Sodium Carbonate → 2-Fluoro-4-[7-(1-quinolin-6-ylethyl)imidazo[1,2-b][1,2,4]triazin-2-yl]benzonitrile

HRID 500242ノート

反応式

HRID 500242 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]3[N:12]([C:14]([CH:17]([C:19]4[CH:20]=[C:21]5[C:26](=[CH:27][CH:28]=4)[N:25]=[CH:24][CH:23]=[CH:22]5)[CH3:18])=[CH:15][N:16]=3)[N:13]=2)=[CH:4][C:3]=1[F:29].C(=O)([O-])[O-].[Na+].[Na+].[CH3:36][N:37](C)C(=O)C>CCOC(C)=O.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.O.O.O.[K+].[K+].[K+].[K+].[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:29][C:3]1[CH:4]=[C:5]([C:8]2[CH:9]=[N:10][C:11]3[N:12]([C:14]([CH:17]([C:19]4[CH:20]=[C:21]5[C:26](=[CH:27][CH:28]=4)[N:25]=[CH:24][CH:23]=[CH:22]5)[CH3:18])=[CH:15][N:16]=3)[N:13]=2)[CH:6]=[CH:7][C:2]=1[C:36]#[N:37]

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 31374DimethylacetamideHCID 672243466-1-[2-(4-Bromo-3-fluorophenyl)imidazo[1,2-b][1,2,4]triazin-7-yl]ethylquinoline

生成物 1

HCID 672248682-Fluoro-4-[7-(1-quinolin-6-ylethyl)imidazo[1,2-b][1,2,4]triazin-2-yl]benzonitrile収率 60%

試薬・触媒・溶媒 3

HCID 161067Potassium ferrocyanide trihydrate触媒HCID 167845palladium(II) acetate触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

A mixture of 6-1-[2-(4-bromo-3-fluorophenyl)imidazo[1,2-b][1,2,4]triazin-7-yl]ethylquinoline (0.100 g, 0.223 mmol), potassium hexacyanoferrate(II) trihydrate (30 mg, 0.06 mmol), sodium carbonate (0.047 g, 0.45 mmol) and palladium acetate (2 mg, 0.01 mmol) in N,N-dimethylacetamide (1.2 mL) was stirred at 120° C. for 2 h. LCMS showed the reaction was complete. The reaction was diluted with EtOAc, washed with water, brine, dried over MgSO4, filtered, and concentrated. The residue was purified by chromatography on silica gel with MeOH in methylene chloride (0-10%) to afford the desired product (0.10 g, 60%). LCMS: (M+H)=395.0.

後処理

  1. washwashed with water, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel with MeOH in methylene chloride (0-10%)

出典と根拠

ORDレコード
ord-b8d3400d2b984ca4a00bf82fa8280be6
出典データセット
uspto-grants-2010_08
特許番号
US07767675B2

反応ノート

読み込み中…