Dimethylformamide → HCID 86711680、化合物

HRID 710656ノート

反応式

HRID 710656 の反応式
[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]

参加物

6

反応物 2

HCID 6228DimethylformamideHCID 86711679HCID 86711679、化合物

生成物 1

HCID 86711680HCID 86711680、化合物収率 68%

試薬・触媒・溶媒 3

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

反応条件

温度
90 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-1664379e196741fab855f6d259641fba
出典データセット
uspto-grants-2015_11
特許番号
US09181241B2

反応ノート

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