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

HRID 50571노트

반응식

HRID 50571 반응식
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

참가 물질

7

반응물 3

HCID 11776TriphenylphosphineHCID 693693,5-DibromopyridineHCID 178479831HCID 178479831, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-a28cba4d344a4cdb91c299195a232b19
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713455B2

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