Sodium hydride → HCID 69640386, compound

HRID 1191636Notes

Reaction equation

HRID 1191636 reaction equation
[Br:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.[H-].[Na+].[C:9]([O:13][C:14]([N:16]1C(C2C=CC(C#N)=CC=2)O1)=[O:15])([CH3:12])([CH3:11])[CH3:10]>CN(C)C=O>[Br:1][C:2]1[N:3]=[CH:4][N:5]([NH:16][C:14](=[O:15])[O:13][C:9]([CH3:12])([CH3:11])[CH3:10])[CH:6]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2725038N-Boc-3-(4-cyanophenyl)oxaziridineHCID 178418934HCID 178418934, compound

Product 1

HCID 69640386HCID 69640386, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Bromo-1H-imidazole (3.2 g, 21.8 mmol) was weighed into a 500 mL round bottomed flask equipped with a magnetic stir bar under a nitrogen atmosphere. Anhydrous N,N-dimethylformamide (DMF, 12 mL) was added and the mixture was placed on ice. After 10 minutes the mixture was treated with sodium hydride (0.840 g, 21.0 mmol 60% dispersion in oil). After 5 minutes, the ice bath was removed and the reaction warmed to room temperature. After 15 minutes of vigorous stirring the ice bath was re-inserted and 3-(4-cyano-phenyl)-oxaziridine-2-carboxylic acid tert-butyl ester (1.92 g, 7.80 mmol) was added. The reaction was vigorously stirred for 5 minutes and the ice bath was removed. After 5 minutes the mixture was diluted with saturated sodium bicarbonate and extracted with ethyl acetate. The organics were washed with dilute sodium carbonate, dried over sodium sulfate, and concentrated. The residue was purified using silica gel chromatography (0-5% methanol/dichloromethane) to afford the title compound (1.16 g, 4.43 mmol, 57%) as a yellow oil: 1H NMR (400 MHz, CDCl3) δ 9.22 (s, 1H), 7.36 (d, J=1.5 Hz, 1H), 6.97 (d, J=1.5 Hz, 1H), 1.48 (s, 9H); ESIMS m/z 262 ([M]+), 260 ([M−2]−).

Workup

  1. customequipped with a magnetic stir bar under a nitrogen atmosphere
  2. customthe ice bath was removed
  3. stirringThe reaction was vigorously stirred for 5 minutes
  4. customthe ice bath was removed
  5. additionAfter 5 minutes the mixture was diluted with saturated sodium bicarbonate
  6. extractionextracted with ethyl acetate
  7. washThe organics were washed with dilute sodium carbonate
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. customThe residue was purified

Sources & evidence

ORD record
ord-6bcb903c900b41b3becd72a94757d053
Source dataset
uspto-grants-2014_03
Patent number
US08680121B2

Reaction notes

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