Phenol → 1'-pentyl-6-phenoxyspiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

HRID 545960Notes

Reaction equation

HRID 545960 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]2[C:8]3([CH2:23][O:24][C:4]=2[CH:3]=1)[C:16]1[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=1)[N:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:9]3=[O:22].Cl.CN(C)CC(O)=O.C(=O)([O-])[O-].[Cs+].[Cs+].[C:39]1([OH:45])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>O1CCOCC1.ClCCl.[Cu](I)I>[CH2:17]([N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]2([C:5]3[CH:6]=[CH:7][C:2]([O:45][C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)=[CH:3][C:4]=3[O:24][CH2:23]2)[C:9]1=[O:22])[CH2:18][CH2:19][CH2:20][CH3:21]

Participants

8

Reactant 4

HCID 996PhenolHCID 10796Cesium carbonateHCID 75605N,N-Dimethylglycine hydrochlorideHCID 592634366-bromo-1'-pentylspiro[1-benzofuran-3,3'-indol]-2'(1'H)one

Product 1

HCID 592633841'-pentyl-6-phenoxyspiro[1-benzofuran-3,3'-indol]-2'(1'H)-oneYield 92.2%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 6-bromo-1′-pentylspiro[1-benzofuran-3,3′-indol]-2′(1′H)-one (0.08 g, 0.19 mmol) in anhydrous dioxane (4.00 mL) was added copper iodide (0.01 g, 0.01 mmol), N,N-dimethyl glycine hydrochloride (0.01 g, 0.01 mmol), cesium carbonate (0.17 g, 0.52 mmol) and phenol (0.03 g, 0.32 mmol). The resulted mixture was refluxed for 16 h under nitrogen, diluted with dichloromethane (50.0 mL) and filtered through a celite bed. The filtrate was concentrated in vacuo to dryness. The residue was subjected to column chromatography (ethyl acetate/hexane, 1/6) to give the title compound (0.07 g, 87%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 7.36-7.28 (m, 3H), 7.20-7.00 (m, 4H), 6.92 (d, 1H), 6.62 (dd, 1H), 6.58 (br, 1H), 6.44 (dd, 1H), 4.95 (d, 1H), 4.71 (d, 1H), 3.92-3.64 (m, 2H), 1.70-1.68 (m, 2H), 1.43-1.34 (m, 4H), 0.92 (t, 3H); MS (ES+) m/z 400.5 (M+1).

Workup

  1. temperatureThe resulted mixture was refluxed for 16 h under nitrogen
  2. filtrationfiltered through a celite bed
  3. concentrationThe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-bda5749bc1e342589cd312c4738cb80b
Source dataset
uspto-grants-2011_05
Patent number
US07935721B2

Reaction notes

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