Bromocyclopentane → 1-Cyclopentyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

HRID 2090450Notes

Reaction equation

HRID 2090450 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.[CH:15]1(Br)[CH2:19][CH2:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH:15]1([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)[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 8728BromocyclopentaneHCID 10796Cesium carbonateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 567767301-Cyclopentyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (50 mg, 0.2 mmol), cyclopentyl bromide (46 mg, 0.31 mmol, Aldrich, Cat. No. C115207), and cesium carbonate (250 mg, 0.77 mmol) in acetonitrile (1 mL) was stirred at 90° C. for 2 hours. After cooling it was quenched with water, extracted with ethyl acetate. The extract was washed with water, brine; dried over Na2SO4. After filtration the filtrate was concentrated to yield 40 mg of the product which was directly used in the next step reaction without further purification. LCMS (M+H)+: m/z=263.3

Workup

  1. temperatureAfter cooling it
  2. customwas quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water, brine
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtration the filtrate
  7. concentrationwas concentrated

Sources & evidence

ORD record
ord-e71d4c14de8f4e469f8da2de7dc0f95e
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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