Lead diacetate → HCID 57487856, compound

HRID 1160207Notes

Reaction equation

HRID 1160207 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[O:12][C:11](=[O:13])[N:10]([CH2:14][C:15]3[CH:20]=[CH:19][C:18](I)=[CH:17][CH:16]=3)[CH2:9]2)=[CH:4][CH:3]=1.C([O-])(=O)C.[Pb+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+].[N:62]1[CH:67]=[CH:66][CH:65]=[CH:64][C:63]=1[CH:68]1[CH2:73][NH:72][CH2:71][CH2:70][N:69]1[CH3:74]>C1(C)C=CC=CC=1.ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[O:12][C:11](=[O:13])[N:10]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([N:72]4[CH2:71][CH2:70][N:69]([CH2:68][C:63]5[CH:64]=[CH:65][CH:66]=[CH:67][N:62]=5)[CH2:74][CH2:73]4)=[CH:17][CH:16]=3)[CH2:9]2)=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 9317Lead diacetateHCID 10796Cesium carbonateHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 24968759HCID 24968759, compoundHCID 53802796HCID 53802796, compound

Product 1

HCID 57487856HCID 57487856, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 5-(R)-(4-Chloro-phenyl)-3-(4-Iodo-benzyl)-oxazolidin-2-one (50 mg, 0.12 mmol), lead acetate (3 mg, 0.012 mmol), 2-(dicyclohexyl phosphino) biphenyl (5 mg, 0.014 mmol) and cesium carbonate (118 mg, 0.36 mmol) in toluene (2.5 mL), was added 2-pyridyl methyl piperazine and the reaction flask was heated at 100° C. for 3 h. The reaction mixture was diluted with dichloromethane (6 mL), washed with water (3 mL), brine (3 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by chromatography on silica gel, eluting with dichloromethane containing 0.5-2% ammonia (2 M) in methanol The title compound was isolated as an off white solid (30 mg, 54%). 1H NMR (300 MHz, CDCl3): δ 8.6 (m, 1H), 7.69 (m, 1H), 7.44 (d, 1H), 7.35 (m, 2H), 7.25 (m, 5H), 6.88 (m, 2H), 5.42 (t, 1H), 4.45 (d, 1H), 4.33 (d, 1H), 3.75 (m, 3H), 3.24 (m, 5H), 2.69 (m, 4H).

Workup

  1. washwashed with water (3 mL), brine (3 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography on silica gel
  5. washeluting with dichloromethane containing 0.5-2% ammonia (2 M) in methanol The title compound

Sources & evidence

ORD record
ord-066997456c3a4057ac5f6a6451f5c76f
Source dataset
uspto-grants-2010_10
Patent number
US07816354B2

Reaction notes

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