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

HRID 573272Notes

Reaction equation

[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:21]3=[N:22][CH:23]=[CH:24][CH:25]=[C:20]3[N:19]([CH2:26][CH3:27])[N:18]=2)=[CH:13][CH:12]=1.CI.[C:30]([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH2:26]([N:19]1[C:20]2[C:21](=[N:22][CH:23]=[CH:24][CH:25]=2)[C:17]([C:14]2[CH:15]=[CH:16][C:11]([O:10][C:2]3[N:1]([CH3:30])[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=3)=[CH:12][CH:13]=2)=[N:18]1)[CH3:27]

Participants

Conditions

Temperature: 40 °C

Procedure

A suspension of 3-[4-(1H-benzimidazol-2-yloxy)phenyl]-1-ethyl-1H-pyrazolo[4,3-b]pyridine (150 mg), MeI (0.039 mL), and K2CO3 (117 mg) in DMF (1.5 ml) was stirred overnight at 40° C. 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 crystallized from hexane/AcOEt to give the title compound (128 mg).

Workup

extractionextracted with AcOEt
washThe extract was washed with brine
dry with materialdried over MgSO4
concentrationconcentrated under reduced pressure
customThe residue was crystallized from hexane/AcOEt

Sources & evidence

ORD record: ord-ba3a1f031f6e4d2da0bd0ef5b55b48a5
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029536B2

Reaction notes

Loading…