Dichloromethane → 2-Chloro-4-(4-chlorophenyl)-3,4'-bipyridine

HRID 2101315ノート

反応式

HRID 2101315 の反応式
Br[C:2]1[C:3]([Cl:15])=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1.CC1(C)C(C)(C)OB([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)O1.ClCCl.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1COCC1.CCOC(C)=O.O>[Cl:15][C:3]1[C:2]([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)=[C:7]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[CH:6]=[CH:5][N:4]=1

参加物

8

反応物 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 27346484-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 577993673-Bromo-2-chloro-4-(4-chlorophenyl)pyridine

生成物 1

HCID 577993632-Chloro-4-(4-chlorophenyl)-3,4'-bipyridine収率 62.9%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

In a pressure tube, to a stirring solution of 3-bromo-2-chloro-4-(4-chlorophenyl)pyridine (1.3 g, 4.49 mmol) in THF (60 mL) at room temperature under argon was added 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (2.3 g, 11.21 mmol), 1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride complex with dichloromethane (350 mg, 0.43 mmol), and powdered K3PO4 (1.9 g, 8.96 mmol). The resulting suspension was stirred and heated at 100° C. under argon for 12 h. After the reaction mixture was cooled to room temperature, water (40 mL) and EtOAc (50 mL) were added. The layers were separated. The organic layer was dried (MgSO4), filtered, and concentrated under reduced pressure. The crude product was purified by flash chromatography (silica gel column eluting with 20% ethyl acetate-hexanes) to isolate 850 mg of the title compound as a white solid. HPLC/MS: retention time=2.157 min, [M+H]+=301.

後処理

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. customThe layers were separated
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by flash chromatography (silica gel column eluting with 20% ethyl acetate-hexanes)

出典と根拠

ORDレコード
ord-691bb2c0b93c4b33a3e01d8eef584046
出典データセット
uspto-grants-2009_08
特許番号
US07572808B2

反応ノート

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