(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-(3-methyl-3h-benzoimidazol-5-yl)-methanone → (Rac)-1-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-1-(3-methyl-3h-benzoimidazol-5-yl)-ethanol

HRID 69231Notes

Reaction equation

HRID 69231 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([C:13]3[CH:22]=[CH:21][C:16]4[N:17]=[CH:18][N:19]([CH3:20])[C:15]=4[CH:14]=3)=[O:12])=[CH:9][N:10]=2)[N:7]=1.[CH3:23][Mg]Br>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([C:13]3[CH:22]=[CH:21][C:16]4[N:17]=[CH:18][N:19]([CH3:20])[C:15]=4[CH:14]=3)([OH:12])[CH3:23])=[CH:9][N:10]=2)[N:7]=1

Participants

5

Reactant 2

HCID 87524396(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-(3-methyl-3h-benzoimidazol-5-yl)-methanoneHCID 178418573HCID 178418573, compound2×

Product 1

HCID 87523187(Rac)-1-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-1-(3-methyl-3h-benzoimidazol-5-yl)-ethanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-(3-methyl-3H-benzoimidazol-5-yl)-methanone (Stage 185.4, 560 mg, 1.796 mmol) was dissolved in THF (50 mL) with heating under Argon. The solution was let to cool down and methylmagnesium bromide (3 M, 0.719 mL) was added. The mixture was stirred at rt for 1 h. To complete the reaction, more methylmagnesium bromide (3 M, 0.30 mL) was added and the RM was stirred 30 min longer. It was then diluted with EtOAc and washed with a saturated NaHCO3 sol. The aqueous phase was extracted twice with EtOAc. The combined organics were washed with brine, dried over Na2SO4, filtered and evaporated. The residue was dried under vacuum overnight to afford the title compound as an off white foam (tR 1.84 min (conditions 8), MH+=328).

Workup

  1. temperaturewith heating under Argon
  2. temperatureto cool down
  3. additionwas added
  4. stirringthe RM was stirred 30 min longer
  5. washwashed with a saturated NaHCO3 sol. The aqueous phase
  6. extractionwas extracted twice with EtOAc
  7. washThe combined organics were washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was dried under vacuum overnight

Sources & evidence

ORD record
ord-0d6650be3f394e6dbef901e7a7c5a623
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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