Sodium Iodide → HCID 70874844, compound

HRID 2172182Notes

Reaction equation

HRID 2172182 reaction equation
[Cl:1][C:2]1[N:3]([CH2:10][CH2:11][C@@H:12]([OH:25])[CH2:13][O:14]S(C2C=CC(C)=CC=2)(=O)=O)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[CH3:26][N:27]([CH2:39][CH2:40][CH:41]1[CH2:46][CH2:45][N:44]([C:47]2[CH:52]=[CH:51][C:50](O)=[CH:49][CH:48]=2)[CH2:43][CH2:42]1)[C:28]1[CH:33]=[CH:32][C:31]([O:34][C:35]([F:38])([F:37])[F:36])=[CH:30][CH:29]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[I-].[Na+]>C(O)C.C(OCC)(=O)C>[Cl:1][C:2]1[N:3]([CH2:10][CH2:11][C@@H:12]([OH:25])[CH2:13][O:14][C:50]2[CH:49]=[CH:48][C:47]([N:44]3[CH2:45][CH2:46][CH:41]([CH2:40][CH2:39][N:27]([CH3:26])[C:28]4[CH:29]=[CH:30][C:31]([O:34][C:35]([F:38])([F:36])[F:37])=[CH:32][CH:33]=4)[CH2:42][CH2:43]3)=[CH:52][CH:51]=2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 62657Potassium Phosphate, TribasicHCID 70873338HCID 70873338, compoundHCID 86709368HCID 86709368, compound

Product 1

HCID 70874844HCID 70874844, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Toluene-4-sulfonic acid (R)-4-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxybutyl ester (988 mg) and 4-(4-{2-[N-methyl-N-(4-trifluoromethoxyphenyl)amino]ethyl}piperidin-1-yl)phenol (1.0 g) were suspended in ethanol (30 ml). Tripotassium phosphate (1.08 g) and sodium iodide (418 mg) were added to the suspension, and the mixture was stirred at 80° C. under a nitrogen atmosphere for 4.5 hours. After being cooled to room temperature, ethyl acetate (20 ml) was added to the reaction mixture, insoluble matter was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1→methylene chloride:methanol=97:3) to afford the title compound as a reddish brown oil (1.17 g).

Workup

  1. temperatureAfter being cooled to room temperature
  2. customwas removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1→methylene chloride:methanol=97:3)

Sources & evidence

ORD record
ord-d7055b55971440fcb167daeab21aa4e3
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

Loading…