Iodine → HCID 57917275, compound

HRID 69290Notes

Reaction equation

HRID 69290 reaction equation
II.O[PH2]=O.[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[N:11]([C:13]([C:16]([C:19]3[CH:20]=[CH:21][C:22]4[N:23]([CH:25]=[CH:26][N:27]=4)[CH:24]=3)(O)[CH3:17])=[CH:14][N:15]=2)[N:12]=1.[OH-].[Na+]>C(O)(=O)C>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[N:11]([C:13]([CH:16]([C:19]3[CH:20]=[CH:21][C:22]4[N:23]([CH:25]=[CH:26][N:27]=4)[CH:24]=3)[CH3:17])=[CH:14][N:15]=2)[N:12]=1

Participants

6

Reactant 4

HCID 807IodineHCID 14798Sodium HydroxideHCID 4124402Phosphinic AcidHCID 87523871(Rac)-1-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-1-(imidazo[1,2-a]pyridin-6-yl)ethanol

Product 1

HCID 57917275HCID 57917275, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
150 °C

Procedure

Iodine (4.8 g, 18.91 mmol) and H3PO2 (5.1 mL of a 50% aqueous solution, 46.8 mmol) were added to a solution of (rac)-1-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-1-(imidazo[1,2-a]pyridin-6-yl)ethanol (Stage 292.1, 1.85 g, 5.90 mmol) in acetic acid (50 mL). The RM was portion wise in 3 different microwave reactors and was heated at 150° C. for 5 min under microwave irradiations. It was basified with 2.5 N NaOH solution and then it was extracted twice with EtOAc/MeOH (9:1) twice. Combined organic layers was washed with brine and dried over Na2SO4, filtered and concentrated to give the title compound as a brown solid (tR 0.5 min (conditions 2), MH+=298)

Workup

  1. extractionit was extracted twice with EtOAc/MeOH (9:1) twice
  2. washCombined organic layers was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d015060e79b54a65b317e2272ad33c27
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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