Dimethylformamide → 1-(Tetrahydrofuran-3-YL)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-pyrazole

HRID 2090435Notes

Reaction equation

HRID 2090435 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.[H-].[Na+].CN(C)C=O.CS(O[CH:27]1[CH2:31][CH2:30][O:29][CH2:28]1)(=O)=O>C(OCC)(=O)C>[O:29]1[CH2:30][CH2:31][CH:27]([N:12]2[CH:13]=[C:9]([B:4]3[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:14])([CH3:1])[O:3]3)[CH:10]=[N:11]2)[CH2:28]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 15278452Oxolan-3-yl methanesulfonate

Product 1

HCID 592317121-(Tetrahydrofuran-3-YL)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-pyrazoleYield 71.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.1 g, 0.5 mmol), sodium hydride (31 mg, 0.77 mmol) in N,N-dimethylformamide (1 mL, 10 mmol) was stirred at r.t. for 10 min, then, tetrahydrofuran-3-yl methanesulfonate (86 mg, 0.52 mmol) was added. The resulting mixture was stirred at 110° C. for 2 hours. After cooling it was diluted with ethyl acetate, washed with water twice, brine once; dried over Na2SO4. After filtration the filtrate was concentrated to yield 95 mg of product which was directly used in the next step reaction without further purification.

Workup

  1. stirringThe resulting mixture was stirred at 110° C. for 2 hours
  2. temperatureAfter cooling it
  3. washwashed with water twice
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration the filtrate
  6. concentrationwas concentrated

Sources & evidence

ORD record
ord-1948aef0078c4a13bf6ceaa30d630477
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

Loading…