Potassium Carbonate → ethyl 3-(2,4-difluorophenyl)-1-(3-hydroxybutan-2-yl)-1H-thieno[2,3-c]pyrazole-5-carboxylate

HRID 1047619Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]2[CH:16]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[S:14][C:11]=2[NH:12][N:13]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:28][C@@H:29]1[O:31][C@H:30]1[CH3:32]>CN(C)C=O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]2[CH:16]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[S:14][C:11]=2[N:12]([CH:29]([CH:30]([OH:31])[CH3:32])[CH3:28])[N:13]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of ethyl 3-(2,4-difluorophenyl)-1H-thieno[2,3-c]pyrazole-5-carboxylate (200 mg, 0,649 mmol) and potassium carbonate (448 mg, 3.24 mmol) in N,N-dimethylformamide (6.5 mL) was added trans-dimethyloxirane (140 mg, 1.95 mmol). The reaction mixture was stirred at 100° C. for 18 hr. The mixture was cooled to ambient temperature. Purification by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.05% ammonium hydroxide) gave the title compound (134 mg). LC-MS [M+1]=381.2.

Workup

temperatureThe mixture was cooled to ambient temperature
customPurification by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.05% ammonium hydroxide)

Sources & evidence

ORD record: ord-7d34cfa90bfd42159b4b38b41fa05380
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569512B2

Reaction notes

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