Potassium Carbonate → HCID 57826920, compound

HRID 1845494Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:10]([O:12][CH3:13])=[O:11])[S:5][C:6]=1[CH2:7][CH2:8][CH3:9].C(=O)([O-])[O-].[K+].[K+].[CH3:20][N:21]1[C:25](B2OC(C)(C)C(C)(C)O2)=[CH:24][CH:23]=[N:22]1>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>[CH3:20][N:21]1[C:25]([C:2]2[CH:3]=[C:4]([C:10]([O:12][CH3:13])=[O:11])[S:5][C:6]=2[CH2:7][CH2:8][CH3:9])=[CH:24][CH:23]=[N:22]1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of methyl 4-bromo-5-propyl-2-thiophenecarboxylate (1.0 g, 3.80 mmol), potassium carbonate (2.63 g, 19.00 mmol), 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.949 g, 4.56 mmol) [prepared according to Preparation 7] and bis(tri-t-butylphosphine)palladium(0) (0.097 g, 0.19 mmol) were combined in a sealed tube and stirred at 80° C. for 1 h. The reaction contents were then partitioned between H2O-DCM and the aqueous phase was washed several times with DCM. The combined organic fractions were dried over Na2SO4 and concentrated and purified by column chromatography (10-50% EtOAc in hexanes) affording methyl 4-(1-methyl-1H-pyrazol-5-yl)-5-propyl-2-thiophenecarboxylate (1.07 g, 3.76 mmol, 99% yield) as a yellow oil: LCMS (ES) m/e 265 (M+H)+.

Workup

customThe reaction contents
customwere then partitioned between H2O-DCM
washthe aqueous phase was washed several times with DCM
dry with materialThe combined organic fractions were dried over Na2SO4
concentrationconcentrated
custompurified by column chromatography (10-50% EtOAc in hexanes)

Sources & evidence

ORD record: ord-ea29c48afa3b45f8a6dee93ca62ba3fd
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946278B2

Reaction notes

Loading…