Ammonium formate → HCID 67466567, compound

HRID 2284371Notes

Reaction equation

HRID 2284371 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=1.C([O-])=O.[NH4+]>CCO.[OH-].[OH-].[Pd+2]>[N:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:4]2[C:5]3[N:6]([CH:8]=[CH:9][N:10]=3)[N:7]=[CH:2][CH:3]=2)[CH:12]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 86676944HCID 86676944, compound

Product 1

HCID 67466567HCID 67466567, compoundYield 73.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 6-chloro-8-(pyridin-3-yl)imidazo[1,2-b]pyridazine (160 mg, 0.69 mmol) in EtOH (15 mL) was added ammonium formate (175 mg, 2.77 mmol) and palladium hydroxide on carbon (50 mg, 0.07 mmol) (20% wet) under nitrogen. The reaction mixture was heated to 50° C. for 20 min and cooled to room temperature. The reaction mixture was passed through a pad of CELITE® and washed with MeOH. The filtrate was concentrated and the residue was purified by BIOTAGE® (20-60% EtOAc/CH2Cl2, 1.5 L) to give the product (99 mg, 73%). LC (Condition B & C): >95% homogeneity index. LC/MS: Rt=0.31 min. LC/MS (Condition A): 197.21.

Workup

  1. temperaturecooled to room temperature
  2. washwashed with MeOH
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by BIOTAGE® (20-60% EtOAc/CH2Cl2, 1.5 L)

Sources & evidence

ORD record
ord-b680b121cb2643c0895af39aa552b435
Source dataset
uspto-grants-2015_09
Patent number
US09145419B2

Reaction notes

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