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

HRID 1842409Notes

Reaction equation

HRID 1842409 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-3f547ab65c9f4668831ffdcccdf51312
Source dataset
uspto-grants-2015_02
Patent number
US08946222B2

Reaction notes

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