Triethyl borate → HCID 59321066, compound

HRID 341175Notes

Reaction equation

HRID 341175 reaction equation
C[Li].[CH3:3][N:4]([CH3:14])[S:5]([N:8]1[CH:12]=[C:11](Br)[CH:10]=[N:9]1)(=[O:7])=[O:6].[B:15](OCC)([O:19]CC)[O:16]CC>C1COCC1>[CH3:3][N:4]([CH3:14])[S:5]([N:8]1[CH:12]=[C:11]([B:15]([OH:19])[OH:16])[CH:10]=[N:9]1)(=[O:7])=[O:6]

Participants

5

Reactant 3

HCID 9009Triethyl borateHCID 4640412HCID 4640412, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 59321066HCID 59321066, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl lithium (1.6M in Et2O, 12.2 ml, 19.5 mmol) was added to a stirred solution of 4-bromo-pyrazole-1-sulfonic acid dimethylamide (3.18 g, 14.9 mmol) and triethyl borate (3.80 ml, 22.3 mmol) in anhydrous THF (40 ml), such that the internal temperature remained >-60° C. After 30 min, the reaction was allowed to warm to room temperature and stirred for 18 h. The reaction was quenched with 2N HCl (25 ml), then extracted with EtOAc (×3). The organic extracts were combined, dried (Na2SO4), filtered and the solvent removed in vacuo. The material was purified by silica column chromatography to afford a colourless gum (2.1 g). MS: [M+H]+=220

Workup

  1. customremained >-60° C
  2. customThe reaction was quenched with 2N HCl (25 ml)
  3. extractionextracted with EtOAc (×3)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customThe material was purified by silica column chromatography

Sources & evidence

ORD record
ord-01780225dd8141b0bfc79526c029385c
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

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