Ethyl Acetate → HCID 67260822, compound

HRID 511344Notes

Reaction equation

HRID 511344 reaction equation
[B:1]1([C:10]2[NH:14][N:13]=[CH:12][CH:11]=2)[O:5]C(C)(C)C(C)(C)[O:2]1.[C:15]([Si:19]([O:22][CH2:23][CH2:24]I)([CH3:21])[CH3:20])([CH3:18])([CH3:17])[CH3:16].C([O-])([O-])=O.[Cs+].[Cs+].CCOC(C)=O>CN(C=O)C.O>[Si:19]([O:22][CH2:23][CH2:24][N:13]1[CH:12]=[CH:11][C:10]([B:1]([OH:2])[OH:5])=[N:14]1)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:21])[CH3:20]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 11129873tert-Butyl(2-iodoethoxy)dimethylsilaneHCID 219315391H-Pyrazole, 5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-

Product 1

HCID 67260822HCID 67260822, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

In a sealed tube, a suspension of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)-pyrazole (100.0 mg, 0.5154 mmol), tert-butyl-(2-iodoethoxy)-dimethylsilane (196 mg, 0.685 mmol), and Cs2CO3 (271 mg, 0.832 mmol) in DMF (3 mL) was stirred at 100° C. for 16 h. The sample was suspended between EtOAc and water and the layers were separated. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo, giving the title material as the boronic acid, as a yellow oil (203.4 mg). MS (ES+): m/z 270.18/271.13/272.15 (19/79/15) [MH+]. HPLC: tR=3.33 min (CAD, ZQ3, polar—5 min).

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5f6d142848174ee7a1a194b2ecbdfb94
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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