Water → (Rac)-1-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-1-quinolin-6-yl-ethanol

HRID 69197Notes

Reaction equation

HRID 69197 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:20](=[CH:21][CH:22]=3)[N:19]=[CH:18][CH:17]=[CH:16]4)=[O:12])=[CH:9][N:10]=2)[N:7]=1.[CH3:23][Mg]Br.O>C1COCC1.C1(C)C=CC=CC=1.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:20](=[CH:21][CH:22]=3)[N:19]=[CH:18][CH:17]=[CH:16]4)([OH:12])[CH3:23])=[CH:9][N:10]=2)[N:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 86630275(6-Chloroimidazo[1,2-b]pyridazin-3-yl)(quinolin-6-yl)methanoneHCID 178418573HCID 178418573, compound

Product 1

HCID 87523391(Rac)-1-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-1-quinolin-6-yl-ethanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22635083Tetrahydrofuran tolueneSolvent

Conditions

Temperature
0 °C

Procedure

(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-quinolin-6-yl-methanone (Stage 1.2, 500 mg, 1.62 mmol) was dissolved in anhydrous THF (10 mL) and cooled down to 0° C. Methylmagnesium bromide in toluene/THF (1.4 M, 1.27 mL) was slowly added and the RM was then warmed up to rt and stirred for 4 h. Water (2 mL) was added and the precipitate formed was filtered off. The filtrate was concentrated to give the title compound as a brown solid (tR 0.50 min (conditions 2), (MH+=325).

Workup

  1. temperaturethe RM was then warmed up to rt
  2. customthe precipitate formed
  3. filtrationwas filtered off
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-689ce011c6a8432fa57aec440e4fb6a6
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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