Pyridine → Methyl {1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene}(3,5-difluorophenyl)acetate

HRID 1724169Notes

Reaction equation

HRID 1724169 reaction equation
[CH3:1][O:2][C:3](=[O:33])[CH:4]([C:13]1(O)[CH2:16][N:15]([CH:17]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[CH2:14]1)[C:5]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]([F:12])[CH:6]=1.N1C=CC=CC=1.N1(C2CCCCCCCCCC2)CCCCCCCCCN1>ClCCl>[Cl:31][C:28]1[CH:27]=[CH:26][C:25]([CH:17]([C:18]2[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=2)[N:15]2[CH2:14][C:13](=[C:4]([C:5]3[CH:6]=[C:7]([F:12])[CH:8]=[C:9]([F:11])[CH:10]=3)[C:3]([O:2][CH3:1])=[O:33])[CH2:16]2)=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 57346892DiazabicycloundecaneHCID 67055297Methyl{1-[bis(4-chlorophenyl)methyl]-3-hydroxyazetidin-3-yl}(3,5-difluorophenyl)acetate

Product 1

HCID 57559907Methyl {1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene}(3,5-difluorophenyl)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.71 g (1.44 mmol) of methyl{1-[bis(4-chlorophenyl)methyl]-3-hydroxyazetidin-3-yl}(3,5-difluorophenyl)acetate, 0.295 g (1.73 mmol) of methanesulfonyl anhydride, and 0.400 mL pyridine in 5 mL of dichloromethane was stirred at room temperature overnight. To this was added 0.400 mL of diazabicycloundecane and the solution remained stirring at room temperature. The mixture was partitioned between ether and water and the aqueous layer was washed with 20 mL of ether. The organic layers were washed with brine, combined, dried over MgSO4 and concentrated. The residue was filtered through a pad of silica gel using 20% ether-hexane to afford the title compound; 1NMR(CDCl3) δ 3.67 (s, 3H), 3.84 (m, 2H), 4.25 (m, 2H), 4.54 (s, 1H), 6.76 (m, 1H), 6.78 (m, 2H), 7.33 (m, 4H), 7.38 (m, 4H); Mass Spectrum: m/e=474 (M+1 35Cl, 35Cl) and 476 (M+1 35Cl, 37Cl).

Workup

  1. customThe mixture was partitioned between ether and water
  2. washthe aqueous layer was washed with 20 mL of ether
  3. washThe organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. filtrationThe residue was filtered through a pad of silica gel using 20% ether-hexane

Sources & evidence

ORD record
ord-92b480fbf58b430db00143e48bc9b00d
Source dataset
uspto-grants-2009_02
Patent number
US07485732B2

Reaction notes

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