Triphenylphosphine → 5'-Bromo-2,3'-bipyridine

HRID 50571ノート

反応式

HRID 50571 の反応式
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[N:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[Zn+]>C1COCC1.CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Br:8][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][N:29]=2)[CH:7]=1

参加物

7

反応物 3

HCID 11776TriphenylphosphineHCID 693693,5-DibromopyridineHCID 178479831HCID 178479831、化合物

生成物 1

HCID 227351815'-Bromo-2,3'-bipyridine

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 3,5-dibromopyridine (2.5 g, 10.5 mmol), PPh3 (210 mg, 0.8 mmol) in degassed THF (2 mL) was treated with Pd2(dba)3 (Tris(dibenzylideneacetone)dipalladium (0), 91.5 mg, 0.1 mmol) at 25° C. under N2. A solution of 2-pyridinyl zinc chloride (21 mL, 0.5 M in THF, Aldrich) in THF was added and the resulting solution was warmed to reflux for 16 h. The solution was allowed to cool to room temperature, diluted with EtOAc (200 mL), washed with water (2×100 mL), dried (MgSO4), filtered and was concentrated in vacuo. Purification by flash chromatography (EtOAc) afforded the title compound as a white solid. MS 236 (M+H)+.

後処理

  1. temperaturethe resulting solution was warmed
  2. temperatureto reflux for 16 h
  3. washwashed with water (2×100 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationwas concentrated in vacuo
  7. customPurification by flash chromatography (EtOAc)

出典と根拠

ORDレコード
ord-a28cba4d344a4cdb91c299195a232b19
出典データセット
uspto-grants-2004_03
特許番号
US06713455B2

反応ノート

読み込み中…