Potassium Hydroxide → HCID 67265143, compound

HRID 1685148Notes

Reaction equation

HRID 1685148 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[NH:15][CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=3)[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:28][CH2:29][O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32].[OH-].[K+]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:15]([CH2:28][CH2:29][O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=3)[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 178451794HCID 178451794, compound

Product 1

HCID 67265143HCID 67265143, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Combine 4-[4-(3,4-difluoro-phenyl)-1H-imidazol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (10.0 g; 0.028 mol; 1.0 equiv), (2-bromo-ethoxy)-tert-butyl-dimethyl-silane (13.16 g; 0.055 mol; 2.0 equiv), powdered KOH (7.72 g; 0.14 mol; 5.0 equiv) in THF (100 mL) and stir at 40° C. for 16 h. Quench the reaction with water and extract with EA. Evaporate to give the title compound (14.3 g, crude). MS (ES+): m/z=522 (M+H)

Workup

  1. customQuench
  2. customthe reaction with water
  3. extractionextract with EA
  4. customEvaporate

Sources & evidence

ORD record
ord-67fe10e9876449abb8c0e3d88ab5adf3
Source dataset
uspto-grants-2012_04
Patent number
US08148387B2

Reaction notes

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