Bromoacetonitrile → HCID 86715536, compound

HRID 2284627Notes

Reaction equation

HRID 2284627 reaction equation
[Br:1][C:2]1[N:7]=[N:6][C:5](/[N:8]=[CH:9]/N(C)C)=[CH:4][CH:3]=1.Br[CH2:14][C:15]#[N:16].C([O-])(O)=O.[Na+]>CC(O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:14]([C:15]#[N:16])=[CH:9][N:8]=2)[N:7]=1

Participants

6

Reactant 3

HCID 11534BromoacetonitrileHCID 516892Sodium BicarbonateHCID 178484240HCID 178484240, compound

Product 1

HCID 86715536HCID 86715536, compoundYield 53.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

(E)-N′-(6-Bromopyridazin-3-yl)-N,N-dimethylformimidamide (2.5 g, 10.9 mmol), bromoacetonitrile (3.92 g, 32.7 mmol) and NaHCO3 (1.8 g, 21.8 mmol) in i-PrOH (15 mL) were heated at 75° C. for 8 h while stirring the contents. Subsequently, the dark reaction mixture was diluted with water and the resulting solid was collected by filtration. The solid was purified by flash chromatography (Combiflash® companion System® with RediSep® silica gel column 40 g and 15-30-50% EtOAC/hexanes as an eluting solvent) to obtain 1.3 g of 6-bromoimidazo[1,2-b]pyridazine-3-carbonitrile. 1H NMR (300 MHz, DMSO-d6) δ 8.58 (s, 1H), 8.33 (d, J=9.5 Hz, 1H), 7.77 (d, J=9.5 Hz, 1H).

Workup

  1. customSubsequently, the dark reaction mixture
  2. filtrationthe resulting solid was collected by filtration
  3. customThe solid was purified by flash chromatography (Combiflash® companion System® with RediSep® silica gel column 40 g and 15-30-50% EtOAC/hexanes as an eluting solvent)

Sources & evidence

ORD record
ord-87e7f633f8ad421e9418254f49f4d91b
Source dataset
uspto-grants-2015_09
Patent number
US09145433B2

Reaction notes

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