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

HRID 500242노트

반응식

HRID 500242 반응식
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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 161067Potassium ferrocyanide trihydrate촉매HCID 167845palladium(II) acetate촉매HCID 8857Ethyl Acetate용매

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온도
120 °C

실험 절차

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.

후처리

  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%)

출처 및 근거

ORD 기록
ord-b8d3400d2b984ca4a00bf82fa8280be6
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07767675B2

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