Sodium borohydride → (4-Chloro-2-fluorophenyl)(6-chloro-2-methyl-8-(morpholinomethyl)imidazo[1,2-b]pyridazin-3-yl)methanol

HRID 597860Notes

Reaction equation

HRID 597860 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[N:14]3[N:15]=[C:16]([Cl:26])[CH:17]=[C:18]([CH2:19][N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)[C:13]3=[N:12][C:11]=2[CH3:27])=[O:9])=[C:4]([F:28])[CH:3]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[N:14]3[N:15]=[C:16]([Cl:26])[CH:17]=[C:18]([CH2:19][N:20]4[CH2:21][CH2:22][O:23][CH2:24][CH2:25]4)[C:13]3=[N:12][C:11]=2[CH3:27])[OH:9])=[C:4]([F:28])[CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 56954584(4-Chloro-2-fluorophenyl)(6-chloro-2-methyl-8-(morpholinomethyl)imidazo[1,2-b]pyridazin-3-yl)methanone

Product 1

HCID 86642488(4-Chloro-2-fluorophenyl)(6-chloro-2-methyl-8-(morpholinomethyl)imidazo[1,2-b]pyridazin-3-yl)methanolYield 94.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Combine (4-chloro-2-fluorophenyl)(6-chloro-2-methyl-8-(morpholinomethyl)imidazo[1,2-b]pyridazin-3-yl)methanone (0.43 g, 1.0 mmol) and methanol (15 mL) in a round bottom flask. Place under nitrogen and cool to 0° C. Add sodium borohydride (58 mg, 1.5 equiv.) in one portion. Stir for 5 min at this temperature then remove cooling bath and let warm to RT. After 15 min, quench the reaction with water then extract with EA. Wash the organics with water followed by aqueous saturated sodium chloride. Dry the organics over anhydrous magnesium sulfate. Filter and concentrate in vacuo to give the title compound (0.4 g, 93%). LCMS (4 min)=425.0, 427.0, M+1.

Workup

  1. customthen remove
  2. temperaturecooling bath
  3. temperaturelet warm to RT
  4. waitAfter 15 min
  5. customquench
  6. customthe reaction with water
  7. extractionthen extract with EA
  8. washWash the organics with water
  9. dry with materialDry the organics over anhydrous magnesium sulfate
  10. filtrationFilter
  11. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-11ea8772602c4cbba81c070ebd78be75
Source dataset
uspto-grants-2011_03
Patent number
US07897600B2

Reaction notes

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