2-(Tributylstannyl)pyridine → HCID 24984109, compound

HRID 1710400Notes

Reaction equation

HRID 1710400 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][N:6]1[CH2:10][C:9]2([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[O:8][C:7]1=[O:16].C([Sn](CCCC)(CCCC)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1)CCC>C1(C)C=CC=CC=1>[N:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][N:6]1[CH2:10][C:9]2([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[O:8][C:7]1=[O:16]

Participants

4

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 57559811HCID 57559811, compound

Product 1

HCID 24984109HCID 24984109, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

3-(3-Iodo-benzyl)-1-oxa-3-aza-spiro[4.5]decan-2-one (0.148 mmol, 55 mg), 2-tributylstannanyl-pyridine (0.222 mmol, 81.72 mg), tetrakispalladium(0) (0.03 mmol, 34.2 mg) were combined and dissolved in toluene (5 mL). The reaction mixture was left to stir at 110° C. overnight. It was then filtered through silica and the filtrate was concentrated in vacuo. The residue was purified by SPE flash column chromatography using silica gel and ethyl/acetate/hexanes (0˜50%) as eluent. The product was impure by NMR. Therefore, it was dissolved in dichloromethane, and 2M hydrogen chloride in diethyl ether (10 mL) was added. This solution was concentrated in vacuo, the residue was dissolved in water (10 mL) and washed with hexanes. The aqueous layer was then neutralized using sodium bicarbonate and washed with dichloromethane. The organic layer was concentrated in vacuo to give the final product was a pale yellow gum (10 meg, 21%). 1H NMR (300 MHz, CDCl3): δ (ppm)=8.71 (m, 1H), 7.92 (m, 2H), 7.77 (m, 2H), 7.49 (m, 1H), 7.37 (m, 1H), 7.27 (m, 1H), 4.53 (s, 2H), 3.14 (s, 2H), 1.78 (m, 4H), 1.51 (m, 6H).

Workup

  1. waitThe reaction mixture was left
  2. filtrationIt was then filtered through silica
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by SPE flash column chromatography
  5. dissolutionTherefore, it was dissolved in dichloromethane
  6. addition2M hydrogen chloride in diethyl ether (10 mL) was added
  7. concentrationThis solution was concentrated in vacuo
  8. dissolutionthe residue was dissolved in water (10 mL)
  9. washwashed with hexanes
  10. washwashed with dichloromethane
  11. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-0fcb1ce834024b7fb5ab0b909dacd8a9
Source dataset
uspto-grants-2010_09
Patent number
US07790717B2

Reaction notes

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