Isopropyl iodide → HCID 58292706, compound

HRID 1798249Notes

Reaction equation

HRID 1798249 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([O:12][C:13]3[CH:18]=[N:17][CH:16]=[CH:15][N:14]=3)[CH:9]=[C:10]([OH:11])[C:5]=2[CH:4]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[O:3]1.I[CH:26]([CH3:28])[CH3:27].[H-].[Na+]>CN(C=O)C>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][CH:4]1[O:3][B:2]([OH:1])[C:6]2[CH:7]=[C:8]([O:12][C:13]3[CH:18]=[N:17][CH:16]=[CH:15][N:14]=3)[CH:9]=[C:10]([O:11][CH:26]([CH3:28])[CH3:27])[C:5]1=2)[CH3:24]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 58292578HCID 58292578, compound

Product 1

HCID 58292706HCID 58292706, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of ethyl 2-(1,4-dihydroxy-6-(pyrazin-2-yloxy)-1,3-dihydrobenzo[c][1,2]oxa-borol-3-yl)acetate (100 mg, 0.30 mmol) and 2-iodopropane (154 mg, 0.91 mmol) in DMF (5 mL) was added 60% NaH (4.85 mg, 1.21 mmol) at 0° C. The reaction mixture was stirred at room temperature for 1 h and quenched by slow addition of water (3 mL). The resulting mixture was acidified with 1 N HCl to pH=4 and extracted with EtOAc (2×15 mL). The combined organic layers were washed with water (10 mL) and brine (10 mL), dried over anhydrous Na2SO4 and concentrated in vacuo to give the title compound as a yellow oil (96 mg, yield: 86%).

Workup

  1. customquenched by slow addition of water (3 mL)
  2. extractionextracted with EtOAc (2×15 mL)
  3. washThe combined organic layers were washed with water (10 mL) and brine (10 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aaa130b0b45f472e9fca117977fdad58
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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