Sodium Carbonate → HCID 86672644, compound

HRID 1616361Notes

Reaction equation

HRID 1616361 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[N:20]=1)[C:5]([NH:7][CH2:8][C:9]1[C:10](=[O:17])[NH:11][C:12]([CH3:16])=[CH:13][C:14]=1[CH3:15])=[O:6].B(O)O.[C:30]([O-:33])([O-])=O.[Na+].[Na+].O1[CH2:41][CH2:40]OCC1.O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:15][C:14]1[CH:13]=[C:12]([CH3:16])[NH:11][C:10](=[O:17])[C:9]=1[CH2:8][NH:7][C:5](=[O:6])[C:4]1[CH:18]=[C:19]([N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[N:20]=[C:2]([C:41]2[CH:40]=[CH:5][C:4]([CH:30]=[O:33])=[CH:3][CH:2]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 61668Boronic AcidHCID 218864351,4-Dioxane--water (1/1)HCID 86672645HCID 86672645, compound

Product 1

HCID 86672644HCID 86672644, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 2-chloro-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-(piperidin-1-yl)isonicotinamide (0.6 g, 1.6 mmol), boronic acid (0.263 g, 1.76 mmol) in dioxane/water mixture (15 mL+5 mL), Na2CO3 (0.61 g, 5.76 mmol) was added and reaction mass purged for 15 min with argon. Then Pd(PPh3)4 (0.184 g, 0.16 mmol) was added and argon was purged again for 10 min. Reaction mass was heated at 100° C. for 3 h. On completion, reaction mass filtered through celite and celite bed washed with ethyl acetate. Combined filtrates were dried over Na2SO4 and solvent removed under reduced pressure to afford crude material which was purified by column over silica gel to obtain N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2-(4-formylphenyl)-6-(piperidin-1-yl)isonicotinamide (0.5 g, 71%).

Workup

  1. customreaction mass
  2. custompurged for 15 min with argon
  3. customargon was purged again for 10 min
  4. customReaction mass
  5. customOn completion, reaction mass
  6. filtrationfiltered through celite and celite bed
  7. washwashed with ethyl acetate
  8. dry with materialCombined filtrates were dried over Na2SO4 and solvent
  9. customremoved under reduced pressure
  10. customto afford crude material which
  11. customwas purified by column over silica gel

Sources & evidence

ORD record
ord-6f8ea8b538ad4f53bd44c2715ef4ae52
Source dataset
uspto-grants-2014_07
Patent number
US08765732B2

Reaction notes

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