Dimethylacetamide → 3-cyano-2-(4-fluoro-phenyl)-4-hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

HRID 642433ノート

反応式

HRID 642433 の反応式
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:29])=[C:8]2[C:14](Br)=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[N:12]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2].C[C:31]([N:33](C)C)=O>[C-]#N.[C-]#N.[Zn+2].[Zn].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]>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:29])=[C:8]2[C:14]([C:31]#[N:33])=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[N:12]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2]

参加物

7

反応物 2

HCID 31374DimethylacetamideHCID 684284133-bromo-2-(4-fluoro-phenyl)-4-hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

生成物 1

HCID 684264153-cyano-2-(4-fluoro-phenyl)-4-hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

試薬・触媒・溶媒 4

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 23994Zinc触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒

反応条件

温度
120 °C

実験手順

A mixture of 3-bromo-2-(4-fluoro-phenyl)-4-hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (200 mg), Zn(CN)2 (31 mg), Zn dust (3.5 mg), Pd2(dba)3 (20 mg), dppf (24.4 mg) in DMA (1 mL) was heated to 120° C. for 145 min; then the mixture was partitioned between EtOAc and water, the organic phase was then washed with sat. NaCl solution, dried over anhydrous sodium sulfate, filtered and concentrated sequentially to give a residue, which was purified with column to give desired title compound (83 mg). The title compound, ESI MS (m/z): 402 (M+H)+.

後処理

  1. customthen the mixture was partitioned between EtOAc and water
  2. washthe organic phase was then washed with sat. NaCl solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated sequentially
  6. customto give a residue, which
  7. customwas purified with column

出典と根拠

ORDレコード
ord-726ef012e1764e278782f056c62d5084
出典データセット
uspto-grants-2010_04
特許番号
US07696223B2

反応ノート

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