Iodine → 6-(6-Chloro-imidazo[1,2-b]pyridazin-3-ylmethyl)-5,7-difluoro-quinoline

HRID 69211Notes

Reaction equation

HRID 69211 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:11]([C:13]3[C:14]([F:24])=[C:15]4[C:20](=[CH:21][C:22]=3[F:23])[N:19]=[CH:18][CH:17]=[CH:16]4)O)=[CH:9][N:10]=2)[N:7]=1.II.O[PH2]=O.[OH-].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:11][C:13]3[C:14]([F:24])=[C:15]4[C:20](=[CH:21][C:22]=3[F:23])[N:19]=[CH:18][CH:17]=[CH:16]4)=[CH:9][N:10]=2)[N:7]=1

Participants

6

Reactant 4

HCID 807IodineHCID 14798Sodium HydroxideHCID 4124402Phosphinic AcidHCID 58147519(6-Chloroimidazo[1,2-b]pyridazin-3-yl)(5,7-difluoroquinolin-6-yl)methanol

Product 1

HCID 581475266-(6-Chloro-imidazo[1,2-b]pyridazin-3-ylmethyl)-5,7-difluoro-quinoline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
150 °C

Procedure

(rac)-(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-(5,7-difluoro-quinolin-6-yl)-methanol (Stage 171.3, 200 mg, 0.577 mmol) was dissolved in acetic acid (4.93 mL) and introduced in a microwave reactor together with iodine (439 mg, 1.731 mmol) and H3PO2 (0.47 mL of a 50% aqueous solution, 8.65 mmol). The RM was stirred under microwave irradiations at 150° C. for 5 min. It was basified by a 2.5 M NaOH solution and extracted twice with EtOAc. The organics were joined and washed with brine, dried over Na2SO4 and the solvent was removed to afford the title compound as a beige solid (tR 1.0 min (conditions 2), MH+=331).

Workup

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

Sources & evidence

ORD record
ord-8cfbceb23df54e64a4e32a33904b46a3
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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