Potassium Phosphate, Tribasic → methyl 5-methyl-4-(1-methyl-1H-pyrazol-5-yl)-2-furancarboxylate

HRID 1961237Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[O:5][C:6]=1[CH3:7].[CH3:12][N:13]1[C:17](B2OC(C)(C)C(C)(C)O2)=[CH:16][CH:15]=[N:14]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].P(OC)(OC)OC>[CH3:7][C:6]1[O:5][C:4]([C:8]([O:10][CH3:11])=[O:9])=[CH:3][C:2]=1[C:17]1[N:13]([CH3:12])[N:14]=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 95 °C

Procedure

To a 5 mL sealed flask reactor was added methyl 4-bromo-5-methyl-2-furancarboxylate (1.13 g, 5.16 mmol), 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.31 g, 6.30 mmol) [prepared according to the procedure of Preparation 7], K3PO4 (3.87 g, 18.23 mmol) and Pd2(dba)3 (153 mg, 0.17 mmol) and P(OMe)3 (32 μL, 0.27 mmol) in 1,4-Dioxane (23 mL). The reaction was heated at 95° C. for 4 hours, cooled to room temperature and partitioned between CHCl3/H2O. The organic layer was separated, dried with Na2SO4, adsorbed onto silica and purified via column chromatography (0-15% EtOAc/Hexanes) affording the title compound (967 mg, 4.39 mmol, 85%): LC-MS (ES) m/z=271 (M+H)+.

Workup

customTo a 5 mL sealed flask reactor
customprepared
temperaturecooled to room temperature
custompartitioned between CHCl3/H2O
customThe organic layer was separated
dry with materialdried with Na2SO4
custompurified via column chromatography (0-15% EtOAc/Hexanes)

Sources & evidence

ORD record: ord-47ce5255765d40a28152b324849d75b5
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410158B2

Reaction notes

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