Iodoethane → HCID 86694743, compound

HRID 475259Notes

Reaction equation

HRID 475259 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:11]2[CH:12]=[CH:13][C:14]([CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:15][C:10]=2[N:9]=[CH:8]1.[H-].[Na+].I[CH2:28][CH3:29]>CN(C=O)C>[CH2:28]([N:17]([CH2:16][C:14]1[CH:13]=[CH:12][C:11]2[N:7]([CH:2]3[CH2:3][CH2:4][CH2:5][CH2:6][O:1]3)[CH:8]=[N:9][C:10]=2[CH:15]=1)[C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:23])[CH3:22])[CH3:29]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 86694742HCID 86694742, compound

Product 1

HCID 86694743HCID 86694743, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 202 (600 mg, 1.81 mmol) in DMF (4.5 mL) at 0° C. was added NaH (101 mg, 2.54 mmol, 60% in oil). The reaction was warmed to RT and stirred for 25 min, then re-cooled to 0° C. and iodoethane (0.27 mL, 3.26 mmol) was added. The reaction was warmed to RT and stirred for 5 h. The reaction mixture was partitioned between EtOAc and H2O. The EtOAc extract was washed thrice with water, dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by SiO2 chromatography to afford 360 mg (55%) of tert-butyl ethyl((1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)methyl)carbamate (208): MS (ESI) m/z=360.3 [M+1]+

Workup

  1. temperaturere-cooled to 0° C.
  2. temperatureThe reaction was warmed to RT
  3. stirringstirred for 5 h
  4. customThe reaction mixture was partitioned between EtOAc and H2O
  5. extractionThe EtOAc extract
  6. washwas washed thrice with water
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude residue was purified by SiO2 chromatography

Sources & evidence

ORD record
ord-b24ba5972f5f4f07be2e1340c84f11d5
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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