HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Iodine chloride → 3-Iodo-8-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine

HRID 269021
Notes
Print preview

Reaction equation

HRID 269021 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[C:4]2[N:5]([CH:19]=[CH:20][N:21]=2)[CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[CH:8]=1.C([O-])(=O)C.[Na+].[I:29]Cl>C(O)(=O)C>[I:29][C:19]1[N:5]2[CH:6]=[C:7]([C:9]3[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=3)[CH:8]=[C:3]([C:2]([F:1])([F:22])[F:23])[C:4]2=[N:21][CH:20]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24640Iodine chlorideHCID 517045Sodium AcetateHCID 866080098-Trifluoromethyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine

Product 1

HCID 866080083-Iodo-8-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridineYield 72.7%

Reagents, catalysts & solvents 1

HCID 176Acetic Acid
Solvent

Conditions

Temperature
23 °C

Procedure

To a solution of 8-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine (1.36 g, 4.1 mmol) in 5 mL of acetic acid was added sodium acetate (0.51 g, 6.2 mmol) and a solution of iodine monochloride (2 M, 2.5 mL, 5.0 mmol)- slightly exothermic. The reaction mixture was stirred for 30 min at 23° C., precipitate formed, then partitioned between 60 mL of water and 60 mL of EtOAc. The organic layer was washed with sat. NaHCO3, water, aq. sodium thiosulfate, water, then dried over Na2SO4, filtered and concentrated to give 1.36 g (72%) of an off-white solid. MS (ISP) 457.3 [(M+H)+].

Workup

  1. customprecipitate formed
  2. custompartitioned between 60 mL of water and 60 mL of EtOAc
  3. washThe organic layer was washed with sat. NaHCO3, water, aq. sodium thiosulfate, water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d76b45e4fb3d48548fa507538b022c71
Source dataset
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07446113B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes