Ethyl Bromide → HCID 67397451, compound

HRID 914467Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][NH:9][CH:10]=1)=[O:5])[CH3:2].I[C:12]1[S:13][CH:14]=[CH:15][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].BrCC>CS(C)=O.C(OCC)(=O)C.[Cu]>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)[CH:10]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 150 °C

Procedure

1H-Pyrazole-4-carboxylic acid ethyl ester (7.0 g) and 2-iodothiophene (10.5 g) were dissolved in DMSO (50 mL), potassium carbonate (6.91 g) and copper powder (31.7 mg) were added, and the mixture was stirred at 150° C. for 6 hr. The reaction mixture was cooled to 80° C., bromoethane (2 mL) was added, and the mixture was stirred for 2 hr and cooled to room temperature. The reaction mixture was diluted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=9:1) to give 1-(2-thienyl)-1H-pyrazole-4-carboxylic acid ethyl ester (2.23 g) as a white solid. The obtained compound was subjected to reactions in the same manner as in Reference Examples 17 to 18 to give the title compound.

Workup

temperatureThe reaction mixture was cooled to 80° C.
stirringthe mixture was stirred for 2 hr
temperaturecooled to room temperature
washThe organic layer was washed with water
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=9:1)

Sources & evidence

ORD record: ord-114bd64eadf24ed4b4b03b40bb00ba63
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026370B2

Reaction notes

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