2-Bromo-6-phenylpyridine

2-Bromo-6-phenylpyridine 2, 6-Dibromopyridine (2 g, 8.44 mmol), phenylboronic acid (1 .03 g, 8.44 mmol), potassium carbonate (4.67 g, 33.77 mmol) and TBAB (271 mg, 0.84 mmol) were combined in a mixture of 1 , 4-dioxane (16 ml) and water (4 ml). The reaction mixture was degassed by bubbling nitrogen through for 30 min prior to the addition of PdCIA mixture of 2, 6-dibromopyridine (2.36 g, 10 mmol), phenylboronic acid (1.0 eq), Pd(OAc)1L round bottom flask equipped with in-flown plugging of the condensing tube, a nitrogen inlet port, one of the and 2, 6-dibromopyridine (15. 3 g, 64. 58 mmol), phenyl boronic acid (7. 87 g, 64. 58 mmol), and potassium carbonate (17. 58 g, 129. 16 mmol) a, 228 ml of water is added and 150 ml dimethoxyethane. The mixed nitrogen bubbling directly 15 minutes. Tetrakisphenol palladium (triphenylphosgene) (0) (1. 85 g, 1. 60 mmol) is added, the reaction mixture is heated to reflux. 3 after the completion of heating the reaction time. It is cooled to room temperature, water and diluted with ethyl acetate. Separating layer, a water layer is extracted with ethyl acetate. The organic layer is dried on magnesium sulfate, filtered, the solvent is evaporated. The substance is, 2percent ethyl acetate/hydroxyhexanamide column chromatography eluted and, subsequently, to collect the product 150 °C kouguell roll is used in a vacuum purified by distillation. 5. The obtained product of 2g (34percent).Pitching 2 L flask, 2, 6-dibromo-pyridine (2, 6-dibromopyridine) 5g (0.0213mol), phenylboronic acid (phenylboronic acid) in1.3g (0.0106mol) and Pd (PPh3) 4 put 0.367g (0.32mmol) for the 36 mL Toluene 700 mL EtOH, and under a nitrogen atmosphereAfter the hash Keene, by the addition of 2M K2CO3 solution 10mL and stirred under reflux. After the reaction was terminated to cool to room temperature and 20mL H2OIt was added. Drying the mixture and then extracted twice with EtOAc 50 mL extract with Na2SO4, filtered and concentrated under a reduced pressure.Purification of the resulting compound by silica gel column chromatography to give 0.38 g compound (Intermediate 8) (yield: 15percent) of a white solid was obtained.To a mixture of 2, 6-dibromopyridine (3.50 g, 14.8 mmol) and phenylboronic acid (1.80 g, 14.8 mmol) in N, N-dimethylformamide (20 mL) at room temperature under nitrogen, a solution of tribasic potassium phosphate (7.80 g, 36.7 mmol) in water (14 mL) and bis(triphenylphoshine)palladium(II) dichloride (518 mg, 0.74 mmol) were added. Butyllithium (50 mL, 118 mmol), hexanes (100 mL) and dimethylaminoethanol (5.91 mL, 59.0 mmol) were combined and cooled to -10°C, 2-Phenylpyridine (7.63 g, 49.2 mmol) was added dropwise over 5 minutes to form a clear orange solution. After 1 h, the solution had darkened to red-orange. The solution was then cooled to -40°C and THF (500 mL) that had been cooled to -35°C was added. Immediately 1, 2-dibromoethane (25.4 mL, 295 mmol) was added in one portion, and the mixture was warmed to ambient temperature. The volatiles were removed by evaporation and the yellow oily paste was dissolved in Et^O (125 mL) and water (100 mL). The aqueous layer was removed and the organics were dried over brine, then sodium sulfate. Evaporation of the ether afforded crude product that was crystallized from hexanes as yellow crystals (8.0 g, 69percent).To N, N-dimethylethanolamine (0.8 mL, 8.00 mmol) in heptane (10 mL) cooled externally to 0° C. was added dropwise a 2.5 M n-butyllithium solution (6.40 mL) and the reaction mixture stirred for 30 minutes. 