6-Bromoquinoline → (Quinolin-6-yl)acetonitrile

HRID 1099056

반응식

HRID 1099056 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.C[Si]([CH2:16][C:17]#[N:18])(C)C>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].[F-].[F-].[Zn+2].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>[N:8]1[C:9]2[C:4](=[CH:3][C:2]([CH2:16][C:17]#[N:18])=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 2

HCID 792436-BromoquinolineHCID 87557(Trimethylsilyl)acetonitrile

생성물 1

HCID 21992552(Quinolin-6-yl)acetonitrile수율 72.1%

시약·촉매·용매 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 10129912Zinc(II) fluoride촉매HCID 6228Dimethylformamide용매

실험 절차

To a mixture of (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (6.7 g, 0.012 mol), tris(dibenzylideneacetone)dipalladium(0) (10.0 g, 0.012 mol), 6-bromoquinoline (120.0 g, 0.577 mol) in DMF (360 mL) in a 3-neck round bottom flask with stirring under an atmosphere of nitrogen was added (trimethylsilyl)acetonitrile (98.7 mL, 0.721 mol), followed by zinc difluoride (42 g, 0.40 mol). The flask was sealed under an atmosphere of nitrogen. The reaction was stirred at 105° C. for 20 h. After cooling the solution to RT, the reaction mixture was quenched with aqueous ammonia solution and extracted with ethyl acetate (3×500 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was chromatographed on a silica gel column (ethyl acetate in hexanes: 0-65%) to afford the desired product quinolin-6-ylacetonitrile (70 g, 72.1%). Analytical LCMS: (M+H)+=168.9.

후처리

  1. customThe flask was sealed under an atmosphere of nitrogen
  2. stirringThe reaction was stirred at 105° C. for 20 h
  3. customthe reaction mixture was quenched with aqueous ammonia solution
  4. extractionextracted with ethyl acetate (3×500 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was chromatographed on a silica gel column (ethyl acetate in hexanes: 0-65%)

출처 및 근거

ORD 기록
ord-51ed9ee3cb0c4abb86c3caec7c5a6dad
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143251B2

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