Dimethylformamide → HCID 86711680, 화합물

HRID 710656노트

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HRID 710656 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[CH2:15][CH2:14][CH2:13][N:12]([C:17](=[O:25])[CH2:18][N:19]4[CH:23]=[C:22](I)[CH:21]=[N:20]4)[C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[CH3:26][N:27](C=O)C>[C-]#N.[C-]#N.[Zn+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].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]>[C:26]([C:22]1[CH:21]=[N:20][N:19]([CH2:18][C:17]([N:12]2[CH2:13][CH2:14][CH2:15][C:16]3[N:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)[N:9]=[CH:10][C:11]2=3)=[O:25])[CH:23]=1)#[N:27]

참가 물질

6

반응물 2

HCID 6228DimethylformamideHCID 86711679HCID 86711679, 화합물

생성물 1

HCID 86711680HCID 86711680, 화합물수율 68%

시약·촉매·용매 3

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매

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온도
90 °C

실험 절차

A mixture of 1-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]-2-(4-iodopyrazol-1-yl)ethanone (0.388 g, 0.86 mmol), Zn(CN)2 (0.151 g, 1.29 mmol), Pd2(dba)3 (0.079 g, 0.086 mmol) and dppf (0.072 g, 0.13 mmol) in DMF (10 mL) was heated at 90° C. for 1 hr. It was then cooled to rt. The mixture was partitioned between EtOAc (10 mL) and sat. NaHCO3 (50 mL). The organic layer was separated, dried over Na2SO4, concentrated in vacuo, and purified by flash chromatography with a gradient elution of 0-100% EtOAc/CH2Cl2 to afford 2-(4-cyanopyrazol-1-yl)-1-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]ethanone (0.205 g, 68%).

후처리

  1. temperatureIt was then cooled to rt
  2. customThe mixture was partitioned between EtOAc (10 mL) and sat. NaHCO3 (50 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography with a gradient elution of 0-100% EtOAc/CH2Cl2

출처 및 근거

ORD 기록
ord-1664379e196741fab855f6d259641fba
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181241B2

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