Sodium Iodide → HCID 67441204, compound

HRID 1255748Notes

Reaction equation

HRID 1255748 reaction equation
Br[CH2:2][CH:3]1[CH2:5][CH2:4]1.[I-].[Na+].[OH:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][C:18]1[CH:27]=[CH:26][C:21]2[B:22]([OH:25])[O:23][CH2:24][C:20]=2[CH:19]=1)[C:12]#[N:13].[H-].[Na+]>O.CN(C)C=O>[CH:5]1([CH2:4][O:8][C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=2[O:17][C:18]2[CH:27]=[CH:26][C:21]3[B:22]([OH:25])[O:23][CH2:24][C:20]=3[CH:19]=2)[C:12]#[N:13])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 67439736HCID 67439736, compound

Product 1

HCID 67441204HCID 67441204, compoundYield 37.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of bromomethyl cyclopropane (0.544 mL, 5.61 mmol), sodium iodide (4.20 g, 28.05 mmol), and N,N-dimethylformamide (30 mL) under a nitrogen balloon were stirred at 70° C. for 3 hours. The reaction was cooled to room temperature and 3-hydroxy-4-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yloxy)benzonitrile (0.500 g, 1.87 mmol) and more N,N-dimethylformamide (30 mL) was added. The reaction was cooled to 0° C. in an ice water bath and sodium hydride (0.224 g, 5.61 mmol) was added. The reaction was stirred under nitrogen balloon at 0° C. for 5 minutes and then at room temperature overnight. Water was added to quench excess sodium hydride and the solution was neutralized using 1 M HCl. Water was added and the solution was extracted using ethyl acetate. The organic layer was washed with water, brine, dried over anhydrous sodium sulfate, and filtered. The solvent was removed under reduced pressure. The residue was purified by silica gel column using Combiflash to give 3-(cyclopropylmethoxy)-4-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yloxy)benzonitrile (0.225 g, 37% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.15 (d, J=4.5 Hz, 2H), 0.43 (d, J=7.6 Hz, 2H), 1.06 (septet, J=6.7 Hz, 1H), 3.90, (d, J=6.9 Hz, 1H), 4.91 (s, 2H), 6.95 (m, 2H), 7.13 (d, J=8.2 Hz, 1H), 7.42 (d, J=8.4 Hz, 1H), 7.62 (s, 1H), 7.70 (d, J=8.6 Hz, 1H), 9.12 (s, 1H).

Workup

  1. temperatureThe reaction was cooled to 0° C. in an ice water bath
  2. customat room temperature
  3. customovernight
  4. customto quench excess sodium hydride
  5. additionWater was added
  6. extractionthe solution was extracted
  7. washThe organic layer was washed with water, brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customThe solvent was removed under reduced pressure
  11. customThe residue was purified by silica gel column

Sources & evidence

ORD record
ord-1b285a71acbb4bb0ad79165cd1b1ef3a
Source dataset
uspto-grants-2013_06
Patent number
US08461135B2

Reaction notes

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