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Cesium fluoride → 6-((6-(4-methyl-1H-imidazol-1-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline

HRID 15990
Notes
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Reaction equation

HRID 15990 reaction equation
Br[C:2]1[N:7]=[C:6]2[N:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][CH:16]=[CH:15]4)[N:9]=[N:10][C:5]2=[N:4][CH:3]=1.[CH3:22][C:23]1[N:24]=[CH:25][NH:26][CH:27]=1.[F-].[Cs+]>C(#N)C.O>[CH3:22][C:23]1[N:24]=[CH:25][N:26]([C:2]2[N:7]=[C:6]3[N:8]([CH2:11][C:12]4[CH:13]=[C:14]5[C:19](=[CH:20][CH:21]=4)[N:18]=[CH:17][CH:16]=[CH:15]5)[N:9]=[N:10][C:5]3=[N:4][CH:3]=2)[CH:27]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 547756086-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinolineHCID 178418800HCID 178418800, compound

Product 1

HCID 248518386-((6-(4-methyl-1H-imidazol-1-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinolineYield 56%

Reagents, catalysts & solvents 2

HCID 962Water
Solvent
HCID 6342AcetonitrileSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 6-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (50 mg, 0.15 mmol), 4-methyl-1H-imidazole (36 mg, 0.44 mmol) and CsF (25 mg, 0.16 mmol) in acetonitrile (1.45 mL) was heated in a microwave to 160° C. for 20 minutes. The reaction was diluted with water (5 mL) and the resulting suspension was filtered. The precipitate was washed with water and then purified by column chromatography using gradient elution with methanol and dichloromethane to afford 6-((6-(4-methyl-1H-imidazol-1-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (28 mg, yield 56%)

Workup

  1. filtrationthe resulting suspension was filtered
  2. washThe precipitate was washed with water
  3. custompurified by column chromatography
  4. washelution with methanol and dichloromethane

Sources & evidence

ORD record
ord-c0952ee84e994226b7dcb2797003c9a7
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07732604B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes