Sodium hydride → HCID 59402394, compound

HRID 2090438Notes

Reaction equation

HRID 2090438 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.CS(O[CH2:20][CH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1)(=O)=O.[H-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH:21]1([CH2:20][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)[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 15712513Cyclopentylmethyl methanesulfonate

Product 1

HCID 59402394HCID 59402394, compoundYield 79.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.1 g, 0.5 mmol), cyclopentylmethyl methanesulfonate (0.10 g, 0.58 mmol), and sodium hydride (31 mg, 0.77 mmol) in N,N-dimethylformamide (1 mL) was stirred at 110° C. for 2 h. 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 0.11 g of the product which was directly used in the next step reaction without further purification.

Workup

  1. temperatureAfter cooling it
  2. washwashed with water twice
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration the filtrate
  5. concentrationwas concentrated

Sources & evidence

ORD record
ord-3d40486670a84a2487ea732554f373c3
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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