Water → (6-Chloroimidazo[1,2-b]pyridazin-3-yl)(quinolin-6-yl)methanol

HRID 69149Notes

Reaction equation

HRID 69149 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[N:8]([C:10]([C:13]([C:15]3[CH:16]=[C:17]4[C:22](=[CH:23][CH:24]=3)[N:21]=[CH:20][CH:19]=[CH:18]4)=[O:14])=[CH:11][N:12]=2)[N:9]=1.O>C(O)C>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[N:8]([C:10]([CH:13]([C:15]3[CH:16]=[C:17]4[C:22](=[CH:23][CH:24]=3)[N:21]=[CH:20][CH:19]=[CH:18]4)[OH:14])=[CH:11][N:12]=2)[N:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86630275(6-Chloroimidazo[1,2-b]pyridazin-3-yl)(quinolin-6-yl)methanone

Product 1

HCID 87524298(6-Chloroimidazo[1,2-b]pyridazin-3-yl)(quinolin-6-yl)methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (103 mg, 2.62 mmol) was added to a solution of (6-chloro-imidazo[1,2-b]pyridazin-3-yl)-quinolin-6-yl-methanone (Stage 1.2, 1.62 g, 5.25 mmol) in ethanol (17 mL) and the solution was stirred at rt for 4 h. Water was then added and the mixture extracted with 9:1 DCM/MeOH. The organic extracts were dried, filtered and concentrated to afford the title compound as a brown solid (tR 1.0 min (conditions 1), MH+=311).

Workup

  1. extractionthe mixture extracted with 9:1 DCM/MeOH
  2. customThe organic extracts were dried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fd5fab9b4216470b9370b797af4c469c
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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