Ammonium formate → HCID 67468662, compound

HRID 2284367Notes

Reaction equation

HRID 2284367 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][C:16]=2[CH3:17])[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=1.C([O-])=O.[NH4+]>C(O)C.[OH-].[OH-].[Pd+2]>[CH3:17][C:16]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[C:4]1[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=[CH:2][CH:3]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 86676943HCID 86676943, compound

Product 1

HCID 67468662HCID 67468662, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of 6-chloro-8-(4-methylpyridin-3-yl)imidazo[1,2-b]pyridazine (800 mg, 3.27 mmol) in ethanol (80 mL) were added ammonium formate (825 mg, 13.08 mmol) and palladium hydroxide on carbon (459 mg, 0.327 mmol) (20% wet) under nitrogen. The suspension was heated to 70° C. in a sealed pressure bottle for 2 h 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 used for the next step without further purification. 1H NMR (400 MHz, CDCl3) δ ppm 8.53-8.67 (2H, m), 8.43 (1H, d, J=4.53 Hz), 8.09 (1H, d, J=1.26 Hz), 7.81 (1H, d, J=1.01 Hz), 7.31 (1H, d, J=5.04 Hz), 6.99 (1H, d, J=4.53 Hz), 2.33 (3H, s); LC/MS: Rt=0.21 min. LC/MS (Condition A): 211.18.

Workup

  1. temperaturecooled to room temperature
  2. washwashed with MeOH
  3. concentrationThe filtrate was concentrated
  4. customthe residue was used for the next step without further purification

Sources & evidence

ORD record
ord-38d79d6f61014817aac2fbb5b3e5cbf0
Source dataset
uspto-grants-2015_09
Patent number
US09145419B2

Reaction notes

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