HCID 90203845、化合物 → HCID 90203632、化合物

HRID 1480282ノート

反応式

HRID 1480282 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

A stirred solution of 2,4-dichloro-5-cyclopropylpyridine (example 215a, 2.2 g, 11.76 mmol) in DMF (10 ml) was purged with argon for 10 minutes. To this reaction mixture was added dicyanozinc (926 mg, 7.65 mmol) followed by addition of DPPF (520 mg, 1.02 mmol) and Pd2dba3 (535 mg, 0.58 mmol). The reaction mixture was again purged with argon for 10 minutes. The reaction mixture was then stirred at 100° C. for 1 hour. The catalyst was filtered off on a pad of celite and the filtrate was diluted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate and evaporated down to dryness. The obtained crude material was purified by flash chromatography on silica eluting with a gradient of heptane and ethyl acetate to yield the title compound (1 g, 50%) as off white crystalline solid. MS (ESI, m/z): 179.2 (M+H+).

後処理

  1. customThe reaction mixture was again purged with argon for 10 minutes
  2. filtrationThe catalyst was filtered off on a pad of celite
  3. additionthe filtrate was diluted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated down to dryness
  7. customThe obtained crude material
  8. customwas purified by flash chromatography on silica eluting with a gradient of heptane and ethyl acetate

出典と根拠

ORDレコード
ord-1ec5f9ad26c74cf8a36aa084f8d37536
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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