Cesium carbonate → 1-[(2S)-1,4-Dioxan-2-ylmethyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

HRID 1428126Notes

Reaction equation

HRID 1428126 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+].CS(O[CH2:26][C@H:27]1[CH2:32][O:31][CH2:30][CH2:29][O:28]1)(=O)=O>O1CCOCC1>[O:28]1[CH2:29][CH2:30][O:31][CH2:32][C@@H:27]1[CH2:26][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

5

Reactant 3

HCID 10796Cesium carbonateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 86609782(2R)-1,4-dioxan-2-ylmethyl methanesulfonate

Product 1

HCID 867000791-[(2S)-1,4-Dioxan-2-ylmethyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (2.5 g) was added to a suspension of cesium carbonate (2.50 g) in 1,4-dioxane (30 ml). After stirring, (2R)-1,4-dioxan-2-ylmethyl methanesulfonate (2.78 g) was added and the mixture was stirred at 90° C. for four hours. After leaving to cool, the reaction solution was filtered, and the filtrate was concentrated. The residue was purified by silica gel column chromatography [chloroform:methanol=19:1 (v/v)] to give 3.79 g of the title compound.

Workup

  1. stirringthe mixture was stirred at 90° C. for four hours
  2. customAfter leaving
  3. temperatureto cool
  4. filtrationthe reaction solution was filtered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by silica gel column chromatography [chloroform:methanol=19:1 (v/v)]

Sources & evidence

ORD record
ord-d556cfaa76c244e19fd60fcfdf54ce32
Source dataset
uspto-grants-2015_01
Patent number
US08933103B2

Reaction notes

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