Diethyl Ether → HCID 22872628, compound

HRID 2305144Notes

Reaction equation

HRID 2305144 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>>[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 22872628HCID 22872628, 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-8ec2a42ddfbd45d1911ac02df6ad16aa
Source dataset
uspto-grants-2002_08
Patent number
US06437138B1

Reaction notes

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