2-Phenylpyridine (12) (412 mg, 2.66 mmol) in heptane (5 mL) was then added and the reaction mixture stirred for a further 1 hour. The reaction was then cooled and carbon tetrabromide (3.18 g, 9.60 mmol) was added whilst maintaining the temperature at -78° C. The reaction was kept at -78° C. for 1 hour and then allowed to warm to ambient temperature. Water was cautiously added and extracted with TBME (.x.2), dried (NaGeneral procedure: Suzuki–Miyaura couplings were performed in glass tubes suitable for microwave. Halopyridines (0.44 mmol), phenyl boronic acid (65.17 mg, 0.53 mmol), LiButyllithium (50 mL, 118 mmol), hexanes (100 mL) and dimethylaminoethanol (5.91 mL, 59.0 mmol) were combined and cooled to -10C, 2-Phenylpyridine (7.63 g, 49.2 mmol) was added dropwise over 5 minutes to form a clear orange solution. After 1 h, the solution had darkened to red-orange. The solution was then cooled to -40C and THF (500 mL) that had been cooled to -35C was added. Immediately 1, 2-dibromoethane (25.4 mL, 295 mmol) was added in one portion, and the mixture was warmed to ambient temperature. The volatiles were removed by evaporation and the yellow oily paste was dissolved in Et^O (125 mL) and water (100 mL). The aqueous layer was removed and the organics were dried over brine, then sodium sulfate. Evaporation of the ether afforded crude product that was crystallized from hexanes as yellow crystals (8.0 g, 69%).To N, N-dimethylethanolamine (0.8 mL, 8.00 mmol) in heptane (10 mL) cooled externally to 0 C. was added dropwise a 2.5 M n-butyllithium solution (6.40 mL) and the reaction mixture stirred for 30 minutes. 2-Phenylpyridine (12) (412 mg, 2.66 mmol) in heptane (5 mL) was then added and the reaction mixture stirred for a further 1 hour. The reaction was then cooled and carbon tetrabromide (3.18 g, 9.60 mmol) was added whilst maintaining the temperature at -78 C. The reaction was kept at -78 C. for 1 hour and then allowed to warm to ambient temperature. Water was cautiously added and extracted with TBME (×2), dried (Na2SO4) and the solvent concentrated in vacuo. The crude product was purified by column chromatography eluting with 5% EtOAc in heptane to give the title compound. Yield: 300 mg, 48%; LC-MS 41.63 min; HPLC Purity: 97%; MS (ES+) m/z 234, 236 (M+H)The title compound was prepared according to the method described in a document (J. Org. Chem., 2003, 68, 4918-4992). In a nitrogen atmosphere, a mixture of dimethylaminoethanol (2.1 ml) and a hexane solution of 2-phenylpyridine (2.17 g) was cooled to -78C, then a hexane solution of n-butyllithium (1.6 M, 26.5 ml) was added dropwise thereto. After dropwise, the mixture was allowed to warm to 0C , then stirred for 2 hours. Thereafter, a toluene solution of bromine (2.5 ml) was added to the mixture at 0C, then stirred for 2 hours additionally. Then, the mixture was stirred at room temperature for 1 day. Thereafter, the residual bromine of reaction mixture was neutralized by aqueous sodium thiosulfate, the mixture was extracted with toluene, the solvent was distilled off, and the residue was purified by silica gel column chromatography, thereby obtaining desired white solid (1.30 g). 1H-NMR(CDCl3):7.39-7.53, 7.55-7.71(m, 2H), 7.96-8.02(m, 2H)General procedure: 2, 6-dibromopyridine 6.0g (25.3 mmol) was dissolved in 100ml of toluene and then, Tetrakistriphenylphosphine Pd (0) 1.5g (1.3 mmol) was added at the room temperature was stirred for about 5 minutes dongan. Thereafter, it was added 7.4g of intermediate 12-3 (25.3 mmol) and sodium carbonate 8.0g (75.9 mmol). Then, 30ml of distilled water was added was heated at reflux for a day. After the reaction was completed, distilled under reduced pressure and filtered through a diatomaceous earth. The resulting mixture was extracted with ethyl acetate going up to 400ml and 100ml of distilled water, and was distilled under reduced pressure the organic layer was dried over magnesium sulfate. Purification of the separation results obtained therefrom by column chromatography to yield intermediate 12-2 to about 4.6g (14.2 mmol, 56% yield). The resulting compound is LC-It was confirmed by MS.Add

Molecular Weight:234.09
XLogP3:3.5
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:232.98401
Monoisotopic Mass:232.98401
Topological Polar Surface Area:12.9
Heavy Atom Count:13
Complexity:154
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes