1,4-Dioxane → 4-(1-Acetyl-1,2,3,6-tetrahydropyridin-4-yl)furo[3,2-c]pyridine

HRID 2184802Notes

Reaction equation

[Li+].[Cl-].[C:3]([N:6]1[CH2:11][CH:10]=[C:9]([Sn](CCCC)(CCCC)CCCC)[CH2:8][CH2:7]1)(=[O:5])[CH3:4].O1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]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>[C:3]([N:6]1[CH2:11][CH:10]=[C:9]([C:3]2[C:4]3[CH:30]=[CH:29][O:28][C:27]=3[CH:26]=[CH:7][N:6]=2)[CH2:8][CH2:7]1)(=[O:5])[CH3:4]

Participants

Conditions

Temperature: 100 °C

Procedure

7 equivalents of LiCl, and then 0.03 equivalents of Pd(PPh3)4 are added, under a stream of argon, to a solution of 52.3 mmol of the product of Preparation 1 and 1.2 equivalents of the product obtained in Step B in 800 ml of dioxane. The reaction mixture is heated to 100° C. and 0.03 equivalent of Pd(PPh3)4 is added in succession, after reaction for 12 hours, 24 hours and 48 hours, and the reaction mixture is maintained at 100° C. for an additional 24 hours. After cooling, filtration over Celite and concentration under reduced pressure, chromatography of the residue on silica gel (dichloromethane/ethanol: 97/3) enables the expected product to be isolated; the product is then crystallised in pentane.

Workup

customafter reaction for 12 hours
temperature24 hours and 48 hours, and the reaction mixture is maintained at 100° C. for an additional 24 hours
temperatureAfter cooling
filtrationfiltration
concentrationover Celite and concentration under reduced pressure, chromatography of the residue on silica gel (dichloromethane/ethanol: 97/3)
customto be isolated
customthe product is then crystallised in pentane

Sources & evidence

ORD record: ord-57166cb5a46e4819b8d80049042a324a
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06399616B1

Reaction notes

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