2,6-Dibromopyridine → HCID 19966486, 화합물

HRID 977600

반응식

HRID 977600 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[CH3:9][O:10][C:11](=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[CH:19])[CH:13]=1>C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Br:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:19]#[C:18][C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([C:11]([O:10][CH3:9])=[O:20])[CH:13]=2)[N:3]=1

참가 물질

6

반응물 2

HCID 122742,6-DibromopyridineHCID 112751593-Ethynylbenzoic acid methyl ester

생성물 1

HCID 19966486HCID 19966486, 화합물수율 23.8%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8471Triethylamine용매

실험 절차

A solution of 15.1 g of 2,6-dibromopyridine in 500 ml of triethylamine is mixed under ice cooling with 10.2 g of 3-ethinylbenzoic acid methyl ester, 1.1 g of bis-(triphenylphosphine)-palladium(II) chloride and 150 mg of copper(I) iodide and the mixture is stirred for 1 hour. Then, the ice bath is removed and it is stirred for 48 hours at room temperature. The precipitate is filtered off, the filtrate is evaporated to dryness, mixed with water and shaken out with ethyl acetate. The organic phase is dried on sodium sulfate, concentrated by evaporation and the residue is chromatographed on silica gel with hexane/0-12% ethyl acetate. 4.8 g of 2-bromo-6-[2-(3-methoxycarbonyiphenyl)-ethinyl]-pyridine of melting point 12°-126° C. is obtained.

후처리

  1. customThen, the ice bath is removed
  2. stirringit is stirred for 48 hours at room temperature
  3. filtrationThe precipitate is filtered off
  4. customthe filtrate is evaporated to dryness
  5. additionmixed with water
  6. stirringshaken out with ethyl acetate
  7. customThe organic phase is dried on sodium sulfate
  8. concentrationconcentrated by evaporation
  9. customthe residue is chromatographed on silica gel with hexane/0-12% ethyl acetate

출처 및 근거

ORD 기록
ord-4bb28497933843ff97b13aab94eb29fe
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05614634

연결된 노트

불러오는 중…