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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Synonyms: 2-Bromopyridine-5-boronic acid
4.5
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| CAS No. : | 223463-14-7 |
| Formula : | C5H5BBrNO2 |
| M.W : | 201.81 |
| SMILES Code : | OB(C1=CN=C(Br)C=C1)O |
| Synonyms : |
2-Bromopyridine-5-boronic acid
|
| English Name : | (6-Bromopyridin-3-yl)boronic acid |
| MDL No. : | MFCD03411558 |
| InChI Key : | BCYWDUVHAPHGIP-UHFFFAOYSA-N |
| Pubchem ID : | 2762706 |
| GHS Pictogram: | |
| Signal Word: | |
| Hazard Statements: | |
| Precautionary Statements: | |
| Class: | |
| UN#: | |
| Packing Group: |
* 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 tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In 1,2-dimethoxyethane at 80℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 85% | With caesium carbonate In methanol; water; toluene Heating / reflux; | 98.6 A mixture of 2-bromopyrimidine (0.43g,2.70mmol), 2-bromopyridine-5-boronic acid (0.55g,2.72mmol), tetrakis(triphenylpnosphine)palladium(0) (3OOmg, 0.259mmol), cesium carbonate (1.15g, 3.03mmol) was stirred in MeOH/toluene/water (15ml, 1/1/1) at reflux temperature overnight. The reaction was cooled to room temperature and diluted with EtOAc (200ml) and water (50ml). The organic layer was separated, dried over MgSd, filtered and solvent evaporated yielding a residue which was purified on silica gel eluting with 25% v/vEtOAc/hexanes yielding product 76 as white solid. (0.55g, 85%) ESMS (MH, 236). |
| 85% | With caesium carbonate In methanol; water; toluene Heating / reflux; | |
| 5% | With caesium carbonate In methanol; water; toluene Heating / reflux; | 16 A mixture of 2-bromopyridine (0.43g,2.70mmol), 2-bromopyridine-5-boronic acid (0.55g,2.72mmol), tetrakis(triphenylphosphine)palladium(0) (3OOmg, 0.259mmol), cesium carbonate (1.15g, 3.03mmol) was stirred in MeOH/toluene/water (15ml, 1/1/1) at reflux temperature overnight. The reaction was cooled to room temperature and diluted with EtOAc (200ml) and water (50ml). The organic layer was separated, dried over MgSO4,filtered and solvent evaporated yielding a residue which was purified on silica gel eluting with 25% v/vEtOAc/hexanes yielding product 76 as white solid. (0.55g, 5%) ESMS (MH, 236). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With sodium carbonate; N,N-dimethyl-formamide at 60℃; for 4h; | 2-bromo-5-phenylpyridine. Na2CO3 (1.117 mL, 2.234 mmol) followed by Pd(PPh3)4 (51.6 mg, 0.045 mmol) were added to a solution of iodobenzene (0.1 mL, 0.894 mmol) and 2-bromopyridine-5-boronic acid (271 mg, 1.340 mmol) in DMF (4 mL). The reaction was heated at 60° C. for 4 h, cooled and concentrated. The residue was partitioned between EtOAc and water. The organic phase was washed with brine, dried (MgSO4), and concentrated. Chromatography over silica eluting with 4:1 hexanes:EtOAc afforded the title compound as an off-white solid. LC-MS: calculated for C11H8BrN 234.09, observed m/e 236.5 (M+H)+ (Rt 1.72 min). | |
