Tetrahydrofuran → 1-(5,8-dioxaspiro[3.4]oct-2-yl)-5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
Reaction equation
[CH2:1]1[C:4]2([O:8][CH2:7][CH2:6][O:5]2)[CH2:3][CH:2]1[N:9]1[C:13]([CH3:14])=[C:12](I)[CH:11]=[N:10]1.C1COCC1.C([Mg]Cl)(C)C.CO[B:28]1[O:32][C:31]([CH3:34])([CH3:33])[C:30]([CH3:36])([CH3:35])[O:29]1.[NH4+].[Cl-]>>[CH2:1]1[C:4]2([O:8][CH2:7][CH2:6][O:5]2)[CH2:3][CH:2]1[N:9]1[C:13]([CH3:14])=[C:12]([B:28]2[O:32][C:31]([CH3:34])([CH3:33])[C:30]([CH3:36])([CH3:35])[O:29]2)[CH:11]=[N:10]1Participants
6
Reactant 5
Product 1
Procedure
To a solution of 1-(5,8-dioxaspiro[3.4]oct-2-yl)-4-iodo-5-methyl-1H-pyrazole (50.0 mg, 0.156 mmol) in THF (3 mL, 40 mmol) at was added 2 M isopropylmagnesium chloride in THF (0.23 mL, 0.46 mmol), and the mixture was stirred at rt for 1 h. The reaction was quenched with 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.10 mL, 0.62 mmol) and allowed to stir at rt for 1 h. Sat. NH4Cl was added, and the organic solvent was removed in vacuo. The material was extracted with DCM and water. The organic layer was concentrated in vacuo to afford the title compound as a white solid. The material was used in the next step without further purification.
Workup
- stirringto stir at rt for 1 h
- customthe organic solvent was removed in vacuo
- extractionThe material was extracted with DCM and water
- concentrationThe organic layer was concentrated in vacuo
Sources & evidence
- ORD record
- ord-f8823ef991ed4909b3f6eb46479fdb26
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08445510B2
Reaction notes
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