Sodium hydride → HCID 67376843, compound

HRID 1029034Notes

Reaction equation

HRID 1029034 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6].Br[CH2:13][CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]>C1COCC1>[Br:3][C:4]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:5]=1[NH:6][CH2:13][CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 6037812-Bromo-3-methylanilineHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane

Product 1

HCID 67376843HCID 67376843, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred slurry of NaH (60% in mineral oil) (0.435 mL, 10.00 mmol) in THF (5 ml) was added dropwise a solution of 2-bromo-3-methylaniline (0.625 mL, 5 mmol) in THF (1 ml). After 15 min, (2-bromoethoxy)-tert-butyldimethylsilane (1.07 mL, 5 mmol) was added and the reaction mixture was stirred for 48 h. The reaction was quenched with water, partitioned between EtOAc and aqueous saturated ammonium chloride. The aqueous layer was extracted with EtOAc and the combined organic layers were dried over MgSO4. The solvent was removed under reduced pressure and the remaining residue was purified by flash chromatography (0-10% EtOAc/hexanes). 2-Bromo-N-(2-(tert-butyldimethylsilyloxy)ethyl)-3-methylaniline was isolated as a yellow oil.

Workup

  1. customThe reaction was quenched with water
  2. custompartitioned between EtOAc and aqueous saturated ammonium chloride
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialthe combined organic layers were dried over MgSO4
  5. customThe solvent was removed under reduced pressure
  6. customthe remaining residue was purified by flash chromatography (0-10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-cba44ffd37ed458a8194673156916e92
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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