Cesium carbonate → 1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propan-2-ol

HRID 1406306Notes

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

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (500 mg, 2.58 mmoles, 1.0 equiv.), 1-bromopropan-2-ol (358 mg, 2.58 mmoles, 1.0 equiv.), and cesium carbonate (1010 mg, 3.09 mmoles, 1.20 equiv.) in DMF (10 mL) was heated in an oil bath at 80° C. for 16 hours. LCMS indicated the reaction complete. The reaction was filtered and concentrated to dryness under high vacuum to give the desired product (520 mg).

Workup

filtrationThe reaction was filtered
concentrationconcentrated to dryness under high vacuum

Sources & evidence

ORD record: ord-058e4e1017f3475b88c12a09ce263b45
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916593B2

Reaction notes

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