Ammonium Chloride → HCID 71272254, compound

HRID 475236Notes

Reaction equation

HRID 475236 reaction equation
CON(C)[C:4]([C:6]1[CH:20]=[CH:19][C:9]2[N:10]([CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][O:14]3)[CH:11]=[N:12][C:8]=2[CH:7]=1)=[O:5].[CH3:22][CH2:23][Mg+].[Br-].[NH4+].[Cl-]>C1COCC1>[O:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH:13]1[N:10]1[C:9]2[CH:19]=[CH:20][C:6]([C:4](=[O:5])[CH2:22][CH3:23])=[CH:7][C:8]=2[N:12]=[CH:11]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 86694687HCID 86694687, compoundHCID 178461630HCID 178461630, compound

Product 1

HCID 71272254HCID 71272254, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To the solution of 168 (70 mg, 0.24 mmol) and THF cooled to 0° C. under Ar was added EtMgBr (0.72 mL, 1M solution). The mixture was stirred at 0° C. for 2 h then NH4Cl solution was added carefully. The mixture was extracted with EtOAc, washed sequentially with H2O and brine and dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography to afford 45 mg (72%) of 1-[1-(tetrahydro-pyran-2-yl)-1H-benzoimidazol-5-yl]-propan-1-one (170) as a colorless oil.

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washwashed sequentially with H2O and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by SiO2 chromatography

Sources & evidence

ORD record
ord-b85143f4b8a74dadbbca250753cee811
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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