Dichloromethane → 5,5-dimethyl-6-oxo-6-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-hexanenitrile

HRID 1677522ノート

反応式

HRID 1677522 の反応式
Br[C:2]1[N:3]=[C:4]2[C:10]([C:11](=[O:20])[C:12]([CH3:19])([CH3:18])[CH2:13][CH2:14][CH2:15][C:16]#[N:17])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH3:21][O:22][C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[C:27]([O:31][CH3:32])[C:28]=1[O:29][CH3:30].C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>O1CCOCC1.O.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.Cl[Pd]Cl.[Fe+2]>[CH3:18][C:12]([CH3:19])([C:11](=[O:20])[C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([C:25]3[CH:26]=[C:27]([O:31][CH3:32])[C:28]([O:29][CH3:30])=[C:23]([O:22][CH3:21])[CH:24]=3)[N:3]=2)[NH:8][CH:9]=1)[CH2:13][CH2:14][CH2:15][C:16]#[N:17]

参加物

8

反応物 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 27343903,4,5-Trimethoxybenzeneboronic acidHCID 595407676-(2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-5,5-dimethyl-6-oxo-hexanenitrile

生成物 1

HCID 595407395,5-dimethyl-6-oxo-6-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-hexanenitrile収率 4%

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

A mixture of 6-(2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-5,5-dimethyl-6-oxo-hexanenitrile (0.079 g, 0.236 mmol), 3,4,5-trimethoxyphenylboronic acid (0.055 g, 0.26 mmol), potassium carbonate (0.098 g, 0.71 mmol) and Pd(dppf)Cl2.CH2Cl2 (0.019 g, 0.024 mmol) in 2.4 mL of 1,4-dioxane and 0.4 mL of water was stirred at 120° C. in a microwave for 1 h, then at 130° C. in a microwave for 1 h. The resulting mixture was partitioned between 50 mL of ethyl acetate and 25 mL of water. The organic layer was dried over MgSO4, filtered, and concentrated to a residue. Column chromatography (0→100% EtOAc/hexanes) afforded 0.004 g (4%) of 5,5-dimethyl-6-oxo-6-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-hexanenitrile as a white solid.

後処理

  1. customThe resulting mixture was partitioned between 50 mL of ethyl acetate and 25 mL of water
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to a residue

出典と根拠

ORDレコード
ord-096b93453aab47e6a0cf25c7f77b20a2
出典データセット
uspto-grants-2011_08
特許番号
US08008298B2

反応ノート

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