Tetrahydrofuran → tert-Butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)acetate

HRID 1499855Notes

Reaction equation

HRID 1499855 reaction equation
CC(C)([O-])C.[K+].C1COCC1.[CH3:12][C:13]1([CH3:25])[C:17]([CH3:19])([CH3:18])[O:16][B:15]([C:20]2[CH:21]=[N:22][NH:23][CH:24]=2)[O:14]1.Br[CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]>CN(C)C=O.C(OCC)(=O)C>[CH3:12][C:13]1([CH3:25])[C:17]([CH3:18])([CH3:19])[O:16][B:15]([C:20]2[CH:24]=[N:23][N:22]([CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH:21]=2)[O:14]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 79177tert-Butyl bromoacetateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 59216326tert-Butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)acetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.0 M Potassium tert-butoxide in THF (2.4 mL, 2.4 mmol) was added to a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.39 g, 2.0 mmol) in N,N-dimethylformamide (6.0 mL) at 0° C. The reaction mixture was stirred at room temperature for 5 min. After cooled to 0° C., to the mixture was added t-butyl bromoacetate (0.5 mL, 3 mmol). The reaction was stirred at room temperature for 2 h, then diluted with ethyl acetate, washed with sat. NaHCO3, water, brine, dried over Na2SO4, filtered and concentrated. The product (0.5 g, 81%) was purified by chromatography eluting with hexanes/EtOAc (max. EtOAc 30%). LCMS calculated for C15H26BN2O4 (M+H)+: m/z=309.2; Found: 309.1

Workup

  1. temperatureAfter cooled to 0° C., to the mixture
  2. stirringThe reaction was stirred at room temperature for 2 h
  3. washwashed with sat. NaHCO3, water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe product (0.5 g, 81%) was purified by chromatography
  8. washeluting with hexanes/EtOAc (max. EtOAc 30%)

Sources & evidence

ORD record
ord-e30fe457d7234565bdec73601527af76
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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