2-(Tributylstannyl)pyridine → 2-(2-Pyridinyl)quinoline

HRID 589095

反応式

HRID 589095 の反応式
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C([Sn](CCCC)(CCCC)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1)CCC>CN(C)C=O.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>[N:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

参加物

5

反応物 2

HCID 6077842-(Tributylstannyl)pyridineHCID 27627562-Bromoquinoline

生成物 1

HCID 6099112-(2-Pyridinyl)quinoline収率 78%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

A solution of 2-bromoquinoline (1.00 g, 4.81 mmol) [Aldrich, cat. #716278] in N,N-dimethylformamide (10.0 mL) (degassed with nitrogen) was treated with 2-(tributylstannyl)pyridine (1.83 mL, 4.81 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.337 g, 0.481 mmol). The reaction mixture was degassed with nitrogen for 5 min and heated at 110° C. for 17 h. The reaction mixture was then diluted with water (50 mL) and ether (50 mL) and filtered over Celite. The solids were washed with additional ether (150 mL). The filtrate was washed with water (150 mL) and brine, dried over sodium sulfate, filtered, and concentrated to give a crude residue. Purification by flash column chromatography (100% hexanes to 70% ethyl acetate/hexanes, the ethyl acetate containing 5% methanol) gave the desired product (0.771 g, 78%). LCMS calculated for C14H11N2 (M+H)+: m/z=207.1. found: 207.1.

後処理

  1. customThe reaction mixture was degassed with nitrogen for 5 min
  2. additionThe reaction mixture was then diluted with water (50 mL) and ether (50 mL)
  3. filtrationfiltered over Celite
  4. washThe solids were washed with additional ether (150 mL)
  5. washThe filtrate was washed with water (150 mL) and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a crude residue
  10. customPurification by flash column chromatography (100% hexanes to 70% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-2f1faf5af9ca4d319a3f2a42a272de81
出典データセット
uspto-grants-2016_01
特許番号
US09227985B2

関連ノート

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