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

HRID 589095

반응식

HRID 589095 반응식
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

참가 물질

5

반응물 2

HCID 6077842-(Tributylstannyl)pyridineHCID 27627562-Bromoquinoline

생성물 1

HCID 6099112-(2-Pyridinyl)quinoline수율 78%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
110 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2f1faf5af9ca4d319a3f2a42a272de81
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227985B2

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