Sodium Carbonate → HCID 117839624, compound

HRID 1477664Notes

Reaction equation

HRID 1477664 reaction equation
[CH3:1][C:2]1([C:23]([O:25][CH3:26])=[O:24])[C:7](OS(C(F)(F)F)(=O)=O)=[CH:6][CH2:5][N:4]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:3]1.[F:27][C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1.[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+]>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.C(COC)OC>[F:27][C:28]1[CH:33]=[CH:32][C:31]([C:7]2[C:2]([CH3:1])([C:23]([O:25][CH3:26])=[O:24])[CH2:3][N:4]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:5][CH:6]=2)=[CH:30][CH:29]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 433294Lithium ChlorideHCID 117839690HCID 117839690, compound

Product 1

HCID 117839624HCID 117839624, compoundYield 80%

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a dimethoxyethane solution (6.0 mL) of 3-methyl 1-tert-butyl 3-methyl-4-{[(trifluoromethyl)sulfonyl]oxy}-2,3-dihydropyridine-1,3(6H)-dicarboxylate (300 mg, 0.743 mmol) synthesized in Reference Synthesis Example 273, 4-fluorophenylboronic acid (347 mg, 2.14 mmol), tetrakis(triphenylphosphine)palladium (0) (102 mg, 0.0880 mmol), lithium chloride (321 mg, 7.57 mmol), and 2 M sodium carbonate aqueous solution (2.5 mL) were added and the resultant mixture was stirred at 90° C. for 3 hours. After completion of the reaction, water was added to the reaction solution and extraction from the resultant mixture with ethyl acetate was performed. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to obtain the title compound (207 mg, yield 80%).

Workup

  1. additionwere added
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-381985bc005c44dba2c8ac65f9751423
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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