Iodine → HCID 86700480, compound

HRID 1404838Notes

Reaction equation

HRID 1404838 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([NH2:11])[C:3]=1[N+:12]([O-:14])=[O:13].[F:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH2:21])=[CH:18][CH:17]=1.C(N(CC)CC)C.II>C(OCC)(=O)C.CN(C=O)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:21][CH2:20][C:19]2[CH:22]=[CH:23][C:16]([F:15])=[CH:17][CH:18]=2)=[C:3]([N+:12]([O-:14])=[O:13])[C:4]=1[NH2:11])([O-:10])=[O:9]

Participants

7

Reactant 4

HCID 807IodineHCID 8471TriethylamineHCID 673264-FluorobenzylamineHCID 86700481HCID 86700481, compound

Product 1

HCID 86700480HCID 86700480, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A round bottom flask is charged with 8 (2.01 g, 10 mmol, 1 equiv), 4-fluorobenzylamine (3.79 g, 30 mmol, 3 equiv) and triethylamine (1.21 g, 12 mmol, 1.2 equiv). DMF (40 mL) is then added to the above mixture followed by iodine (catalytic, 1 mg). The reaction mixture is then heated to 120° C. and stirred at 120° C. for 16 hrs after which the flask is allowed to cool to room temperature. The reaction mixture is diluted with ethyl acetate and washed with water (5×80 mL) and dried with brine and then over MgSO4. The suspension is filtered and concentrated to give a residue, which is purified by silica gel flash chromatography (hexanes/ethyl acetate) to give the desired product (9).

Workup

  1. temperatureto cool to room temperature
  2. washwashed with water (5×80 mL)
  3. dry with materialdried with brine
  4. filtrationThe suspension is filtered
  5. concentrationconcentrated
  6. customto give a residue, which
  7. customis purified by silica gel flash chromatography (hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-f735f8952e614bf992af7192605f64a5
Source dataset
uspto-grants-2014_12
Patent number
US08916133B2

Reaction notes

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