Potassium Carbonate → methyl 4-(1-ethyl-1H-pyrazol-5-yl)-5-methyl-2-furancarboxylate

HRID 1961329Notes

Reaction equation

[CH2:1]([N:3]1[C:7](B2OC(C)(C)C(C)(C)O2)=[CH:6][CH:5]=[N:4]1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[C:24]1[CH:25]=[C:26]([C:30]([O:32][CH3:33])=[O:31])[O:27][C:28]=1[CH3:29]>COCCOC.O.C(Cl)Cl.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH2:1]([N:3]1[C:7]([C:24]2[CH:25]=[C:26]([C:30]([O:32][CH3:33])=[O:31])[O:27][C:28]=2[CH3:29])=[CH:6][CH:5]=[N:4]1)[CH3:2]

Participants

Conditions

Temperature: 72 °C

Procedure

To a 100 mL sealed flask was added 1-ethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (2.2 g, 9.91 mmol), potassium carbonate (2.84 g, 20.54 mmol), methyl 4-bromo-5-methyl-2-furancarboxylate (1.5 g, 6.85 mmol) and BIS(TRI-T-BUTYLPHOSPHINE)PALLADIUM(0) (0.175 g, 0.34 mmol) in 1,2-dimethoxyethane (6 mL) and H2O (1 mL). After stirring for 2 h at 72° C., the reaction solution was diluted with DCM (50 mL) and washed with H2O. The organic layer was dried Na2SO4, filtered and concentrated. The residue was purified on silica gel [EtOAC/hexanes, 10-30%] to give the product [1.1 g, 68.6%] as an off white solid: LC-MS (ES) m/z 235 (M+H)+.

Workup

customTo a 100 mL sealed flask
washwashed with H2O
filtrationfiltered
concentrationconcentrated
customThe residue was purified on silica gel [EtOAC/hexanes, 10-30%]
customto give the product [1.1 g, 68.6%] as an off white solid

Sources & evidence

ORD record: ord-36070602c8ac4796b1e4d04558ef6e6b
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410158B2

Reaction notes

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