Sodium Carbonate → HCID 117848989, compound

HRID 1477635Notes

Reaction equation

HRID 1477635 reaction equation
Br[C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([Cl:10])=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH:20]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[NH4+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C.O.O1CCOCC1>[Cl:10][C:5]1[CH:4]=[CH:3][C:2]([C:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH:20]=2)=[N:7][C:6]=1[O:8][CH3:9]

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 584523026-Bromo-3-chloro-2-methoxypyridine

Product 1

HCID 117848989HCID 117848989, compoundYield 97%

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a 1,4-dioxane (50 mL)-water (10 mL) solution of 6-bromo-3-chloro-2-methoxypyridine (1.98 g, 8.90 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (2.50 g, 8.09 mmol), and sodium carbonate (1.71 g, 16.1 mmol), tetrakis(triphenylphosphine)palladium (0) (467 mg, 0.400 mmol) was added under argon atmosphere and the resultant mixture was stirred at 100° C. for 3 hours. After completion of the reaction, saturated ammonium chloride aqueous solution was added to the reaction solution and extraction from the resultant mixture with ethyl acetate was performed. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1) to obtain the title compound (2.55 g, yield 97%).

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-cfc8eb8e2fe444c999c84fdcf1138b62
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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