Diethyl Ether → HCID 71145898, compound

HRID 535309Notes

Reaction equation

HRID 535309 reaction equation
I[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C([Mg]Br)C.C(OCC)C.[CH3:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([I:26])=[CH:22][CH:21]=1)=[O:19]>C1COCC1>[I:26][C:23]1[CH:24]=[CH:25][C:20]([C:18]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)([OH:19])[CH3:17])=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 707143-IodopyridineHCID 728691-(4-Iodophenyl)ethan-1-oneHCID 178418443HCID 178418443, compound

Product 1

HCID 71145898HCID 71145898, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-iodopyridine (0.3 g, 1.463 mmol) in THF (4 ml) was added ethylmagnesium bromide in diethylether (3M) (0.976 ml, 2.93 mmol). The mixture was stirred at room temperature overnight. GC-MS after overnight showed no starting material and the reaction mixture was cooled in an ice-bath. 4-Iodoacetophenone (0.468 g, 1.902 mmol) was added. The ice-bath was removed after 15 minutes and the reaction was stirred at room temperature for 5 hrs. The reaction mixture was quenched with aqueous saturated NH4Cl solution before dilution with ethyl acetate. The organic phase was separated and washed with brine. The organic phase was dried over Na2SO4, filtered and concentrated in vacuo to obtain the crude product which was purified by preparative HPLC (reversed phase). Fractions containing product were pooled and worked up (addition of NaHCO3, removal of acetonitrile followed by extraction with DCM) to obtain the title compound as yellowish oil.

Workup

  1. waitGC-MS after overnight showed
  2. temperatureno starting material and the reaction mixture was cooled in an ice-bath
  3. customThe ice-bath was removed after 15 minutes
  4. stirringthe reaction was stirred at room temperature for 5 hrs
  5. customThe reaction mixture was quenched with aqueous saturated NH4Cl solution before dilution with ethyl acetate
  6. customThe organic phase was separated
  7. washwashed with brine
  8. dry with materialThe organic phase was dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customto obtain the crude product which
  12. customwas purified by preparative HPLC (reversed phase)
  13. additionFractions containing product
  14. addition(addition of NaHCO3, removal of acetonitrile followed by extraction with DCM)

Sources & evidence

ORD record
ord-5f6f428aa2f6483c8e63eb96bc72bb34
Source dataset
uspto-grants-2014_10
Patent number
US08859535B2

Reaction notes

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