Ethanol → HCID 71227653, compound

HRID 1483859Notes

Reaction equation

HRID 1483859 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][N:9]=[CH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)=[N:6][CH:7]=1.CCO.C(OI(C1C=CC=CC=1)OC(=O)C)(=O)C>C(Cl)Cl>[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:18])[F:19])[CH:12]=3)=[N:9][N:8]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 76724Iodobenzene diacetateHCID 71227627HCID 71227627, compound

Product 1

HCID 71227653HCID 71227653, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-iodo-2-(2-(3-(trifluoromethyl)benzylidene)hydrazinyl)pyridine (1.60 g, 4.09 mmol) in DCM (10 mL)/EtOH (1 mL), was added PhI(OAc)2 (1.845 g, 5.73 mmol). The mixture was stirred at RT for 5 h, then the solvent was removed in vacuo. The residue was dissolved in DCM and purified on SiO2 column chromatography with 80% 15% MeOH/EA in hexane to afford the title compound (1.21 g, 76% yield) as an off-white solid. MS (ES+, m/z): 390.3 (M++1).

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in DCM
  3. custompurified on SiO2 column chromatography with 80% 15% MeOH/EA in hexane

Sources & evidence

ORD record
ord-4bb3ddad931b4a5cb2eba3ec02873f88
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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