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 1040205Notes

Reaction equation

[CH3:1][C:2]1([O:5][CH2:4]1)[CH3:3].[CH3:6][C:7]1([CH3:19])[C:11]([CH3:13])([CH3:12])[O:10][B:9]([C:14]2[CH:15]=[N:16][NH:17][CH:18]=2)[O:8]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)C>[CH3:3][C:2]([OH:5])([CH3:1])[CH2:4][N:17]1[CH:18]=[C:14]([B:9]2[O:8][C:7]([CH3:19])([CH3:6])[C:11]([CH3:13])([CH3:12])[O:10]2)[CH:15]=[N:16]1

Participants

Conditions

Temperature: 80 °C

Procedure

Isobutylene oxide (101 μL, 1.13 mmol) was added to a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (200 mg, 1.03 mmol) and cesium carbonate (403 mg, 1.24 mmol) stirring in N,N-dimethylformamide (3.4 mL). The mixture was stirred at 80° C. for 16 h, cooled to room temperature, diluted with diethyl ether, washed with water (3×) and brine, dried over sodium sulfate, filtered, and concentrated to give 2-methyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propan-2-ol (84 mg, 0.31 mmol, 31% yield) as a yellow solid. ESI: [M+H]+ m/z 267.0.

Workup

temperaturecooled to room temperature
washwashed with water (3×) and brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-57df216dc80848df84ef190e68801288
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08551984B2

Reaction notes

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