2,6-Dibromopyridine → HCID 19966486、化合物

HRID 977600

反応式

HRID 977600 の反応式
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

参加物

6

反応物 2

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

生成物 1

HCID 19966486HCID 19966486、化合物収率 23.8%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 8471Triethylamine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4bb28497933843ff97b13aab94eb29fe
出典データセット
uspto-grants-1997_03
特許番号
US05614634

関連ノート

読み込み中…