Sodium Carbonate → HCID 70872510, compound

HRID 1616359Notes

Reaction equation

HRID 1616359 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][N:28]([CH3:30])[CH3:29])=[CH:23][CH: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([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.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>[C:21]1([C:2]2[CH:3]=[C:4]([CH:18]=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([CH2:27][N:28]([CH3:30])[CH3:29])=[CH:23][CH:22]=3)[N:20]=2)[C:5]([NH:7][CH2:8][C:9]2[C:10](=[O:17])[NH:11][C:12]([CH3:16])=[CH:13][C:14]=2[CH3:15])=[O:6])[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 61668Boronic AcidHCID 86672643HCID 86672643, compound

Product 1

HCID 70872510HCID 70872510, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

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-(4-((dimethylamino)methyl)phenyl)isonicotinamide (0.11 g, 0.25 mmol), boronic acid (0.059 g, 0.27 mmol) in dioxane/water mixture (3 mL+1.5 mL), Na2CO3 (0.098 g, 3.6 mmol) was added and reaction mass purged with argon for 15 min. Then Pd(PPh3)4 (0.028 g, 0.025 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 2-(cyclohex-1-en-1-yl)-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-(4-((dimethylamino)methyl)phenyl)isonicotinamide.

Workup

  1. customreaction mass
  2. custompurged with argon for 15 min
  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-55bcc46d35ce45d7b53c83e01e318eee
Source dataset
uspto-grants-2014_07
Patent number
US08765732B2

Reaction notes

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