Potassium Fluoride → HCID 11265076, compound

HRID 1818906Notes

Reaction equation

C([Sn](CCCC)(CCCC)[C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)CCC.Cl[C:20]1[CH:21]=[C:22]2[CH2:30][CH2:29][O:28][C:27](=[O:31])[C:23]2=[C:24]([CH3:26])[N:25]=1.[F-].[K+]>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.C1(C)C=CC=CC=1>[CH3:26][C:24]1[N:25]=[C:20]([C:6]2[S:7][CH:8]=[CH:9][CH:10]=2)[CH:21]=[C:22]2[CH2:30][CH2:29][O:28][C:27](=[O:31])[C:23]=12

Participants

Conditions

Temperature: 100 °C

Procedure

2-(tributylstannyl)thiophene (940 mg, 2.52 mmol) was dropwisely added to a toluene solution of 6-chloro-8-methyl-3,4-dihydro-pyrano[3,4-c]pyridine-1-on (250 mg, 1.26 mmol) and Pd(PPh3)4 (146 mg, 0.13 mmol), and then stirred overnight at 100° C. The solution was cooled down to room temperature, added with 15 mL of 0.4M KF solution and then extracted with methylene chloride. The resulting organic layer was dried with anhydrous sodium sulfate, filtered and then concentrated under reduced pressure. A silica gel column chromatography (33% EtOAC/Hexanes) was performed on the resulting residue and obtained 298 mg (96%) of 8-methyl-6-(thiophene-2-yl)-3,4-dihydro-pyrano[3,4-c]pyridine-1-on in yellow solid.

Workup

temperatureThe solution was cooled down to room temperature
extractionextracted with methylene chloride
dry with materialThe resulting organic layer was dried with anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-2f55cc6a508947c7b982b3e49b1f9a2e
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601736B2

Reaction notes

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