Sodium Hydroxide → HCID 18771514, compound

HRID 1417082Notes

Reaction equation

HRID 1417082 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 2.5N 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-9fd60e1f89d6499388c5e6d39bb218fe
Source dataset
uspto-grants-1999_06
Patent number
US05916891

Reaction notes

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