Sodium Hydroxide → HCID 18771514, compound

HRID 1387630Notes

Reaction equation

HRID 1387630 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[N:12]=2)=[CH:4][CH:3]=1.[I:26]Cl.[OH-].[Na+]>C(O)(=O)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)=[C:11]([C:13]3[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=3)[N:12]=2)=[CH:4][C:3]=1[I:26]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24640Iodine chlorideHCID 99020414-[4-(4-Fluorophenyl)-5-(4-pyridinyl)-1H-imidazol-2-yl]benzenamine

Product 1

HCID 18771514HCID 18771514, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 2-(4-aminophenyl)-4-(4-fluorophenyl)-5-(4-pyridyl)-1H-imidazole (50 mg, 0.15 mmol) [See Ex. 28 above] in glacial acetic acid (5 mL) was added a solution of ICl (24 mg, 0.15 mmol) in glacial acetic acid (1.5 mL). The resulting mixture was stirred at rt for 1 h, then poured into saturated aqueous Na2S2O5. The pH was adjusted to neutral by the addition of 2.5 N NaOH and extracted with EtOAc. The organic extract was concentrated under reduced pressure, and the residue was purified by flash chroma-tography, eluting with a solvent gradient of 2-10% MeOH/CHCl3. The material that was isolated was recrystallized from Et2O/Hex to afford the title compound: 1H NMR (CDCl3): d 8.42 (d, 2H); 8.18 (d, 1H); 7.68 (dd, 2H); 7.42 (m, 4H); 7.09 (t, 2H); 6.77 (d, 1H).

Workup

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. concentrationwas concentrated under reduced pressure
  4. customthe residue was purified by flash chroma-tography
  5. washeluting with a solvent gradient of 2-10% MeOH/CHCl3
  6. customThe material that was isolated
  7. customwas recrystallized from Et2O/Hex

Sources & evidence

ORD record
ord-70bfb88e31534b14bf2e3c2932117d5b
Source dataset
uspto-grants-2001_07
Patent number
US06268370B1

Reaction notes

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