Potassium Carbonate → HCID 11482284, compound

HRID 1818893Notes

Reaction equation

HRID 1818893 reaction equation
Cl[C:2]1[N:3]=[C:4]([CH3:13])[CH:5]=[C:6]2[CH2:11][CH2:10][O:9][C:8](=[O:12])[C:7]=12.[F:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>C1(C)C=CC=CC=1.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.O>[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:2]2[N:3]=[C:4]([CH3:13])[CH:5]=[C:6]3[CH2:11][CH2:10][O:9][C:8](=[O:12])[C:7]=23)=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 2856454-Fluorophenylboronic acidHCID 11217833HCID 11217833, compound

Product 1

HCID 11482284HCID 11482284, compoundYield 42%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

8-chloro-6-methyl-3,4-dihydro-pyrano[3,4-c]pyridine-1-on (250 mg, 1.265 mmol), 4-fluorophenyl boronic acid (265 mg, 1.898 mmol), Pd(PPh3)4 (146 mg, 0.127 mmol) and anhydrous potassium carbonate (350 mg, 2.530 mmol) were suspended in 10 mL of anhydrous toluene and then refluxed for about 15 hours under the nitrogen atmosphere. The mixture was added with 20 mL of a saturated solution of ammonium chloride and 10 mL of distilled water while stirring at 0° C. and then extracted twice with 60 mL of methylene chloride. The resulting organic layer was dried using anhydrous sodium sulfate, filtered and concentrated. A silica gel column chromatography (5% EtOAc/MC) was performed on the resulting residue and 135 mg (42%) of 8-(4-fluorophenyl)-6-methyl-3,4-dihydro-pyrano[3,4-c]pyridine-1-on was obtained in pale yellow solid.

Workup

  1. temperaturerefluxed for about 15 hours under the nitrogen atmosphere
  2. extractionextracted twice with 60 mL of methylene chloride
  3. customThe resulting organic layer was dried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ac548344a813428d84f5ccfe250ab66b
Source dataset
uspto-grants-2009_10
Patent number
US07601736B2

Reaction notes

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