| With sodium carbonate In N,N-dimethyl-formamide at 60℃; for 4h; | 14 Na2CO3 (1.117 mL, 2.234 mmol) followed by Pd(PPh3)4 (51.6 mg, 0.045 mmol) were added to a solution of iodobenzene (0.1 mL, 0.894 mmol) and 2- bromoρyridine-5-boronic acid (271 mg, 1.340 mmol) in DMF (4 mL). The reaction was heated at 60 0C for 4 h, cooled and concentrated. The residue was partitioned between EtOAc and water. The organic phase was washed with brine, dried (MgSO4), and concentrated. Chromatography over silica eluting with 4:1 hexanes:EtOAc afforded the title compound as an off-white solid. LC-MS: calculated for C11H8BrN 234.09, observed m/e 236.5 (M + H)+ (Rt 1.72 min). | |
| With sodium carbonate In N,N-dimethyl-formamide at 60℃; for 4h; | 14 Na2CO3 (1.117 niL, 2.234 mmol) followed by Pd(PPh3)4 (51.6 mg, 0.045 mmol) were added to a solution of iodobenzene (0.1 mL, 0.894 mmol) and 2- bromopyridine-5-boronic acid (271 mg, 1.340 mmol) in DMF (4 mL). The reaction was heated at 60 0C for 4 h, cooled and concentrated. The residue was partitioned between EtOAc and water. The organic phase was washed with brine, dried (MgSO4), and concentrated. Chromatography over silica eluting with 4:1 hexanes:EtOAc afforded the title compound as an off-white solid. LC-MS: calculated for C11H8BrN 234.09, observed m/e 236.5 (M + H)+(Rt 1.72 min). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With magnesium sulfate In diethyl ether at 20℃; for 16h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 63% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; N,N-dimethyl-formamide; at 120℃; for 1h;Inert atmosphere; Microwave irradiation; | Step A: Preparation of 2-bromo-5-(4-(trifluoromethoxy)phenyl)pyridine. [00137] To a microwave vial equipped with a magnetic stir bar were added (6-bromopyridin-3- yl)boronic acid (1.37 g, 6.77 mmol), l-iodo-4-(trifluoromethoxy)benzene (1.5 g, 5.21 mmol) and DMF (11.9 mL), followed by K2C03 (2.52 g, 18.2 mmol) and water (2.98 mL). The reaction mixture was stirred under N2 for 5 min and treated with Pd(PPh )4 (16.05 mg, 0.014 mmol). The reaction vessel was capped, placed in a Biotage Initiator microwave reactor for 1 h at 120 C, with external IR-sensor temperature monitoring from the side of the vessel. The cooled reaction mixture was filtered through a pad of Celite rinsing with EtOAc (100 mL), and the filtrate was washed successively with saturated aqueous NaHC03 (50 mL), water (3 x 50 mL), and brine (50 mL). The organic phase was dried over MgS04, filtered, and concentrated. The residue was purified by column chromatography (Si02, 0-M0 EtOAc in hexanes) to give the title compound (1.07 g, 63%) as an off-white solid: IR (Thin Film) 3036, 1453, 1210, 1167 cm"1; 1H NMR (400 MHz, CDC13) δ 8.57 (dd, J = 2.6, 0.8 Hz, 1H), 7.71 (dd, J= 8.2, 2.6 Hz, 1H), 7.63 - 7.54 (m, 3H), 7.38 - 7.29 (m, 2H); 19F NMR (376 MHz, CDC13) δ -57.83; HRMS-ESI (m/z) [M+H]+ calcd for Ci2H8BrF3NO, 317.9736; found, 317.9735. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With pyridine; oxygen; copper diacetate In dichloromethane at 20℃; for 16h; | 1 Step 1-Ethyl 1-(6-bromo-3-pyridyl)-4-nitro-pyrazole-3-carboxylate To a solution of ethyl 4-nitro-1H-pyrazole-3-carboxylate (5.8 g, 31.3 mmol, CAS55864-87-4), pyridine (9.91 g, 125 mmol) and Cu(OAc)2 (8.54 g, 46.9 mmol) in DCM (120 mL) was added (6-bromo-3-pyridyl)boronic acid (7.59 g, 37.5 mmol, CAS223463-14-7). The mixture was stirred at rt for 16 hours under an oxygen atmosphere (15 psi