Propargyl alcohol → 3-(2-methyl-2H-indazol-4-yl)prop-2-yn-1-ol

HRID 1639764Notes

Reaction equation

Br[C:2]1[C:3]2[C:7]([CH:8]=[CH:9][CH:10]=1)=[N:6][N:5]([CH3:11])[CH:4]=2.[CH2:12]([OH:15])[C:13]#[CH:14]>C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:11][N:5]1[CH:4]=[C:3]2[C:7]([CH:8]=[CH:9][CH:10]=[C:2]2[C:14]#[C:13][CH2:12][OH:15])=[N:6]1

Participants

Conditions

Temperature: 70 °C

Procedure

Under argon gas atmosphere, a mixture of 4-bromo-2-methyl-2H-indazole (1.00 g, 4.74 mmol), propargyl alcohol (1.10 mL, 18.9 mmol) and bis(triphenylphosphine)palladium(II) dichloride (665 mg, 0.947 mmol) in triethylamine (47 mL) was stirred at 70° C. for 14 hr, and concentrated under reduced pressure. The residue was dissolved in ethyl acetate, and insoluble material was filtered off. The filtrate was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane=70/30→100/0) and the obtained crudely purified product was washed with ethyl acetate to give the title compound (403 mg, yield 46%).

Workup

concentrationconcentrated under reduced pressure
dissolutionThe residue was dissolved in ethyl acetate
filtrationinsoluble material was filtered off
washThe filtrate was washed with water and saturated brine
dry with materialdried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane=70/30→100/0)
customthe obtained crudely purified product
washwas washed with ethyl acetate

Sources & evidence

ORD record: ord-7ea6a80475464285ac61c79dbf2a12ea
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08110585B2

Reaction notes

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