Selectfluor → 8-Bromo-6-chloro-3-fluoroimidazo[1,2-b]pyridazine

HRID 2239863Notes

Reaction equation

HRID 2239863 reaction equation
Cl.[Br:2][C:3]1[C:4]2[N:5]([CH:10]=[CH:11][N:12]=2)[N:6]=[C:7]([Cl:9])[CH:8]=1.[B-](F)(F)(F)[F:14].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>CC#N>[Br:2][C:3]1[C:4]2[N:5]([C:10]([F:14])=[CH:11][N:12]=2)[N:6]=[C:7]([Cl:9])[CH:8]=1

Participants

4

Reactant 2

HCID 2724933SelectfluorHCID 714638758-Bromo-6-chloroimidazo[1,2-b]pyridazine hydrochloride

Product 1

HCID 866117428-Bromo-6-chloro-3-fluoroimidazo[1,2-b]pyridazineYield 24.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a 20 ml reaction vial was added 8-bromo-6-chloroimidazo[1,2-b]pyridazine hydrochloride salt (0.33 g, 1.4 mmol) from Example I(1), step 1b, CH3CN (7.0 ml) and selectflor (0.5 g, 1.4 mmol). The reaction was stirred at 50 C for 6 hrs, then concentrated to dryness. Purification was done by silica gel chromatography (ethyl acetate/heptane, 25 min gradient: 5-50% ethyl acetate) to give 0.085 g of 8-bromo-6-chloro-3-fluoroimidazo[1,2-b]pyridazine.

Workup

  1. customIn a 20 ml reaction
  2. concentrationconcentrated to dryness
  3. customPurification
  4. customwas done by silica gel chromatography (ethyl acetate/heptane, 25 min gradient: 5-50% ethyl acetate)

Sources & evidence

ORD record
ord-6468b58c199946da9f9e6135062aa72e
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

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