Trimethylsilyl iodide → 1-(4-(methylthio)phenyl)-4-(piperidin-4-yloxy)pyridin-2(1H)-one

HRID 1676190Notes

Reaction equation

HRID 1676190 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]3[CH2:21][CH2:20][N:19](C(OCC4C=CC=CC=4)=O)[CH2:18][CH2:17]3)=[CH:11][C:10]2=[O:32])=[CH:5][CH:4]=1.I[Si](C)(C)C>C(Cl)Cl>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[CH:11][C:10]2=[O:32])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 67368480Benzyl 4-(1-(4-(methylthio)phenyl)-2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate

Product 1

HCID 673687081-(4-(methylthio)phenyl)-4-(piperidin-4-yloxy)pyridin-2(1H)-oneYield 73.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of benzyl 4-(1-(4-(methylthio)phenyl)-2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate (367 mg, 0.815 mmol) in CH2Cl2 (5 mL) at 0° C. was added iodotrimethylsilane (0.33 mL, 2.4 mmol, Aldrich). The reaction was stirred for 40 min and then quenched at 0° C. with HCl (1N in H2O, 5 mL). To the resulting mixture was diluted with CH2Cl2 and extracted with H2O. The H2O layer was basified with NaOH (1N in H2O, 10 mL) and extracted with CH2Cl2 (2×). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to yield 189 mg crude product as an off-white solid. MS (ESI) 317 (M+H).

Workup

  1. customquenched at 0° C. with HCl (1N in H2O, 5 mL)
  2. additionTo the resulting mixture was diluted with CH2Cl2
  3. extractionextracted with H2O
  4. extractionextracted with CH2Cl2 (2×)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-93f0dfa8277941e38782913a4fbb2972
Source dataset
uspto-grants-2011_08
Patent number
US08003796B2

Reaction notes

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