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

HRID 1099056

反応式

HRID 1099056 の反応式
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

参加物

7

反応物 2

HCID 792436-BromoquinolineHCID 87557(Trimethylsilyl)acetonitrile

生成物 1

HCID 21992552(Quinolin-6-yl)acetonitrile収率 72.1%

試薬・触媒・溶媒 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 10129912Zinc(II) fluoride触媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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%)

出典と根拠

ORDレコード
ord-51ed9ee3cb0c4abb86c3caec7c5a6dad
出典データセット
uspto-grants-2012_03
特許番号
US08143251B2

関連ノート

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