Sodium Hydroxide → 6-Chloro-3-((6-fluoro-1-methyl-1H-indazol-5-yl)methyl)imidazo[1,2-b]pyridazine

HRID 69285Notes

Reaction equation

HRID 69285 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:11]([C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][C:21]=3[F:22])[N:18]([CH3:23])[N:17]=[CH:16]4)O)=[CH:9][N:10]=2)[N:7]=1.[I-].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[CH:14]=[C:15]4[C:19](=[CH:20][C:21]=3[F:22])[N:18]([CH3:23])[N:17]=[CH:16]4)=[CH:9][N:10]=2)[N:7]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 30165Iodide IonHCID 4124402Phosphinic AcidHCID 58147531(6-chloroimidazo[1,2-b]pyridazin-3-yl)(6-fluoro-1-methyl-1H-indazol-5-yl)methanol

Product 1

HCID 581906096-Chloro-3-((6-fluoro-1-methyl-1H-indazol-5-yl)methyl)imidazo[1,2-b]pyridazine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(rac)-(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-(6-fluoro-1-methyl-1H-indazol-5-yl)-methanol (Stage 278.4, 1 g, 3.01 mmol) was dissolved in acetic acid (80 mL) and introduced in 4 microwave reactors. Iodide (956 mg×4, 15.07 mmol), followed by H3PO2 50% (1.2 m×4, 45.2 mmol) were then added into each reactor. Then they were submitted to microwave irradiations 5 min at 150° C. After combination, 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. The residue was triturated with Et2O to afford the title compound (tR 1.26 min (conditions 2), MH+=316)

Workup

  1. additionintroduced in 4 microwave reactors
  2. additionwere then added into each reactor
  3. customirradiations 5 min
  4. customat 150° C
  5. extractionextracted twice with EtOAc
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. customthe solvent was removed
  9. customThe residue was triturated with Et2O

Sources & evidence

ORD record
ord-f95561dc4ab84e8e9be628eb3538e30f
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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