3-(2-methyl-2H-indazol-4-yl)prop-2-yn-1-ol → (2Z)-3-(2-methyl-2H-indazol-4-yl)prop-2-en-1-ol

HRID 1639765

Reaction equation

[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([CH:5]=[CH:6][CH:7]=[C:8]2[C:11]#[C:12][CH2:13][OH:14])=[N:3]1>CO.C(=O)([O-])[O-].[Ca+2].[Pd+2].C(=O)([O-])[O-]>[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([CH:5]=[CH:6][CH:7]=[C:8]2/[CH:11]=[CH:12]\[CH2:13][OH:14])=[N:3]1

Participants

Conditions

Temperature: -10 °C

Procedure

Under hydrogen gas atmosphere, a mixture of 3-(2-methyl-2H-indazol-4-yl)prop-2-yn-1-ol (50.0 mg, 0.269 mmol) and 5% palladium-calcium carbonate (lead poisoned, Lindlar catalyst, 5 mg) in methanol (3 mL) was stirred at −10° C. for 90 min, and filtered. The solvent was evaporated under reduced pressure. The residue was washed with diisopropyl ether to give the title compound (41.6 mg, yield 82%).

Workup

filtrationfiltered
customThe solvent was evaporated under reduced pressure
washThe residue was washed with diisopropyl ether

Sources & evidence

ORD record: ord-021d794e88834ceeb678342fd71f35ed
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08110585B2

Linked notes

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