Potassium Hydroxide → 3-bromo-2-methyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole
Reaction equation
[Br:1][C:2]1[C:3]([CH3:11])=[N:4][NH:5][C:6]=1[CH2:7][CH2:8][CH2:9]Cl.[OH-].[K+]>C(O)(C)C.O>[Br:1][C:2]1[C:3]([CH3:11])=[N:4][N:5]2[CH2:9][CH2:8][CH2:7][C:6]=12Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 4-bromo-5-(3-chloro-propyl)-3-methyl-1H-pyrazole (2.42 g, 10.2 mmol) in isopropyl alcohol (35 mL) was added KOH (0.86 g, 15.3 mmol) dissolved in water (7 mL). The reaction was heated to reflux for 4 h. After cooling the reaction was partially concentrated, diluted with EtOAc and washed with brine. The organic layer was dried over Na2SO4, filtered and concentrated to give a light yellow oil as the desired product (1.01 g, 5.0 mmol). MS m/z 203.4 (M+H)+.
Workup
- temperatureThe reaction was heated
- temperatureto reflux for 4 h
- temperatureAfter cooling the reaction
- concentrationwas partially concentrated
- additiondiluted with EtOAc
- washwashed with brine
- dry with materialThe organic layer was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-afe1c77df44c433591b865d1cdc7202e
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08598217B2
Reaction notes
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