Cesium carbonate → 3,5-Dimethyl-1-(5-trifluoromethyl-pyridin-3-yl)-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 1011872Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:12])=[N:8][NH:9][C:10]=1[CH3:11])=[O:5])[CH3:2].Br[C:14]1[CH:15]=[N:16][CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(N(C)C)=O.CCOC(C)=O.[Cu](I)I>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:12])=[N:8][N:9]([C:14]2[CH:15]=[N:16][CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:19]=2)[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

Conditions

Temperature: 160 °C

Procedure

3,5-Dimethyl-1H-pyrazole-4-carboxylic acid ethyl ester (0.10 g, 1 mmol) (prepared as described in Tett 2002, 58, 18, p 3639), 3-bromo-5-trifluoromethyl-pyridine (0.16 g, 1 mmol), copper iodide (0.02 g, 0.2 mmol) and cesium carbonate (1.0 g, 3 mmol) were suspended in DMA (0.5 ml) and heated to 160° C. for 16 h. The reaction was diluted with EtOAc, washed repeatedly with ammonium hydroxide, brine and dried (Na2SO4) and concentrated. The residue was purified by flash column chromatography (EtOAc:n-heptane 1:9-2:8 gradient affording the title compound (0.07 g, 35%) as a yellow oil. MS: 314.2 (MH+).

Workup

washwashed repeatedly with ammonium hydroxide, brine
dry with materialdried (Na2SO4)
concentrationconcentrated
customThe residue was purified by flash column chromatography (EtOAc:n-heptane 1:9-2:8 gradient

Sources & evidence

ORD record: ord-9eef111c3cb747368e7f36c2210fabc2
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977358B2

Reaction notes

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