(5,7-Difluoro-quinolin-6-yl)-[6-(1-methyl-1h-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-methanone → HCID 57917385, compound

HRID 69235Notes

Reaction equation

HRID 69235 reaction equation
[F:1][C:2]1[C:11]([C:12]([C:14]2[N:18]3[N:19]=[C:20]([C:23]4[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=4)[CH:21]=[CH:22][C:17]3=[N:16][CH:15]=2)=[O:13])=[C:10]([F:29])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH3:30][Mg]Br>C1COCC1>[F:1][C:2]1[C:11]([C:12]([C:14]2[N:18]3[N:19]=[C:20]([C:23]4[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=4)[CH:21]=[CH:22][C:17]3=[N:16][CH:15]=2)([OH:13])[CH3:30])=[C:10]([F:29])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

4

Reactant 2

HCID 68633265(5,7-Difluoro-quinolin-6-yl)-[6-(1-methyl-1h-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-methanoneHCID 178418573HCID 178418573, compound2×

Product 1

HCID 57917385HCID 57917385, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

(5,7-Difluoro-quinolin-6-yl)-[6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-methanone (Stage 191.2, 666 mg, 1.706 mmol) was dissolved in THF (13 mL) and the mixture was cooled down to 0° C. with an ice bath. A solution of methylmagnesium bromide (1.4 M, 3.05 mL) was added slowly. The RM was stirred at 0° C. for 15 min then it was warmed up to rt. After 4 h stirring, more methylmagnesium bromide (1.4 M, 1.0 mL) was added and after 1 h stirring, the reaction was quenched with a few mL of water. The RM was mixed with 10% Na2CO3 solution and the aqueous layer was extracted with EtOAc. The organics were joined and washed with brine, dried over Na2SO4 and the solvent was removed. The residue was triturated with Et2O and the yellow solid was filtered off to give the title compound (tR 1.28 min (conditions 12), MH+=407).

Workup

  1. temperatureit was warmed up to rt
  2. stirringAfter 4 h stirring
  3. stirringstirring
  4. customthe reaction was quenched with a few mL of water
  5. additionThe RM was mixed with 10% Na2CO3 solution
  6. extractionthe aqueous layer was extracted with EtOAc
  7. washwashed with brine
  8. dry with materialdried over Na2SO4
  9. customthe solvent was removed
  10. customThe residue was triturated with Et2O
  11. filtrationthe yellow solid was filtered off

Sources & evidence

ORD record
ord-31a52289202d47c1a723e3081adc214d
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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