Hydrochloric Acid → N-(4-benzyl-2-iodophenyl)-2-fluoro-4-formylbenzamide

HRID 2075245Notes

Reaction equation

HRID 2075245 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([CH:11]=[O:12])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].C(N(C(C)C)C(C)C)C.[CH2:22]([C:29]1[CH:34]=[CH:33][C:32]([NH2:35])=[C:31]([I:36])[CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Cl>C1COCC1.CCOCC>[CH2:22]([C:29]1[CH:34]=[CH:33][C:32]([NH:35][C:4](=[O:5])[C:3]2[CH:7]=[CH:8][C:9]([CH:11]=[O:12])=[CH:10][C:2]=2[F:1])=[C:31]([I:36])[CH:30]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 584152862-Fluoro-4-formylbenzoyl chlorideHCID 584153354-Benzyl-2-iodobenzenamine

Product 1

HCID 59651840N-(4-benzyl-2-iodophenyl)-2-fluoro-4-formylbenzamide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a slurry of 2-fluoro-4-formylbenzoyl chloride (1.5 mmol) in 5 mL THF was added N-ethyl-N-isopropylpropan-2-amine (0.39 mL, 2.2 mmol) and 4-benzyl-2-iodobenzenamine (0.41 g, 1.3 mmol). After 30 min, the reaction was treated with 1N HCl and Et2O. The organic layer was washed 1×1N HCl, 2×sat'd aq. NaHCO3, and 1× brine. The org. layer was dried over MgSO4, filtered, and concentrated in vacuo. The resulting material was purified by ISCO, 40 g, 0-20% EtOAc/hexanes to give N-(4-benzyl-2-iodophenyl)-2-fluoro-4-formylbenzamide as a white solid. MS (ESI) m/z: Calculated: 459.0; Observed: 457.9 (M−−1).

Workup

  1. washThe organic layer was washed 1×1N HCl, 2×
  2. dry with materiallayer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting material was purified by ISCO, 40 g, 0-20% EtOAc/hexanes

Sources & evidence

ORD record
ord-81115906bdf24d3eb25394cf22d26e2a
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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