8-Iodo-3-(phenylsulfonyl)quinoline → Tert-butyl 3-(3-(phenylsulfonyl)quinolin-8-yl)azetidine-1-carboxylate

HRID 884342Notes

Reaction equation

HRID 884342 reaction equation
I[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:14])=[O:13])=[CH:7]2.[I-].[C:22]([O:26][C:27]([N:29]1[CH2:32][CH:31]([Zn+])[CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23]>CC(N(C)C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].[Cu]I>[C:15]1([S:12]([C:8]2[CH:9]=[N:10][C:11]3[C:6]([CH:7]=2)=[CH:5][CH:4]=[CH:3][C:2]=3[CH:31]2[CH2:30][N:29]([C:27]([O:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:28])[CH2:32]2)(=[O:14])=[O:13])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 2

HCID 114067748-Iodo-3-(phenylsulfonyl)quinolineHCID 178452187HCID 178452187, compound

Product 1

HCID 66854416Tert-butyl 3-(3-(phenylsulfonyl)quinolin-8-yl)azetidine-1-carboxylateYield 25%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 31374DimethylacetamideSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of 8-iodo-3-(phenylsulfonyl)quinoline (200 mg, 0.51 mmol, prepared according to WO2003080580) in DMA (1 ml) was added PdCl2(dppf) (8.3 mg, 0.10 mmol; dppf=1,1′-bis(diphenylphosphino)ferrocene) and CuI (11.6 mg, 0.06 mmol), followed by dropwise addition of (1-(tert-butoxycarbonyl)azetidin-3-yl)-zinc(II) iodide (317 mg, 0.91 mmol) in DMA (1 ml) over 10 min. The mixture was then heated at 80° C. for 6 h, then stirred at room temperature for 150 h and quenched with a saturated aqueous solution of NaCl. The reaction mixture was extracted with tert.-butyl-methyl-ether (MTBE). The organic phases were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography to give the title compound (54 mg, 25%) as a light yellow oil.

Workup

  1. customquenched with a saturated aqueous solution of NaCl
  2. extractionThe reaction mixture was extracted with tert.-butyl-methyl-ether (MTBE)
  3. dry with materialThe organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-73cc6bda9ea94c439ed8379b9c2996c3
Source dataset
uspto-grants-2012_08
Patent number
US08242102B2

Reaction notes

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