Cesium carbonate → 4-(4-iodo-1H-pyrazol-1-yl)tetrahydro-2H-thiopyran 1,1-dioxide

HRID 1485766Notes

Reaction equation

[I:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.CS(O[CH:12]1[CH2:17][CH2:16][S:15](=[O:19])(=[O:18])[CH2:14][CH2:13]1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)([O-])C.[K+]>CN(C=O)C.O>[I:1][C:2]1[CH:3]=[N:4][N:5]([CH:12]2[CH2:17][CH2:16][S:15](=[O:19])(=[O:18])[CH2:14][CH2:13]2)[CH:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of 4-iodo-1H-pyrazole (1.00 g, 5.16 mmol), 1,1-dioxidotetrahydro-2H-thiopyran-4-yl methanesulfonate (1.77 g, 7.73 mmol) and cesium carbonate (2.52 g, 7.73 mmol) in DMF (10 mL) was heated to 80° C. for 2 h. The reaction was cooled to room temperature, and potassium tert-butoxide (0.578 g, 5.16 mmol) was added. The reaction mixture stirred at room temperature for 30 minutes and then water (30 mL) was added. The mixture stirred for 4 h and was then filtered. The filter cake was washed with water (10 mL) and dried in vacuo to afford 4-(4-iodo-1H-pyrazol-1-yl)tetrahydro-2H-thiopyran 1,1-dioxide (1.00 g, 60%) as an off-white solid. MS (ESI, pos. ion) m/z 327 [M+H]+.

Workup

temperatureThe reaction was cooled to room temperature
stirringThe mixture stirred for 4 h
filtrationwas then filtered
washThe filter cake was washed with water (10 mL)
customdried in vacuo

Sources & evidence

ORD record: ord-63614126339b457ab75f9304577a61f0
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422281B2

Reaction notes

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