Cesium carbonate → 2-[(1-Methyl-1H-pyrazol-5-yl)methoxy]-5-(trifluoromethyl)pyridine

HRID 238392

Reaction equation

[CH3:1][N:2]1[C:6]([CH2:7][OH:8])=[CH:5][CH:4]=[N:3]1.Cl[C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][N:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(P(C(C)(C)C)C1C=CC2C(=CC=CC=2)C=1C1C2C(=CC=CC=2)C=CC=1)(C)(C)C>C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[CH3:1][N:2]1[C:6]([CH2:7][O:8][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][N:11]=2)=[CH:5][CH:4]=[N:3]1

Participants

Conditions

Temperature: 100 °C

Procedure

Under a nitrogen atmosphere, a mixture of (1-methyl-1H-pyrazol-5-yl)methanol (200 mg), 2-chloro-5-(trifluoromethyl)pyridine (389 mg), palladium(II) acetate (40 mg), cesium carbonate (870 mg), rac-2-(di-t-butylphosphino)-1,1′-binaphthyl (71 mg) and toluene (9.0 mL) was stirred at 100° C. for 2.5 hours. Thereafter, the reaction solution was diluted with diethyl ether, and was then filtrated with Celite. The filtrate was concentrated under a reduced pressure. The residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=85:15 to 50:50), so as to obtain the title compound (310 mg) in the form of a light yellow oily substance.

Workup

filtrationwas then filtrated with Celite
concentrationThe filtrate was concentrated under a reduced pressure
customThe residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=85:15 to 50:50)

Sources & evidence

ORD record: ord-8c6de477712d45f29b5d77c8d2732461
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642626B2

Linked notes

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