Benzyl Alcohol → HCID 86665019, compound

HRID 1051758Notes

Reaction equation

HRID 1051758 reaction equation
[C:1]1([CH2:7][OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[C:12]1[C:13]2[N:14]([CH:19]=[CH:20][N:21]=2)[N:15]=[C:16]([Cl:18])[CH:17]=1.O>C1COCC1>[CH2:7]([O:8][C:12]1[C:13]2[N:14]([CH:19]=[CH:20][N:21]=2)[N:15]=[C:16]([Cl:18])[CH:17]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 24758Sodium hydrideHCID 468352698-Bromo-6-chloroimidazo(1,2-b)pyridazine

Product 1

HCID 86665019HCID 86665019, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of phenylmethanol (3.35 g, 31 mmol, 1.2 eq) in THF (80 mL), NaH (60% dispersion in mineral oil, 1.34 g, 33.5 mmol, 1.3 eq) is added in portions. The resulting mixture is stirred at RT for 30 min and then 8-bromo-6-chloroimidazo[1,2-b]pyridazine (D-3) (6 g, 25.8 mmol, 1.0 eq) is added. The resulting mixture is stirred at RT for an additional 2 h and then poured into water (30 mL). The mixture is extracted with ethyl acetate (2×100 mL). The combined organic layers are washed with brine, dried over Na2SO4 and filtered. The filtrate is concentrated in vacuo to afford the product, 8-(benzyloxy)-6-chloroimidazo[1,2-b]pyridazine (D-4).

Workup

  1. stirringThe resulting mixture is stirred at RT for an additional 2 h
  2. extractionThe mixture is extracted with ethyl acetate (2×100 mL)
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-2cf0b8277a6244cd98ca38cb8d1116c1
Source dataset
uspto-grants-2016_07
Patent number
US09388183B2

Reaction notes

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