Tributylvinyltin → 6-Ethenyl-3,4-dihydro-1,8-naphthyridin-2(1H)-one

HRID 1271704Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.[CH2:13]([Sn](CCCC)(CCCC)C=C)[CH2:14]CC>CN(C=O)C.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>[CH:13]([C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2)=[CH2:14]

Participants

Conditions

Temperature: 105 °C

Procedure

6-Bromo-3,4-dihydro-1H-[1,8]naphthyridin-2-one (113e) (4.6 g, 20.3 mmole) and tributyl(vinyl)tin (7.7 g, 24.4 mmole) were dissolved in DMF (200 mL) and the solution was degassed with nitrogen. (Ph3P)4Pd (590 mg, 0.5 mmole) was added to the solution. The reaction was heated to 105° C. under nitrogen overnight, then was cooled to room temperature and filtered through a sintered glass funnel. The filtrate was washed with NH4OH and extracted with EtOAc (2×150 mL). The combined organic phases were washed with brine, dried over Na2SO4 and concentrated in vacuo to afford the title compound (2.1 g, 60%) as an off white solid: MS (ES) m/e 175 (M+H)+.

Workup

customthe solution was degassed with nitrogen
temperaturewas cooled to room temperature
filtrationfiltered through a sintered glass funnel
washThe filtrate was washed with NH4OH
extractionextracted with EtOAc (2×150 mL)
washThe combined organic phases were washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-c0d8523c87354d54ba36574e0cccb338
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07205408B2

Reaction notes

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