Imidazole → HCID 71285448, compound

HRID 1481725Notes

Reaction equation

HRID 1481725 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:11][CH2:12][C:13](=[O:14])[C:6]3=[CH:5][C:4]=2[CH:3]=1.[BH4-].[Na+].[CH3:17][C:18]([Si:21](Cl)([CH3:23])[CH3:22])([CH3:20])[CH3:19].N1C=CN=C1>CO.O>[Br:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:11][CH2:12][CH:13]([O:14][Si:21]([C:18]([CH3:20])([CH3:19])[CH3:17])([CH3:23])[CH3:22])[C:6]3=[CH:5][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 4311764Sodium borohydrideHCID 58221535HCID 58221535, compound

Product 1

HCID 71285448HCID 71285448, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 7-bromo-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-one (1.1 g, 4.4 mmol) in MeOH (20 mL), cooled to 0° C., was added NaBH4 (0.33 g, 8.8 mmol). After stirring at 0° C. for 1 h, the reaction was quenched with H2O and then extracted with CH2Cl2. The combined organic phases were dried over Na2SO4, filtered, and concentrated to afford a white solid which was used without further purification. The crude solid was dissolved in CH2Cl2 (20 mL) and TBSCl (0.7 g, 4.4 mmol) and imidazole (0.33 g, 4.4 mmol) were added. After stirring at room temperature for 1 h, the reaction mixture was poured into H2O and extracted with CH2Cl2. The combined organic phases were dried over Na2SO4, filtered, and concentrated to afford the title compound as a white solid (1.26 g, 79%).

Workup

  1. customthe reaction was quenched with H2O
  2. extractionextracted with CH2Cl2
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford a white solid which
  7. customwas used without further purification
  8. dissolutionThe crude solid was dissolved in CH2Cl2 (20 mL)
  9. stirringAfter stirring at room temperature for 1 h
  10. extractionextracted with CH2Cl2
  11. dry with materialThe combined organic phases were dried over Na2SO4
  12. filtrationfiltered
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-8cef41101cce4fdf8ef63f6a1205f24f
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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