pressure). On completion, the reaction mixture was quenched by adding saturated NH3.H2O solution (40 mL). The organic layer was separated and dried over Na2SO4, filtered and concentrated in vacuo to give a residue. The residue was purified by silica gel chromatography (PE/EA=3/1) to give the title compound (2.30 g, 21% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 9.83 (s, 1H), 9.00 (d, J=2.8 Hz, 1H), 8.31 (dd, J=3.2, 8.8 Hz, 1H), 7.91 (d, J=8.8 Hz, 1H), 4.42 (q, J=7.2 Hz, 2H), 1.33 (t, J=7.2 Hz, 3H). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 72.9% | With copper diacetate; potassium carbonate; triethylamine In chloroform at 20℃; for 13h; | 10 Preparation of intermediate compound [340-1] In a 1L reaction flask under air, the intermediate compound [76-2] 10g (47.57mmol), triethylamine 19.89mL (142.7mmol), copper (II) acetate 25.92g (142.7mmol),6-bromo-3-pyridinylboronic acid 48g (237.83mmol) was slowly added to 300 mL of chloroform at room temperature and stirred for 12 hours. After completion of the reaction, 75 mL of saturated potassium carbonate was added, stirred at room temperature for 1 hour, filtered through Celite, extracted with dichloromethane and distilled water, treated with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, separated and purified by silica gel chromatography using dichloromethane and hexane, and recrystallized from dichloromethane and hexane to prepare 12.7 g (72.9%) of a white solid intermediate compound [340-1]. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 61.1% | With copper (I) iodide; tetrakis-(triphenylphosphine)-palladium; triethylamine In acetonitrile at 20℃; for 6h; Inert atmosphere; | 56.1 Step 1: Synthesis of (6-(4-(piperidin-1-yl)but-1-yn-1-yl)pyridin-3-yl)boronic acid Into a 50 mL reaction flask were sequentially added acetonitrile (20 mL), 1-(but-3-yn-1-yl)piperidine (1.37 g, 10.0 mmol), and 2-bromopyridine-5-boronic acid (2.01 g, 10.0 mmol) , tetrakis(triphenylphosphine)palladium (0.40g, 0.35mmol), cuprous iodide (0.07g, 0.35mmol) and triethylamine (2mL), react at room temperature for 6h under nitrogen protection. TLC monitored the completion of the reaction, the reaction solution was concentrated to dryness, and the residue was subjected to column chromatography (DCM:MeOH=30:1) to obtain (6-(4-(piperidin-1-yl)but-1-yn-1-yl)Pyridin-3-yl)boronic acid (1.26 g, 61.1% yield). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 50.1 % | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 105℃; Inert atmosphere; | 18.18a Step 18a:Preparation of 2-bromo-5-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)pyridine (compound 0103-21): Under nitrogen protection, (6-bromopyridin-3-yl)boronic acid (0101-21) (500 mg, 2.47 mmol, 1.1 equivalent), 4-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole (0102-1) (625 mg, 2.25 mmol, 1.0 equiv),[1,1'-Bis(diphenylphosphine)ferrocene]palladium dichloride (82.4 mg, 0.113 mmol, 0.05 equiv),A mixture of potassium carbonate (931 mg, 6.75 mmol, 3.0 equiv) in dioxane/water (20 mL/2 mL) was stirred at 105°C for 3.0 h.The reaction solution was diluted with water and extracted with ethyl acetate.The organic layer was dried and concentrated under reduced pressure. The residue was purified using a silica gel column (petroleum ether/ethyl acetate = 10/1 to 3/1) to obtain a yellow solid product.2-Bromo-5-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)pyridine (346 mg, yield: 50.1%). