Diethyl Ether → HCID 22872664, compound

HRID 365861Notes

Reaction equation

HRID 365861 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([O:10][CH2:11][C@@H:12]2[CH2:15][CH2:14][N:13]2C(OC(C)(C)C)=O)[CH:6]=[N:7][C:8]=1[Cl:9])#N.[C:23]1([Mg]Br)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CC[O:33]CC>>[ClH:9].[C:1]([C:3]1[CH:4]=[C:5]([O:10][CH2:11][C@@H:12]2[CH2:15][CH2:14][NH:13]2)[CH:6]=[N:7][C:8]=1[Cl:9])(=[O:33])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 3

HCID 3283Diethyl Ether2×HCID 22872671HCID 22872671, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 22872664HCID 22872664, compound

Procedure

The 5-cyano-6-chloro-3-(1-BOC-2-(S)-azetidinylmethoxy)pyridine of example 92a in anhydrous Et2O at 0° C. is treated with 1.5 equivalents of phenylmagnesium bromide in Et2O and stirring is maintained at 0 to 35° C. until the nitrile is largely consumed. The solvent is evaporated and the residue is treated with 2M aqueous potassium hydrogen sulfate to hydrolyze the intermediate imine. The solution is made basic with potassium carbonate and extracted with EtOAc. The combined extracts are dried (Na2SO4) and concentrated to a residue which is chromatographed (silica gel) to afford the title compound.

Workup

  1. customis largely consumed
  2. customThe solvent is evaporated
  3. additionthe residue is treated with 2M aqueous potassium hydrogen sulfate
  4. extractionextracted with EtOAc
  5. dry with materialThe combined extracts are dried (Na2SO4)
  6. concentrationconcentrated to a residue which
  7. customis chromatographed (silica gel)

Sources & evidence

ORD record
ord-1f7694cf013542558486a93cffb25985
Source dataset
uspto-grants-2000_10
Patent number
US06127386

Reaction notes

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