HCID 58147514, compound → 1-(6-Chloroimidazo[1,2-b]pyridazin-3-yl)-1-(6-fluoro-1-methyl-1H-indazol-5-yl)ethanol

HRID 1942051Notes

Reaction equation

HRID 1942051 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C: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:12])=[CH:9][N:10]=2)[N:7]=1.[CH3:24][Mg]Br>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C: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)([OH:12])[CH3:24])=[CH:9][N:10]=2)[N:7]=1

Participants

4

Reactant 2

HCID 58147514HCID 58147514, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 581475401-(6-Chloroimidazo[1,2-b]pyridazin-3-yl)-1-(6-fluoro-1-methyl-1H-indazol-5-yl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
38 °C

Procedure

To a stirred suspension of (6-chloro-imidazo[1,2-b]pyridazin-3-yl)-(6-fluoro-1-methyl-1H-indazol-5-yl)-methanone ((ii), 25.45 g, 74 mmol) and THF (4 L) was added methyl magnesium bromide (3 M, 43 mL) at 38° C. during 15 min. The mixture was stirred at 38° C. for 20 min. The RM was cooled to RT, quenched with 1M NaHCO3 and extracted with EtOAc (3×). The organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The title compound was obtained after crystallization in DCM-TBME (1:2) as a beige solid (tR 3.30 min (conditions 1); MH+=346).

Workup

  1. temperatureThe RM was cooled to RT
  2. customquenched with 1M NaHCO3
  3. extractionextracted with EtOAc (3×)
  4. washThe organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b7cd1ecb8e6647909c0f58a923bbaf8a
Source dataset
uspto-grants-2013_03
Patent number
US08389526B2

Reaction notes

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