Cesium carbonate → 2-methyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propan-2-ol

HRID 1024378Notes

Reaction equation

[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[O:3]1.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:21][C:22]1([CH3:25])[CH2:24][O:23]1>C(Cl)Cl>[CH3:21][C:22]([OH:23])([CH3:25])[CH2:24][N:12]1[CH:13]=[C:9]([B:4]2[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:14])([CH3:1])[O:3]2)[CH:10]=[N:11]1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (500 mg, 2.57 mmol), Cs2CO3 (840 mg, 2.57 mmol) and 2,2-dimethyloxirane (2 mL) was heated in a sealed vial at 120° C. for 3 minutes with stirring in a Smith Synthesizer microwave oven (at 300 W), then allowed to cool and diluted with CH2Cl2. The resulting suspension was filtered, and the filtrate was concentrated to give the title compound.

Workup

temperatureto cool
filtrationThe resulting suspension was filtered
concentrationthe filtrate was concentrated

Sources & evidence

ORD record: ord-db769f39d61d401ab0174f27bd3ce4f8
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722890B2

Reaction notes

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