2,5-Dibromopyridine → 5-Bromo-3'-fluoro-2,4'-bipyridine

HRID 42022

反応式

HRID 42022 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[F:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][C:15]=1[Sn](CCCC)(CCCC)CCCC>CN(C=O)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:5]1[CH:6]=[CH:7][C:2]([C:15]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[F:9])=[N:3][CH:4]=1

参加物

6

反応物 2

HCID 693532,5-DibromopyridineHCID 222736013-Fluoro-4-(tributylstannyl)pyridine

生成物 1

HCID 584158125-Bromo-3'-fluoro-2,4'-bipyridine収率 62%

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 6228Dimethylformamide溶媒

反応条件

温度
130 °C

実験手順

In a schlenck tube, a mixture of 2,5-dibromopyridine (2.11 mmol, 0.500 g), 3-fluoro-4-(tributylstannyl)pyridine (2.32 mmol, 0.896 g), PdCl2(PPh3)2 (0.21 mmol, 0.148 g), CuI (0.43 mmol, 0.080 g) in DMF (5 ml) was heated at 130° C. for 12 hours, under argon atmosphere. The solvent was evaporated and the crude mixture was extracted between water and ethyl acetate. The solid residue was purified by chromatography over SiO2 eluting with DCM/methanol mixtures affording 0.330 g (yield 62%) of the expected product.

後処理

  1. customThe solvent was evaporated
  2. extractionthe crude mixture was extracted between water and ethyl acetate
  3. customThe solid residue was purified by chromatography over SiO2 eluting with DCM/methanol

出典と根拠

ORDレコード
ord-a11cea2e8f2340d298289a02033d0720
出典データセット
uspto-grants-2013_09
特許番号
US08536165B2

関連ノート

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