Pyridine → HCID 66905082, compound

HRID 1692077Notes

Reaction equation

HRID 1692077 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[C:15]([Cl:31])[C:16]=1[CH2:17][C@@H:18]1[CH2:22][CH2:21][N:20]([N:23]2[CH2:28][CH2:27][CH:26]([OH:29])[CH2:25][CH2:24]2)[C:19]1=[O:30])[O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1.N1C=CC=CC=1.[CH:38]([Si:41](OS(C(F)(F)F)(=O)=O)([CH:45]([CH3:47])[CH3:46])[CH:42]([CH3:44])[CH3:43])([CH3:40])[CH3:39]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[C:15]([Cl:31])[C:16]=1[CH2:17][C@@H:18]1[CH2:22][CH2:21][N:20]([N:23]2[CH2:28][CH2:27][CH:26]([O:29][Si:41]([CH:45]([CH3:47])[CH3:46])([CH:42]([CH3:44])[CH3:43])[CH:38]([CH3:40])[CH3:39])[CH2:25][CH2:24]2)[C:19]1=[O:30])[O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 57672065HCID 57672065, compound

Product 1

HCID 66905082HCID 66905082, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Stir a mixture of (R)-4-{3,5-dichloro-4-[1-(4-hydroxy-piperidin-1-yl)-2-oxo-pyrrolidin-3-ylmethyl]-phenoxy}-benzonitrile (0.238 g, 0.5 mmol) and 15 mL dichloromethane in an ice bath. Add pyridine (0.205 g, 2.59 mmol) followed by triisopropylsilyltrifluoromethane sulfonate (0.19 g, 0.62 mmol). Remove the cold bath and stir the reaction 1 hour at room temperature. Dilute the reaction with dichloromethane and wash with water. Dry the organic phase over sodium sulfate, filter, and concentrate. Purify the residue by silica gel chromatography by eluting with 0% to 50% ethyl acetate in hexanes gradient to afford 0.295 g of the title compound. MS (m/z): 615 (M+).

Workup

  1. customRemove the cold bath
  2. stirringstir
  3. customthe reaction 1 hour at room temperature
  4. additionDilute
  5. washwash with water
  6. dry with materialDry the organic phase over sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate
  9. customPurify the residue by silica gel chromatography
  10. washby eluting with 0% to 50% ethyl acetate in hexanes gradient

Sources & evidence

ORD record
ord-712f3dfdcafa4b878e1ba4d92abaa5f0
Source dataset
uspto-grants-2012_04
Patent number
US08153807B2

Reaction notes

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