Tetrahydrofuran → 1-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
Reaction equation
[CH3:1][C:2]1([CH3:16])[O:6][C@H:5]([CH2:7][N:8]2[C:12]([CH3:13])=[C:11](I)[C:10]([CH3:15])=[N:9]2)[CH2:4][O:3]1.C1COCC1.C([Mg]Cl)(C)C.CO[B:29]1[O:33][C:32]([CH3:35])([CH3:34])[C:31]([CH3:37])([CH3:36])[O:30]1>>[CH3:1][C:2]1([CH3:16])[O:6][C@H:5]([CH2:7][N:8]2[C:12]([CH3:13])=[C:11]([B:29]3[O:33][C:32]([CH3:35])([CH3:34])[C:31]([CH3:37])([CH3:36])[O:30]3)[C:10]([CH3:15])=[N:9]2)[CH2:4][O:3]1Participants
5
Reactant 4
Product 1
Procedure
To a solution of 1-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-4-iodo-3,5-dimethyl-1H-pyrazole (180.0 mg, 0.5354 mmol) in THF (5 mL, 60 mmol) was added 2 M isopropylmagnesium chloride in THF (0.5354 mL, 1.071 mmol) at rt, and the mixture was stirred for 10 min. 2-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.2632 mL, 1.606 mmol) was added, and the mixture stirred at rt for 20 min. The reaction was quenched with sat. NH4Cl, and the organic solvent was removed in vacuo. The material was extracted with DCM and water, and the organic layer was concentrated in vacuo to afford the title compound as a clear oil. The material was used in the next step without further purification.
Workup
- stirringthe mixture stirred at rt for 20 min
- customThe reaction was quenched with sat. NH4Cl
- 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-5e7ece3f85c641d380dc18ae4f67260c
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08445510B2
Reaction notes
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