HCID 90203845, 화합물 → HCID 90203632, 화합물

HRID 1480282노트

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HRID 1480282 반응식
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

참가 물질

6

반응물 2

HCID 90203845HCID 90203845, 화합물HCID 178514179HCID 178514179, 화합물

생성물 1

HCID 90203632HCID 90203632, 화합물수율 73.2%

시약·촉매·용매 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-1ec5f9ad26c74cf8a36aa084f8d37536
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409866B2

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