(4-(Benzyloxy)phenyl)hydrazine monohydrochloride → 1-[4-(Benzyloxy)phenyl]-3-ethyl-1H-pyrazolo[3,4-b]pyridine

HRID 572173Notes

Reaction equation

Cl[C:2]1[C:7]([C:8](=O)[CH2:9][CH3:10])=[CH:6][CH:5]=[CH:4][N:3]=1.Cl.[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][NH2:28])=[CH:23][CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C>[CH2:13]([O:20][C:21]1[CH:22]=[CH:23][C:24]([N:27]2[C:2]3=[N:3][CH:4]=[CH:5][CH:6]=[C:7]3[C:8]([CH2:9][CH3:10])=[N:28]2)=[CH:25][CH:26]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 170 °C

Procedure

1-(2-Chloropyridin-3-yl)propan-1-one (600 mg) and [4-(benzyloxy)phenyl]hydrazine hydrochloride (976 mg) were dissolved in ethanol (10 ml), and the mixture was stirred under microwave irradiation at 170° C. for 3 hr, and concentrated. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate) to give the title compound (300 mg). MS (API+): [M+H]+ 330.1.

Workup

concentrationconcentrated
customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-9cc6a8df27f04689872441414797be2b
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029388B2

Reaction notes

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