Sodium borohydride → (6-Chloroimidazo(1,2-b)pyridazin-3-yl)methanol

HRID 870733Notes

Reaction equation

HRID 870733 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:11]=[O:12])=[CH:9][N:10]=2)[N:7]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:11][OH:12])=[CH:9][N:10]=2)[N:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 114467026-Chloroimidazo[1,2-b]pyridazine-3-carbaldehyde

Product 1

HCID 57352521(6-Chloroimidazo(1,2-b)pyridazin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-chloroimidazo[1,2-b]pyridazine-3-carbaldehyde (0.55 g, 3 mmol) in methanol (20 mL) was added sodium borohydride (0.15 g, 4 mmol) in a small portions at rt. After stirring at rt for 30 min, the reaction was quenched with water, and extracted with DCM to give crude product (0.55 g, 100% yield). 40 mg of crude product was purified by Prep HPLC to give (6-chloroimidazo[1,2-b]pyridazin-3-yl)methanol as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.95 (d, J=9.35 Hz, 1H), 7.79 (s, 1H), 7.11 (d, J=9.35 Hz, 1H), 5.07 (s, 2H); LRMS (ESI) m/e 184.0 [(M+H)+, calcd for C7H7ClN3O 184.6].

Workup

  1. customthe reaction was quenched with water
  2. extractionextracted with DCM
  3. customto give crude product (0.55 g, 100% yield)
  4. custom40 mg of crude product was purified by Prep HPLC

Sources & evidence

ORD record
ord-4e134c146a2c424e818bd9193469f1f9
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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