Triphenylarsine → HCID 22177247, compound

HRID 1797168Notes

Reaction equation

HRID 1797168 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][CH2:12][N:11]([CH2:14][CH:15]([C:19]3[CH:24]=[CH:23][C:22](I)=[CH:21][CH:20]=3)[CH2:16][CH:17]=[CH2:18])[C:10]2=[O:26])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:27]([C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][CH:34]=1)#[N:28].C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F-].[Cs+]>COCCOC.C(O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][CH2:12][N:11]([CH2:14][CH:15]([C:19]3[CH:24]=[CH:23][C:22]([C:33]4[CH:32]=[CH:31][CH:30]=[C:29]([C:27]#[N:28])[CH:34]=4)=[CH:21][CH:20]=3)[CH2:16][CH:17]=[CH2:18])[C:10]2=[O:26])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

8

Reactant 4

HCID 11773TriphenylarsineHCID 25953Cesium fluorideHCID 27343253-Cyanophenylboronic acidHCID 22177242HCID 22177242, compound

Product 1

HCID 22177247HCID 22177247, compoundYield 49%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(3,5-dichloro-phenyl)-3-[2-(4-iodo-phenyl)-pent-4-enyl]-imidazolidin-2-one (0.128 g, 0.255 mmol), 3-cyanophenyl boronic acid (0.113 g, 0.766 mmol, 3 eq), tris(dibenzylidene-acetone)-dipalladium(O) (0.025g, 0.0255 mmol, 10 mol %), triphenylarsine (0.031 g, 0.1 mmol, 40 mol %) and cesium fluoride (0.075 g, 0.51 mmol, 2 eq) in DME (13 mL) and ethanol (3 mL) was microwaved at 50W for 7 h and then at 100W for 1 h. The mixture was diluted with EtOAc (50 mL), filtered through a pad of celite 545® and the filtrate washed with saturated aqueous Na2CO3 solution (25 mL). The aqueous layer was extracted twice with EtOAc (50 mL). The combined organic extracts were washed with saturated aqueous Na2CO3 solution (25 mL) and saturated aqueous sodium chloride solution (25 mL). The organic layer was separated, dried over sodium sulfate, filtered and concentrated to give a dark oil. Purification by flash column chromatography eluting 15–20% EtOAc/hexanes gave 4′-{1-[3-(3,5-dichloro-phenyl)-2-oxo-imidazolidin-1-ylmethyl]-but-3-enyl}-biphenyl-3-carbonitrile (0.059 g, 0.125 mmol, 49%) as a dark foam. 1H NMR (300 MHz, CDCl3): δ 7.98 (m, 1H), 7.92 (m, 1H), 7.74 (m, 1H), 7.64 (m, 3H), 7.58 (d, 2H), 7.45 (d, 2H), 7.11 (dd, 1H), 5.80 (m, 1H), 5.12 (m, 2H), 3.75 (m, 3H), 3.55 (m, 1H), 4.42 (m, 1H), 3.26 (m, 2H), 2.58 (dd, 2H).

Workup

  1. filtrationfiltered through a pad of celite 545®
  2. washthe filtrate washed with saturated aqueous Na2CO3 solution (25 mL)
  3. extractionThe aqueous layer was extracted twice with EtOAc (50 mL)
  4. washThe combined organic extracts were washed with saturated aqueous Na2CO3 solution (25 mL) and saturated aqueous sodium chloride solution (25 mL)
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a dark oil
  10. customPurification by flash column chromatography
  11. washeluting 15–20% EtOAc/hexanes

Sources & evidence

ORD record
ord-f42c764181544a3bab0d67544ef5d432
Source dataset
uspto-grants-2006_04
Patent number
US07034056B2

Reaction notes

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