide complex / tetrahydrofuran / 2 h / Reflux 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 20 °C 6: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane / 4 h / 95 °C / Inert atmosphere; Sealed tube 7: sodium periodate; ruthenium(III) trichloride hydrate / ethyl acetate; acetonitrile; water / 2 h / 0 °C 8: boron tribromide / dichloromethane / 2 h / 20 °C |
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