8-Iodo-3-(phenylsulfonyl)quinoline → HCID 44474551, compound

HRID 2068131Notes

Reaction equation

HRID 2068131 reaction equation
CC(C)([O-])C.[Na+].[N:7]1([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:11]2[CH2:12][NH:13][CH2:14][CH:10]2[CH2:9][CH2:8]1.I[C:23]1[CH:24]=[CH:25][CH:26]=[C:27]2[C:32]=1[N:31]=[CH:30][C:29]([S:33]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)(=[O:35])=[O:34])=[CH:28]2>O1CCOCC1.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:36]1([S:33]([C:29]2[CH:30]=[N:31][C:32]3[C:27]([CH:28]=2)=[CH:26][CH:25]=[CH:24][C:23]=3[N:13]2[CH2:14][CH:10]3[CH2:9][CH2:8][N:7]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:11]3[CH2:12]2)(=[O:35])=[O:34])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

7

Reactant 3

HCID 114067748-Iodo-3-(phenylsulfonyl)quinolineHCID 23676156Sodium t-butoxideHCID 44474550tert-butyl hexahydropyrrolo[3,4-b]pyrrole-1(2H)-carboxylate

Product 1

HCID 44474551HCID 44474551, compoundYield 38%

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
40 °C

Procedure

A solution of sodium t-butoxide (70 mg, 0.71 mmol) and tert-butyl hexahydropyrrolo-[2,3-c]pyrrole-1(2H)-carboxylate (537 mg, 2.53 mmol) in dioxane (3 mL) was stirred under nitrogen. To this was added 1,1′-bis(diphenylphosphino)ferrocene (25 mg, 0.05 mmol), Pd2(DBA)3 (12 mg, 0.02 mmol) and 8-iodo-3-(phenylsulfonyl)quinoline (200 mg, 0.51 mmol), followed by the addition of a further 2 mL of dioxane. The mixture was then heated at 40° C. for 12 h before partitioning between CH2Cl2 and water. The mixture was filtered through Celite and the organic phase was separated. The water phase was extracted twice with CH2Cl2 and the combined extracts dried (Na2SO4), filtered and concentrated in vacuo to provide the crude material, which was purified by flash chromatography to give the title compound (92 mg, 38%) as a light yellow oil.

Workup

  1. custombefore partitioning between CH2Cl2 and water
  2. filtrationThe mixture was filtered through Celite
  3. customthe organic phase was separated
  4. extractionThe water phase was extracted twice with CH2Cl2
  5. dry with materialthe combined extracts dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto provide the crude material, which
  9. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-ad566244061f431aa162ad43c0ed6e9f
Source dataset
uspto-grants-2012_10
Patent number
US08293913B2

Reaction notes

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