1,4-Dioxane → HCID 178466043, compound

HRID 413239Notes

Reaction equation

HRID 413239 reaction equation
I[C:2]1[CH:25]=[CH:24][C:5]2[NH:6][C:7]([N:9]3[CH2:14][CH2:13][C:12]4([C:22]5[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=5)[C:16](=[O:23])[O:15]4)[CH2:11][CH2:10]3)=[N:8][C:4]=2[CH:3]=1.[O:26]1CCO[CH2:28][CH2:27]1>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:27]([C:2]1[CH:25]=[CH:24][C:5]2[NH:6][C:7]([N:9]3[CH2:14][CH2:13][C:12]4([C:22]5[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=5)[C:16](=[O:23])[O:15]4)[CH2:11][CH2:10]3)=[N:8][C:4]=2[CH:3]=1)(=[O:26])[CH3:28]

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 1785190321'-(5-iodo-1H-benzimidazol-2-yl)spiro[isobenzofuran-1,4'-piperidin]-3-one

Product 1

HCID 178466043HCID 178466043, compound

Reagents, catalysts & solvents 1

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalyst

Procedure

Add 1-ethoxyvinyltri-N-butyltin (0.49 g, 1.35 mmol) and bis (triphenyl-phosphine) palladium (II) chloride (0.05 g) to a solution of 1′-(5-iodo-1H-benzimidazol-2-yl)-spiro[isobenzofuran-1,4′-piperidin]-3-one (0.12 g, 0.27 mmol) in dioxane (5 mL). Reflux the reaction mixture for 12 hours. After cooling to ambient temperature, concentrate the reaction mixture in vacuo, and add to a solution of 10% HCl (2 mL) in THF (5 mL). After stirring for 30 minutes, dilute the solution with EtOAc (30 mL), and wash with saturated NaHCO3 (30 mL) and saturated aqueous NaCl (30 mL). Dry the organic portion over Na2SO4, filter and concentrate. Purify by preparative TLC (10% MeOH—CH2Cl2) to obtain 1′-(5-acetyl-1H-benzimidazol-2-yl)-spiro[isobenzofuran-1,4′-piperidin]-3-one as a yellow solid.

Workup

  1. temperatureReflux the reaction mixture for 12 hours
  2. concentrationconcentrate the reaction mixture in vacuo
  3. additionadd to a solution of 10% HCl (2 mL) in THF (5 mL)
  4. additiondilute the solution with EtOAc (30 mL)
  5. washwash with saturated NaHCO3 (30 mL) and saturated aqueous NaCl (30 mL)
  6. dry with materialDry the organic portion over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate
  9. customPurify by preparative TLC (10% MeOH—CH2Cl2)

Sources & evidence

ORD record
ord-d5e31e1f80b3423fb4ace95e9f2eb8b8
Source dataset
uspto-grants-2003_05
Patent number
US06566367B2

Reaction notes

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