Water → HCID 66630216, compound

HRID 1053897Notes

Reaction equation

HRID 1053897 reaction equation
[Br:1][C:2]1[C:3]([F:23])=[CH:4][C:5]2[N:9]=[C:8]([C@@H:10]3[CH2:14][CH2:13][CH2:12][N:11]3[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[NH:7][C:6]=2[CH:22]=1.[H-].[Na+].[CH3:26][Si:27]([CH3:34])([CH3:33])[CH2:28][CH2:29][O:30][CH2:31]Cl.O>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[C:3]([F:23])=[CH:4][C:5]2[N:9]([CH2:31][O:30][CH2:29][CH2:28][Si:27]([CH3:34])([CH3:33])[CH3:26])[C:8]([C@@H:10]3[CH2:14][CH2:13][CH2:12][N:11]3[C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])=[N:7][C:6]=2[CH:22]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178451902HCID 178451902, compound

Product 1

HCID 66630216HCID 66630216, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-tert-butyl 2-(6-bromo-5-fluoro-1H-benzo[d]imidazol-2-yl)pyrrolidine-1-carboxylate (2.5 g, 6.4 mol) in THF (32 mL) was added sodium hydride (0.27 g, 6.8 mmol) and stirring was continued for 30 minutes. 2-(Trimethylsilyl)-ethoxymethyl chloride (1.2 mL, 6.8 mmol) was added and stirring was continued for 30 minutes. Water was added to quench the reaction. The mixture was diluted with EtOAc, washed with 1N HCl, H2O, and brine, dried (Na2SO4), filtered and concentrated to an oil. The oil was purified by flash chromatography (0-30% EtOAc/hexane) to give the title compound (2.9 g, 5.7 mmol, 89%).

Workup

  1. stirringstirring
  2. waitwas continued for 30 minutes
  3. customto quench
  4. customthe reaction
  5. washwashed with 1N HCl, H2O, and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated to an oil
  9. customThe oil was purified by flash chromatography (0-30% EtOAc/hexane)

Sources & evidence

ORD record
ord-9f0a78291068460ba1ca480a3a0350cb
Source dataset
uspto-grants-2016_07
Patent number
US09394279B2

Reaction notes

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