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 20 - 100℃; for 16h; Inert atmosphere; | 20A Synthesis of 4-(6-bromopyridin-3-yl)-3-fluorobenzonitrile To a solution of (6-brom opyri din-3 -yl)boronic acid (la) (408.52 mg, 2.02 mmol, 1.0 eq in dioxane (5 mLyiLO (1 mL) was added 3-fluoro-4-iodobenzonitrile (1) (0.5 g, 2.02 mmol, 1.0 eq), K2CO3 (559.52 mg, 4.05 mmol, 2.0 eq), and Pd(dppf)C12 (148.11 mg, 202.42 pmol, 0.1 eq at 20 °C under N2. The mixture was stirred at 100 °C for 16 h under N2. After cooling to 20 °C, the mixture was filtered, and concentrated under reduced pressure to give a residue that was purified by column chromatography (SiCh, petroleum ether/ethyl acetate = 20/1 to 0/1). 4-(6-brom opyri din-3 -yl)-3 -fluorobenzonitrile (2) (200 mg, crude) was obtained and used as is in the next step. 'H NMR: (400 MHz, CDCL): b = 8.48 (s, 1H), 7.68 (td, J= 1.9, 8.3 Hz, 1H), 7.56 (s, 1H), 7.50 (br d, J= 7.5 Hz, 2H), 7.47 - 7.45 (m, 1H). | |
| With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 100℃; for 16h; Inert atmosphere; | Scheme 20A To a solution of (6-bromopyridin-3-yl)boronic acid (1a) (408.52 mg, 2.02 mmol, 1.0 eq) in dioxane (5 mL)/H2O (1 mL) was added 3-fluoro-4-iodobenzonitrile (1) (0.5 g, 2.02 mmol, 1.0 eq), K2CO3 (559.52 mg, 4.05 mmol, 2.0 eq), and Pd(dppf)Cl2 (148.11 mg, 202.42 μmol, 0.1 eq) at 20oC under N2. The mixture was stirred at 100oC for 16 h under N2. After cooling to 20oC, the mixture was filtered, and concentrated under reduced pressure to give a residue that was purified by column chromatography (SiO2, petroleum ether/ethyl acetate = 20/1 to 0/1). 4-(6-bromopyridin-3-yl)-3-fluorobenzonitrile (2) (200 mg, crude) was obtained and used as is in the next step.1H NMR: (400 MHz, CDCl3): δ = 8.48 (s, 1H), 7.68 (td, J = 1.9, 8.3 Hz, 1H), 7.56 (s, 1H), 7.50 (br d, J = 7.5 Hz, 2H), 7.47 - 7.45 (m, 1H) |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 600 mg | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 20 - 100℃; for 12h; | A4-B Synthesis of methyl 2-(6-bromopyridin-3-yl)pyrimidine-5-carboxylate To a solution of methyl 2-bromopyrimidine-5-carboxylate (2) (1.60 g, 7.36 mmol, 1 eq) in dioxane (16 mL) and H2O (1.60 mL) was added K2CO3 (2.03 g, 14.7 mmol, 2 eq) and (6-brom opyri din-3 -yl)boronic acid (3) (1.63 g, 8.09 mmol, 1.10 eq) at 20°C followed by Pd(dppf)C12 (538 mg, 735 umol, 0.10 eq). The mixture was heated to 100°C and stirred for12 hrs. The reaction mixture was filtered, and the filtrate concentrated under reduced pressure to give a residue that was purified by prep-HPLC (column: Phenomenex luna Cl 8 (250 * 70 mm, 15 um); mobile phase: [water (HC1) -ACN]; B%: 35% - 65%, 18 mins) to provide methyl 2-(6-bromopyridin-3-yl)pyrimidine-5-carboxylate (4) (600 mg, 2.04 mmol). TH NMR (400 MHz, chloroform-d) 8 = 9.49 (d, J= 2.4 Hz, 1H), 9.36 (s, 2H), 8.65 (dd, J= 2.4, 8.4 Hz, 1H), 7.67 (d, J= 8.3 Hz, 1H), 4.04 (s, 3H). |
