Water → HCID 66630216, compound

HRID 1411433Notes

Reaction equation

HRID 1411433 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-157cee9c9e4d4c1d817084dfc12ce94b
Source dataset
uspto-grants-2014_12
Patent number
US08921514B2

Reaction notes

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