Sodium borohydride → Imidazo[1,2-b]pyridazin-6-ylmethanol

HRID 1798695Notes

Reaction equation

HRID 1798695 reaction equation
[BH4-].[Na+].[N:3]1[CH:4]=[CH:5][N:6]2[C:11]=1[CH:10]=[CH:9][C:8]([C:12](OC)=[O:13])=[N:7]2>C1COCC1.CO>[N:3]1[CH:4]=[CH:5][N:6]2[C:11]=1[CH:10]=[CH:9][C:8]([CH2:12][OH:13])=[N:7]2

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 59580147Methyl imidazo[1,2-b]pyridazine-6-carboxylate

Product 1

HCID 59580099Imidazo[1,2-b]pyridazin-6-ylmethanolYield 81%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (1.1 g, 31.1 mmol) was added to a solution of methyl imidazo[1,2-b]pyridazine-6-carboxylate (2.4 g, 15.5 mmol) in THF (35 mL) and methanol (2.5 ml) at RT. The reaction mixture was stirred at RT for 2 h (the reaction was monitored by TLC) upon which the mixture was concentrated under reduced pressure. The reaction mixture was diluted with water and extracted with EtOAc. The combined organics were dried over sodium sulfate, filtered and concentrated under reduced pressure to afford imidazo[1,2-b]pyridazin-6-ylmethanol (1.6 g, 81%) as a white solid. 1H NMR: 200 MHz, DMSO-d6: δ 8.5 (s, 1H), 8.3 (d, 1H), 7.9 (s, 1H), 7.55 (d, 1H), 5.65 (t, 1H), 4.6 (d, 2H). MS: [M+H]+: m/z=311.2.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. additionThe reaction mixture was diluted with water
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d06906ab5095437fb6719884caa7309a
Source dataset
uspto-grants-2013_01
Patent number
US08343973B2

Reaction notes

Loading…