Iodine → HCID 59333310, compound

HRID 1893484Notes

Reaction equation

HRID 1893484 reaction equation
[B-](F)(F)(F)F.[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1.[I:22]I.[F:24][C:25]([F:51])([F:50])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[C:32]1[CH:33]=[C:34]2[C:39](=[CH:40][CH:41]=1)[N:38]1[CH:42]=[CH:43][N:44]=[C:37]1[C:36]([NH:45][CH2:46][CH2:47][CH2:48][OH:49])=[N:35]2>C(#N)C>[I:22][C:42]1[N:38]2[C:39]3[C:34]([N:35]=[C:36]([NH:45][CH2:46][CH2:47][CH2:48][OH:49])[C:37]2=[N:44][CH:43]=1)=[CH:33][C:32]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[C:25]([F:24])([F:50])[F:51])=[CH:41][CH:40]=3

Participants

5

Reactant 3

HCID 807IodineHCID 2724933SelectfluorHCID 59333343HCID 59333343, compound

Product 1

HCID 59333310HCID 59333310, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture protected from light of Selectfluor (103 mg; 0.29 mmol; 1.4 eq) and iodine (63 mg; 0.248 mmol; 1.2 eq) in acetonitrile (1.8 ml) stirred for 10 min under argon is added 3-({7-[2-(trifluoromethyl)phenyl]imidazo[1,2-a]quinoxalin-4-yl}amino) propan-1-ol (80 mg; 0.207 mmol; 1 eq) prepared as in example 5. The reaction mixture is stirred at rt overnight. Filtration of solid side-products, concentration, dissolution in ethyl acetate, washing with brine, aqueous sodium carbonate and water, drying (magnesium sulphate) and purification by prep CCM on silicagel (dichloromethane/methanol 95:5) affords the title product as an orange oil (88 mg; 0.17 mmol; 82%).

Workup

  1. additionis added
  2. stirringThe reaction mixture is stirred at rt overnight
  3. filtrationFiltration of solid side-products, concentration, dissolution in ethyl acetate
  4. washwashing with brine, aqueous sodium carbonate and water
  5. customdrying
  6. custom(magnesium sulphate) and purification by prep CCM on silicagel (dichloromethane/methanol 95:5)

Sources & evidence

ORD record
ord-fba513836efd4713941ca595ce9d0680
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

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