Pyridine → 3-{1-[Bis(4-chlorophenyl)methyl]azetidin-3-ylidene}-3-(3,5-difluorophenyl)propanenitrile

HRID 1724183Notes

Reaction equation

HRID 1724183 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[N:9]2[CH2:12][C:11](=[C:13]([C:16]3[CH:21]=[C:20]([F:22])[CH:19]=[C:18]([F:23])[CH:17]=3)[CH2:14]O)[CH2:10]2)=[CH:4][CH:3]=1.CS(OS(C)(=O)=O)(=O)=O.[C-]#N.[Na+].[N:43]1C=CC=C[CH:44]=1>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[N:9]2[CH2:12][C:11](=[C:13]([C:16]3[CH:21]=[C:20]([F:22])[CH:19]=[C:18]([F:23])[CH:17]=3)[CH2:14][C:44]#[N:43])[CH2:10]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8929Sodium CyanideHCID 81560Methanesulfonic anhydrideHCID 113742342-{1-[Bis(4-chlorophenyl)methyl]azetidin-3-ylidene}-2-(3,5-difluorophenyl)ethanol

Product 1

HCID 670659213-{1-[Bis(4-chlorophenyl)methyl]azetidin-3-ylidene}-3-(3,5-difluorophenyl)propanenitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The reaction mixture of 51 mg (0.114 mmol) of 2-{1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene}-2-(3,5-difluorophenyl)ethanol, 24 mg (0.137 mmol) of methanesulfonic anhydride, 14 mg (0.285 mmol) of sodium cyanide and 11 uL (0.137 mmol) pyridine in 5 mL of acetonitrile was stirred for 12 h at rt, and then concentrated. The residue was purified by silica gel chromatography with hexanes/ethyl acetate to the title compound; 1NMR(CDCl3) δ 3.29 (s, 2H), 3.96 (s, 2H), 4.01 (s, 2H), 4.54 (s, 1H), 6.69-6.75 (m, 3H), 7.29-6-7.7.38 (m, 8H); Mass Spectrum: m/e=455 (M+1 35Cl, 35Cl) and 457 (M+1 35Cl, 37Cl).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by silica gel chromatography with hexanes/ethyl acetate to the title compound

Sources & evidence

ORD record
ord-0d6e6028ca7a4170bda862a420a76f89
Source dataset
uspto-grants-2009_02
Patent number
US07485732B2

Reaction notes

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