HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Water → 1-Ethyl-3-{5-[(3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)oxy]pyridin-2-yl}-1H-pyrazolo[4,3-b]pyridine

HRID 573326
Notes
Print preview

Reaction equation

HRID 573326 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[N:4]=[C:3]1S(C)(=O)=O.[CH2:15]([N:17]1[C:25]2[C:20](=[N:21][CH:22]=[CH:23][CH:24]=2)[C:19]([C:26]2[N:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)=[N:18]1)[CH3:16].[H-].[Na+].O>CN(C=O)C>[CH2:15]([N:17]1[C:25]2[C:20](=[N:21][CH:22]=[CH:23][CH:24]=2)[C:19]([C:26]2[CH:27]=[CH:28][C:29]([O:32][C:3]3[N:2]([CH3:1])[C:6]4=[N:7][CH:8]=[CH:9][CH:10]=[C:5]4[N:4]=3)=[CH:30][N:31]=2)=[N:18]1)[CH3:16]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 585773713-Methyl-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridineHCID 1363976906-(1-Ethyl-1H-pyrazolo[4,3-b]pyridin-3-yl)pyridin-3-ol

Product 1

HCID 667281201-Ethyl-3-{5-[(3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)oxy]pyridin-2-yl}-1H-pyrazolo[4,3-b]pyridineYield 36.2%

Reagents, catalysts & solvents

1
HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 3-methyl-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridine (90 mg) and 6-(1-ethyl-1H-pyrazolo[4,3-b]pyridin-3-yl)pyridin-3-ol (68 mg) in DMF (1 mL) was added NaH (60% in oil, 18.11 mg), and the mixture was stirred at 100° C. for 1 h. The mixture was heated at 180° C. for 30 min under microwave irradiation. The mixture was poured into water and extracted with AcOEt. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (AcOEt/hexane). The eluent was evaporated and the residue was crystallized from EtOH/hexane to give the title compound (38.1 mg).

Workup

  1. temperatureThe mixture was heated at 180° C. for 30 min under microwave irradiation
  2. extractionextracted with AcOEt
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (AcOEt/hexane)
  8. customThe eluent was evaporated
  9. customthe residue was crystallized from EtOH/hexane

Sources & evidence

ORD record
ord-af457ea6be4b47148d654058b1651c55
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09029536B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes