HCID 90203845、化合物 → HCID 90203632、化合物

HRID 1480216ノート

反応式

HRID 1480216 の反応式
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([CH:9]2[CH2:11][CH2:10]2)=[CH:4][N:3]=1.[C:12]([Zn]C#N)#[N:13]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].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]>[Cl:8][C:6]1[C:5]([CH:9]2[CH2:11][CH2:10]2)=[CH:4][N:3]=[C:2]([C:12]#[N:13])[CH:7]=1

参加物

6

反応物 2

HCID 90203845HCID 90203845、化合物HCID 178514179HCID 178514179、化合物

生成物 1

HCID 90203632HCID 90203632、化合物収率 73.2%

試薬・触媒・溶媒 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a stirred solution of 2,4-dichloro-5-cyclopropyl-pyridine (example 145a, 2.2 g, 11.76 mmol) in DMF (10 ml) and purged the reaction mixture argon for 10 minutes. To this reaction was added dicyanozinc (926 mg, 7.65 mmol) followed by DPPF (520 mg, 1.02 mmol) and Pd2dba3 (535 mg, 0.58 mmol) at 25° C. and the reaction mixture was again purged with argon for 10 min. The reaction mixture was heated up to 100° C. for 1 hour. The catalyst was filtered off and the solution was diluted with ethyl acetate. The organic phase was poured into a separatory funnel and extracted with brine. The organic phase was dried over sodium sulfate and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica eluting with a heptane/ethyl acetate gradient to yield the title compound (1 g, 50%). MS (ESI, m/z): 179.2 (M+H+).

後処理

  1. customthe reaction mixture was again purged with argon for 10 min
  2. filtrationThe catalyst was filtered off
  3. additionthe solution was diluted with ethyl acetate
  4. additionThe organic phase was poured into a separatory funnel
  5. extractionextracted with brine
  6. dry with materialThe organic phase was dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material was purified by flash chromatography on silica eluting with a heptane/ethyl acetate gradient

出典と根拠

ORDレコード
ord-6254611aed0c49ffb3278978323708ac
出典データセット
uspto-grants-2016_08
特許番号
US09409866B2

反応ノート

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