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

HRID 573270Notes

Reaction equation

[H-].[Na+].[CH2:3]([N:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[N:6]1)[CH3:4].Cl[C:22]1[N:26]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:25]2[CH:35]=[CH:36][CH:37]=[CH:38][C:24]=2[N:23]=1.O>CN(C=O)C>[CH2:3]([N:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]2[CH:19]=[CH:18][C:17]([O:20][C:22]3[N:26]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:33])([CH3:34])[CH3:32])[C:25]4[CH:35]=[CH:36][CH:37]=[CH:38][C:24]=4[N:23]=3)=[CH:16][CH:15]=2)=[N:6]1)[CH3:4]

Participants

Conditions

Temperature: 150 °C

Procedure

NaH (60% in oil, 59 mg) was added portionwise at room temperature to a solution of 4-(1-ethyl-1H-pyrazolo[4,3-b]pyridin-3-yl)phenol (335 mg) in DMF (3.5 mL). After stirring for 30 min, 2-chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazole (416 mg) was added, and the mixture was heated for 2 h at 150° C. under microwave irradiation. The reaction mixture was poured into water and extracted with AcOEt. The extract was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/AcOEt) and crystallized from hexane/AcOEt to give the title compound (530 mg).

Workup

extractionextracted with AcOEt
washThe extract was washed with brine
dry with materialdried over MgSO4
concentrationconcentrated under reduced pressure
customThe residue was purified by basic silica gel column chromatography (hexane/AcOEt)
customcrystallized from hexane/AcOEt

Sources & evidence

ORD record: ord-f051f36c6bcf4edd9076880c98f7c944
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029536B2

Reaction notes

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