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Dimethylformamide → 3-Ethyl-1-{4-[(1-methyl-1H-benzimidazol-2-yl)oxy]phenyl}-1H-pyrazolo[3,4-b]pyridine

HRID 572175
Notes
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Reaction equation

HRID 572175 reaction equation
[CH2:1]([C:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)[N:4]=1)[CH3:2].[H-].[Na+].CN(C=O)C.Cl[C:27]1[N:31]([CH3:32])[C:30]2[CH:33]=[CH:34][CH:35]=[CH:36][C:29]=2[N:28]=1>CO>[CH2:1]([C:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:27]3[N:31]([CH3:32])[C:30]4[CH:33]=[CH:34][CH:35]=[CH:36][C:29]=4[N:28]=3)=[CH:14][CH:13]=2)[N:4]=1)[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 6630802-chloro-1-methyl-1H-1,3-benzodiazoleHCID 867049834-(3-Ethyl-1H-pyrazolo[3,4-b]pyridin-1-yl)phenol

Product 1

HCID 867049843-Ethyl-1-{4-[(1-methyl-1H-benzimidazol-2-yl)oxy]phenyl}-1H-pyrazolo[3,4-b]pyridineYield 54%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
180 °C

Procedure

To a mixture of 4-(3-ethyl-1H-pyrazolo[3,4-b]pyridin-1-yl)phenol (120 mg), sodium hydride (60% in oil, 21.0 mg) and DMF (5.0 ml) was added 2-chloro-1-methyl-1H-benzimidazole (84 mg), and the mixture was stirred under microwave irradiation at 180° C. for 1 hr. The reaction mixture was diluted with methanol, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (100 mg).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-93ba427892354122881a57cf2b08f8e0
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09029388B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes