N-Iodosuccinimide → HCID 86640503, compound

HRID 340769Notes

Reaction equation

HRID 340769 reaction equation
C1C(=O)N([I:8])C(=O)C1.[C:9]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:14]=[CH:13][C:12]([CH2:15][NH:16][C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[C:18]=2[N+:25]([O-:27])=[O:26])=[CH:11][CH:10]=1>CC(O)=O>[C:9]1([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:10]=[CH:11][C:12]([CH2:15][NH:16][C:17]2[CH:22]=[C:21]([F:23])[C:20]([I:8])=[C:19]([F:24])[C:18]=2[N+:25]([O-:27])=[O:26])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 67361471HCID 67361471, compound

Product 1

HCID 86640503HCID 86640503, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

NIS (7.9 g, 35.1 mmol) was added to a solution of N-(biphenyl-4-ylmethyl)-3,5-difluoro-2-nitroaniline (10.86 g, 31.9 mmol) in AcOH (150 mL). After heating at 70° C. for 2 h, the reaction mixture was concentrated and partitioned between EtOAc and saturated aqueous NaHCO3. The organic phase was separated, washed with brine, dried (Na2SO3) and concentrated. The resulting solid was recrystallized from DCM/hexanes afforded the desired product as a red solid.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. custompartitioned between EtOAc and saturated aqueous NaHCO3
  3. customThe organic phase was separated
  4. washwashed with brine
  5. dry with materialdried (Na2SO3)
  6. concentrationconcentrated
  7. customThe resulting solid was recrystallized from DCM/hexanes

Sources & evidence

ORD record
ord-8c9558ffeeae44a8a654ddb4e6209732
Source dataset
uspto-grants-2014_11
Patent number
US08895596B2

Reaction notes

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