Potassium Carbonate → HCID 66633006, compound

HRID 416573Notes

Reaction equation

HRID 416573 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[C:12](=[O:22])[N:13]([CH2:18][CH2:19][CH2:20][CH3:21])[CH:14]=[C:15](I)[CH:16]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]1(OB(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CN(C=O)C.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(OCC)(=O)C>[CH2:1]([NH:8][C:9]([C:11]1[C:12](=[O:22])[N:13]([CH2:18][CH2:19][CH2:20][CH3:21])[CH:14]=[C:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:16]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 78412Phenyl dihydrogen orthoborateHCID 66632789HCID 66632789, compound

Product 1

HCID 66633006HCID 66633006, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-butyl-5-iodo-2-oxo-1,2-dihydropridine-3-carboxylic acid benzylamide (3-067) (100 mg) in DMF (2.0 mL) were added Pd(PPh3)4 (20 mg), phenyl boric acid (89 mg), and an aqueous solution of potassium carbonate (2 mole/L, 0.24 mL) at room temperature. After stirred at 90° C. for 18 h, to the reaction mixture were added a saturated aqueous solution of ammonium chloride and ethyl acetate. The organic layer was separated and the aqueous layer was extracted three times with ethyl acetate, and the combined organic layers were washed with water and brine, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The obtained crude product was purified by the preparative thin-layer chromatography (toluene/acetone=7/1) to give 1-butyl-2-oxo-5-phenyl-1,2-dihydropridine-3-carboxylic acid benzylamide (3-068) (77 mg, 88%) as an oil.

Workup

  1. customat room temperature
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted three times with ethyl acetate
  4. washthe combined organic layers were washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe obtained crude product
  8. customwas purified by the preparative thin-layer chromatography (toluene/acetone=7/1)

Sources & evidence

ORD record
ord-35dcbb9f33f746fd9dde57dd9d828130
Source dataset
uspto-grants-2012_01
Patent number
US08088924B2

Reaction notes

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