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 417927Notes

Reaction equation

HRID 417927 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([O:25][CH2:24]1)[CH3:23]>>[CH3:21][C:22]([OH:25])([CH3:24])[CH2:23][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

4

Reactant 3

HCID 10796Cesium carbonateHCID 11208Isobutylene oxideHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 582041312-methyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propan-2-olYield 87%

Conditions

Temperature
120 °C

Procedure

A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.5 g, 7.73 mmol) and cesium carbonate (0.499 g, 1.34 mmol) in isobutylene oxide (15 mL) was heated to 120° C. under microwave irradiation for 30 minutes. It was cooled to r.t., filtered and concentrated in vacuo to give the title compound (1.79 g, 87%) as a cream solid. δH (CDCl3) 1.15 (6H, s), 1.33 (12H, s), 3.97 (1H, s), 4.07 (2H, s), 7.69 (1H, s), 7.82 (1H, s). LCMS (ES+) 269/269 (M+H)+.

Workup

  1. temperatureIt was cooled to r.t.
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1763e8c402624037833ac45a779d274d
Source dataset
uspto-grants-2012_01
Patent number
US08093238B2

Reaction notes

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