Iodine → (Rac)-6-[1-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-ethyl]-5,7-difluoro-quinoline

HRID 69224Notes

Reaction equation

HRID 69224 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([C:14]3[C:15]([F:25])=[C:16]4[C:21](=[CH:22][C:23]=3[F:24])[N:20]=[CH:19][CH:18]=[CH:17]4)(O)[CH3:12])=[CH:9][N:10]=2)[N:7]=1.II.O[PH2]=O.[OH-].[Na+]>O.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:11]([C:14]3[C:15]([F:25])=[C:16]4[C:21](=[CH:22][C:23]=3[F:24])[N:20]=[CH:19][CH:18]=[CH:17]4)[CH3:12])=[CH:9][N:10]=2)[N:7]=1

Participants

7

Reactant 4

HCID 807IodineHCID 14798Sodium HydroxideHCID 4124402Phosphinic AcidHCID 58147518(Rac)-1-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-1-(5,7-difluoro-quinolin-6-yl)-ethanol

Product 1

HCID 58147541(Rac)-6-[1-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-ethyl]-5,7-difluoro-quinoline

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

(rac)-1-(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-1-(5,7-difluoro-quinolin-6-yl)-ethanol (Stage 182.2, 570 mg, 1.58 mmol), iodine (1.203 g, 4.74 mmol) and H3PO2 (1.293 mL of a 50% aqueous solution, 23.7 mmol) were charged together with acetic acid (16 mL) in a microwave vial. The mixture was subjected to MW-irradiation at 150° C. for 5 min. It was then taken up with water and basified with NaOH (2.5 M). It was extracted with EtOAc twice and the organics were joined and washed with brine, dried over Na2SO4 and the solvent was removed. The title compound was obtained as a yellow solid (tR 1.1 min (conditions 2), MH+=346).

Workup

  1. extractionIt was extracted with EtOAc twice
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customthe solvent was removed

Sources & evidence

ORD record
ord-915221ec81dd4525a1e8fc4d858b9fae
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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