| 600 mg | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 100℃; for 12h; | Scheme A4-B To a solution of methyl 2-bromopyrimidine-5-carboxylate (2) (1.60 g, 7.36 mmol, 1 eq) in dioxane (16 mL) and H2O (1.60 mL) was added K2CO3(2.03 g, 14.7 mmol, 2 eq) and (6-bromopyridin-3-yl)boronic acid (3) (1.63 g, 8.09 mmol, 1.10 eq) at 20°C followed by Pd(dppf)Cl2 (538 mg, 735 µmol, 0.10 eq). The mixture was heated to 100°C and stirred for 12 hrs. The reaction mixture was filtered, and the filtrate concentrated under reduced pressure to give a residue that was purified by prep-HPLC (column: Phenomenex luna C18 (250 * 70 mm, 15 µm); mobile phase: [water (HCl) -ACN]; B%: 35% - 65%, 18 mins) to provide methyl 2-(6-bromopyridin-3-yl)pyrimidine-5-carboxylate (4) (600 mg, 2.04 mmol).1H NMR (400 MHz, chloroform-d) δ = 9.49 (d, J = 2.4 Hz, 1H), 9.36 (s, 2H), 8.65 (dd, J = 2.4, 8.4 Hz, 1H), 7.67 (d, J = 8.3 Hz, 1H), 4.04 (s, 3H). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 20 - 100℃; for 16h; Inert atmosphere; | A5-A Synthesis of 4-(6-bromopyridin-3-yl)-2-fluorobenzonitrile To a solution of 2-fluoro-4-iodobenzonitrile (1) (0.5 g, 2.02 mmol, 1.0 eq) in dioxane (5 mL)/H2O (1 mL) was added (6-brom opyri din-3 -yl)boronic acid (la) (408.52 mg, 2.02 mmol, 1.0 eq), K2CO3 (559.52 mg, 4.05 mmol, 2.0 eq), and Pd(dppf)C12 (148.11 mg, 202.42 pmol, 0.1 eq) at 20°C under N2. The mixture was stirred at 100°C for 16 h under N2. TLC (petroleum ether/ethyl acetate = 5/1, Rf (cpd. 1) = 0.77) indicated that (1) was consumed, and one new spot with larger polarity was detected. After cooling to 20°C, the mixture was filtered, and then the filtrate was concentrated under reduced pressure to give a residue.4-(6-bromopyridin-3-yl)-2-fluorobenzonitrile (2) (650 mg, crude) was obtained.TH NMR: (400 MHz, CDCI3): d = 8.53 (d, J= 2.4 Hz, 1H), 7.71 - 7.65 (m, 2H), 7.56 (d, J= 8.3 Hz, 1H), 7.41 - 7.33 (m, 2H). | |
| With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 100℃; for 16h; Inert atmosphere; | Scheme A5-A To a solution of 2-fluoro-4-iodobenzonitrile (1) (0.5 g, 2.02 mmol, 1.0 eq) in dioxane (5 mL)/H2O (1 mL) was added (6-bromopyridin-3-yl)boronic acid (1a) (408.52 mg, 2.02 mmol, 1.0 eq), K2CO3 (559.52 mg, 4.05 mmol, 2.0 eq), and Pd(dppf)Cl2 (148.11 mg, 202.42 µmol, 0.1 eq) at 20°C under N2. The mixture was stirred at 100°C for 16 h under N2. TLC (petroleum ether/ethyl acetate = 5/1, Rf(cpd.1) = 0.77) indicated that (1) was consumed, and one new spot with larger polarity was detected. After cooling to 20°C, the mixture was filtered, and then the filtrate was concentrated under reduced pressure to give a residue. 4-(6-bromopyridin-3-yl)-2-fluorobenzonitrile (2) (650 mg, crude) was obtained.1H NMR: (400 MHz, CDCl3): δ = 8.53 (d, J = 2.4 Hz, 1H), 7.71 - 7.65 (m, 2H), 7.56 (d, J = 8.3 Hz, 1H), 7.41 - 7.33 (m, 2H). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 80 mg | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 20 - 100℃; for 16h; Inert atmosphere; | A6-B Synthesis of 4-(6-bromopyridin-3-yl)-2,5-difluorobenzonitrile To a solution of 2,5-difluoro-4-iodobenzonitrile (2) (400 mg, 1.51 mmol, 1.00 eq) and (6-brom opyri din-3 -yl)boronic acid (2a) (457 mg, 2.26 mmol, 1.50 eq) in dioxane (4.00 mL) and H2O (0.80 mL) was added K2CO3 (417 mg, 3.02 mmol, 2.00 eq) at 20°C. The suspension was degassed and purged with N2 for 3 times. To the mixture was added Pd(dppf)C12 (HO mg, 151 umol, 0.10 eq) at 20°C under N2. The suspension was degassed and purged with N2 for 3 times. The mixture was stirred at 100°C for 16 hrs under N2. LCMS showed that (2) was consumed completely and one main peak with desired mass was detected. The reaction mixture was diluted with H2O 5.00 mL and extracted with EtOAc 30.0 mL (15.0 mL * 3). The combined organic layers were dried over ISfeSCU, filtered and concentrated under reduced pressure to give a residue. The residue was purified by prep-TLC (SiCh, Petroleum ether/ Ethyl acetate = 2/ 1). 4-(6-bromopyridin-3-yl)-2,5-difluorobenzonitrile (3) (80.0 mg, 244.00 umol) was obtained. |
| 80 mg | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 100℃; for 16h; Inert atmosphere; | Scheme A6-B To a solution of 2,5-difluoro-4-iodobenzonitrile (2) (400 mg, 1.51 mmol, 1.00 eq) and (6-bromopyridin-3-yl)boronic acid (2a) (457 mg, 2.26 mmol, 1.50 eq) in dioxane (4.00 mL) and H2O (0.80 mL) was added K2CO3 (417 mg, 3.02 mmol, 2.00 eq) at 20°C. The suspension was degassed and purged with N2 for 3 times. To the mixture was added Pd(dppf)Cl2(110 mg, 151 µmol, 0.10 eq) at 20°C under N2. The suspension was degassed and purged with N2 for 3 times. The mixture was stirred at 100°C for 16 hrs under N2. LCMS showed that (2) was consumed completely and one main peak with desired mass was detected. The reaction mixture was diluted with H2O 5.00 mL and extracted with EtOAc 30.0 mL (15.0 mL * 3). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue. The residue was purified by prep-TLC (SiO2, Petroleum ether/ Ethyl acetate = 2/ 1). 4-(6-bromopyridin-3-yl)-2,5-difluorobenzonitrile (3) (80.0 mg, 244.00 µmol) was obtained. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 2.72 g | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 90℃; for 24h; Alkaline conditions; Inert atmosphere; | 3 2-Bromo-5-iodo-4-pyridinamine (10.07 mmol, 3.00 g) and 6-bromopyridin-3-boronic acid (12.08 mmol, 2.43 g) were dissolved in toluene (27 mL), ethanol (9 mL), and a 2 mol/L KCO aqueous solution (18 mL) to provide an alkaline environment. After freezing, the mixture was refluxed under vacuum for 5 min. 180.00 mg (0.16 mmol, 0.05 eq) of tetrakis(triphenylphosphine)palladium was added, and the mixture was subjected to a freeze-thaw cycle under vacuum twice. The mixture was stirred and refluxed at 90 °C for 24 h under a nitrogen atmosphere. After cooling to room temperature, the reaction mixture was diluted with water. It was then extracted with dichloromethane and dried over anhydrous NaSO to obtain the organic extract. The solvent was evaporated under reduced pressure, and the residue was dissolved in a small amount of dichloromethane. The residue was separated by column chromatography on silica gel at a petroleum ether:dichloromethane ratio of 2:1. The second elution product yielded 2.72 g of DN55. |
Tags: BPBA | 2-Bromopyridine-5-boronic acid | Pyridines | Bromides | Organoboron | Boronic Acids | Organometallic Reagents | Organic Building Blocks | Heterocyclic Building Blocks | Boronic Acids/Esters | 223463-14-7
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| H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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