O-Xylene → 8-Ethyl-7-fluoro-1-(2-propen-1-yl)-1,5-naphthyridin-2(1H)-one

HRID 656905Notes

Reaction equation

[CH2:1]([C:3]1[C:4]([F:17])=[CH:5][N:6]=[C:7]2[C:12]=1[N:11]=[C:10]([O:13]CC=C)[CH:9]=[CH:8]2)[CH3:2].[C:18]1(C)[C:19](C)=CC=C[CH:23]=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>[CH2:1]([C:3]1[C:4]([F:17])=[CH:5][N:6]=[C:7]2[C:12]=1[N:11]([CH2:19][CH:18]=[CH2:23])[C:10](=[O:13])[CH:9]=[CH:8]2)[CH3:2]

Participants

Conditions

Temperature: 150 °C

Procedure

8-Ethyl-7-fluoro-2-(2-propen-1-yloxy)-1,5-naphthyridine (0.660 g, 2.84 mmol) was dissolved in xylene (14 ml) at rt under argon, whereupon tetrakis(triphenylphosphine)palladium (0.329 g, 0.284 mmol) was added. The reaction was then heated to 150° C. for 30 mins. Reaction was then cooled, a solid then precipitated out which was filtered. The filtrate was then purified by column chromatography on silica gel eluting with 0-100% EtOAc in hexane then 0-20% MeOH in EtOAc gradient to give title compound as a white solid (0.181 g, 27%).

Workup

additionwas added
customReaction
temperaturewas then cooled
customa solid then precipitated out which
filtrationwas filtered
customThe filtrate was then purified by column chromatography on silica gel eluting with 0-100% EtOAc in hexane

Sources & evidence

ORD record: ord-4b91c623732b4dd6bbe63d67594f45de
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071592B2

Reaction notes

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