Water → HCID 11276259, compound

HRID 1818892Notes

Reaction equation

HRID 1818892 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.C([Sn](CCCC)(CCCC)[C:19]1[O:20][CH:21]=[CH:22][CH:23]=1)CCC.[F-].[K+].O>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>[CH3:13][C:4]1[CH:5]=[C:6]2[CH2:11][CH2:10][O:9][C:8](=[O:12])[C:7]2=[C:2]([C:19]2[O:20][CH:21]=[CH:22][CH:23]=2)[N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 522689Potassium FluorideHCID 43936882-(Tributylstannyl)furanHCID 11217833HCID 11217833, compound

Product 1

HCID 11276259HCID 11276259, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 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) and Pd(PPh3)4 (146 mg, 0.127 mmol) were dissolved in 12 mL of anhydrous toluene, dropwisely added with 2-(tributylstannyl)furan (0.80 mL, 2.530 mmol) and then heated to reflux for about 15 hours under the nitrogen atmosphere. The mixture was added with 15 mL of 2% KF solution and 20 mL of distilled water while stirring at 0° C. and then extracted twice with 50 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 225 mg (78%) of 6-methyl-8-furan-2-yl-3,4-dihydro-pyrano[3,4-c]pyridine-1-on was obtained in white solid.

Workup

  1. temperatureheated
  2. temperatureto reflux for about 15 hours under the nitrogen atmosphere
  3. extractionextracted twice with 50 mL of methylene chloride
  4. customThe resulting organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-331fe164df484b238c5416fbc47c2f6a
Source dataset
uspto-grants-2009_10
Patent number
US07601736B2

Reaction notes

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