Dimethylformamide → 1-(3-(benzyloxy)cyclobutyl)-4-iodo-1H-pyrazole
Reaction equation
[I:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.CN(C)C=O.CS(O[CH:17]1[CH2:20][CH:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:18]1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>O>[CH2:22]([O:21][CH:19]1[CH2:18][CH:17]([N:4]2[CH:3]=[C:2]([I:1])[CH:6]=[N:5]2)[CH2:20]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1Participants
6
Conditions
- Temperature
- 80 °C
Procedure
A 250-mL round-bottom flask was charged with 4-iodo-1H-pyrazole (1.97 g, 10.2 mmol), N,N-dimethylformamide (20 mL), 3-(benzyloxy)cyclobutyl methanesulfonate (2.60 g, 10.2 mmol) and cesium carbonate (9.75 g, 29.9 mmol), and the resulting mixture stirred overnight at 80° C. The reaction mixture was cooled to room temperature, poured into water (50 mL), and extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to afford 1-(3-(benzyloxy)cyclobutyl)-4-iodo-1H-pyrazole (3.00 g, 83%) as yellow oil. MS (ESI, pos. ion) m/z 355 [M+H]+.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- extractionextracted with ethyl acetate (3×50 mL)
- washThe combined organic layers were washed with brine (50 mL)
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-8d180dce50fe46a69cf4b81ec11c128c
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09388161B2
Reaction notes
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