Triethylamine → 3-bromo-4-(chloromethyl)-1-tert-pentyl-1H-pyrazole
Reaction equation
[Br:1][C:2]1[C:6]([CH2:7]O)=[CH:5][N:4]([C:9]([CH2:12][CH3:13])([CH3:11])[CH3:10])[N:3]=1.C(N(CC)CC)C.CS([Cl:25])(=O)=O>ClCCl.C(OCC)(=O)C>[Br:1][C:2]1[C:6]([CH2:7][Cl:25])=[CH:5][N:4]([C:9]([CH2:12][CH3:13])([CH3:11])[CH3:10])[N:3]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
A solution of (3-bromo-1-tert-pentyl-1H-pyrazol-4-yl)methanol (675 mg, 2.73 mmol) in dichloromethane (10 mL) was cooled to 0° C. Triethylamine (0.53 mL, 3.8 mmol) and methanesulfonyl chloride (0.28 mL, 3.6 mmol) were added. The reaction was stirred at 0° C. for 15 minutes, then warmed to room temperature and stirred for 1.5 hours. The reaction was diluted with ethyl acetate, washed with water and brine, dried over sodium sulfate, filtered, and concentrated to give the title compound (725 mg, 100%) as a clear oil. 1H NMR (400 MHz, CDCl3, δ): 7.48 (s, 1H), 4.47 (s, 2H), 1.86 (q, J=7.48 Hz, 2H), 1.52 (s, 6H), 0.69 (m, 3H).
Workup
- temperaturewarmed to room temperature
- stirringstirred for 1.5 hours
- washwashed with water and brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-3b898b5b4a8c46b39b86a33d64b339b9
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08993586B2
Reaction notes
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