Sodium borohydride → (6-Chloro-2-cyclopropylimidazo[1,2-b]pyridazin-3-yl)methanol

HRID 1896409Notes

Reaction equation

HRID 1896409 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[N:8]([C:10]([CH:16]=[O:17])=[C:11]([CH:13]3[CH2:15][CH2:14]3)[N:12]=2)[N:9]=1>CO>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[N:8]([C:10]([CH2:16][OH:17])=[C:11]([CH:13]3[CH2:14][CH2:15]3)[N:12]=2)[N:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 577430506-Chloro-2-cyclopropylimidazo[1,2-b]pyridazine-3-carbaldehyde

Product 1

HCID 58009731(6-Chloro-2-cyclopropylimidazo[1,2-b]pyridazin-3-yl)methanolYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (5.62 mg, 6.62 mmol, 1.3 eq) is added dropwised, at room temperature, to a solution of 6-chloro-2-cyclopropylimidazo[1,2-b]pyridazine-3-carbaldehyde x110 (958 mg, 4.32 mmol) in methanol (100 ml). After 1 hour, the reaction is quenched by water (100 ml) and the crude product is extracted by dichloromethane (2×100 ml). The organic layers are dried over MgSO4, filtered and condensed under reduced pressure to afford (6-chloro-2-cyclopropylimidazo[1,2-b]pyridazin-3-yl)methanol x115 which is used without any further purification.

Workup

  1. customthe reaction is quenched by water (100 ml)
  2. extractionthe crude product is extracted by dichloromethane (2×100 ml)
  3. dry with materialThe organic layers are dried over MgSO4
  4. filtrationfiltered
  5. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-79537ae1afab49f1a0aa40aa28ae613f
Source dataset
uspto-grants-2013_08
Patent number
US08518943B2

Reaction notes

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