Ammonium formate → 2,3-Bis(3-fluoro-4-methylphenyl)-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine

HRID 406255Notes

Reaction equation

HRID 406255 reaction equation
C([O-])=O.[NH4+].[F:5][C:6]1[CH:7]=[C:8]([C:13]2[N:14]=[C:15]3[CH:30]=[CH:29][CH:28]=[N:27][C:16]3=[N:17][C:18]=2[C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[C:21]([F:26])[CH:20]=2)[CH:9]=[CH:10][C:11]=1[CH3:12]>CO.[OH-].[OH-].[Pd+2]>[F:5][C:6]1[CH:7]=[C:8]([C:13]2[N:14]=[C:15]3[CH2:30][CH2:29][CH2:28][NH:27][C:16]3=[N:17][C:18]=2[C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[C:21]([F:26])[CH:20]=2)[CH:9]=[CH:10][C:11]=1[CH3:12]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 666659662,3-Bis(3-fluoro-4-methylphenyl)pyrido[2,3-b]pyrazine

Product 1

HCID 666661992,3-Bis(3-fluoro-4-methylphenyl)-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst2×HCID 887MethanolSolvent

Procedure

To Pd(OH)2 (20% on carbon, 50% water wet) (30 mg, 0.214 mmol) and ammonium formate (557 mg, 8.84 mmol) was added a solution of 2,3-bis(3-fluoro-4-methylphenyl)pyrido[2,3-b]pyrazine (step 1)(307 mg, 0.884 mmol) in MeOH (3 ml) and the reaction mixture was heated to reflux for 5 h. A further portion of Pd(OH)2 (20% on carbon, 50% water wet) (30 mg, 0.214 mmol) was added and the mixture was heated to reflux for 6 h. The reaction mixture was filtered through Celite® (filter material) and washed with MeOH and EtOAc. The filtrate was concentrated in vacuo to afford the title compound as a yellow solid;

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 5 h
  3. temperaturethe mixture was heated
  4. temperatureto reflux for 6 h
  5. filtrationThe reaction mixture was filtered through Celite® (filter material)
  6. washwashed with MeOH and EtOAc
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-65deeb402a5d49c9b8e6ebe7ccb3c23c
Source dataset
uspto-grants-2014_06
Patent number
US08754085B2

Reaction notes

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