Imidazole → (S)-4-Bromo-1-(tert-butyl-dimethyl-silanyloxy)-indan-5-carbonitrile

HRID 625703Notes

Reaction equation

HRID 625703 reaction equation
[Br:1][C:2]1[C:10]([C:11]#[N:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C@@H:6]2[OH:13].N1C=CN=C1.[C:19]([Si:23]([CH3:26])([CH3:25])Cl)([CH3:22])([CH3:21])[CH3:20]>CN(C)C=O.O>[Br:1][C:2]1[C:10]([C:11]#[N:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C@@H:6]2[O:13][Si:23]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:26])[CH3:25]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 86700772(S)-4-bromo-1-hydroxy-indan-5-carbonitrile

Product 1

HCID 123266554(S)-4-Bromo-1-(tert-butyl-dimethyl-silanyloxy)-indan-5-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(S)-4-Bromo-1-hydroxy-indan-5-carbonitrile (0.90 g, 3.78 mmol), imidazole (0.64 g, 9.45 mmol) and tert-butyldimethylchlorosilane (0.80 g, 5.29 mmol) are suspended in dry N,N-dimethylformamide and stirred at room temperature for 3 hours. The mixture is diluted with water and extracted with ethyl acetate. The organic extracts are dried and the solvent removed to give the crude product which is used directly in the next step (Yield 1.20 g).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic extracts are dried
  3. customthe solvent removed

Sources & evidence

ORD record
ord-387363667b5943e4a343ac8bb203ef8a
Source dataset
uspto-grants-2016_04
Patent number
US09308194B2

Reaction notes

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