Stannane, tributyl(1-ethoxyethenyl)- → 3-Acetyl-1,5-dibenzyl-1H-pyridin-4-one

HRID 1364377Notes

Reaction equation

[CH2:1]([N:8]1[CH:13]=[C:12](Br)[C:11](=[O:15])[C:10]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:28]([O:30]CC)=[CH2:29])CCC>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:28]([C:12]1[C:11](=[O:15])[C:10]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:9][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:13]=1)(=[O:30])[CH3:29]

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of 1,3-dibenzyl-5-bromo-1H-pyridin-4-one 13 (1.31 g, 2.70 mmol), tributyl-(1-ethoxyvinyl)tin (1.80 mL, 5.18 mmol) and dichlorobis(triphenylphosphine)-palladium(II) (0.26 g, 0.37 mmol) in anhydrous DMF (20 mL) was stirred under nitrogen atmosphere at 95° C. for 8 h. The reaction mixture was extracted with ethyl acetate (3×50 mL), washed with 1N HCl (3×50 mL), and solvent distilled off. The residue was purified by flash column chromatography on silica gel (dichloromethane:methanol, 98:2). Yield 1.06 g (90%), yellow oil. 1H NMR (CDCl3, 500 MHz): δ 8.19 (d, 1H, J=2.6), 7.39-7.10 (m, 10H), 6.90 (d, 1H, J=2.5), 4.89 (s, 2H), 3.81 (s, 2H), 2.74 (s, 3H). HRMS (M+H)+ calcd for C21H19NO2 318.1494, found 318.1493.

Workup

extractionThe reaction mixture was extracted with ethyl acetate (3×50 mL)
washwashed with 1N HCl (3×50 mL), and solvent
distillationdistilled off
customThe residue was purified by flash column chromatography on silica gel (dichloromethane:methanol, 98:2)

Sources & evidence

ORD record: ord-e4b1f9d4f87c4b0989466e6b16b00e0a
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07888375B2

Reaction notes

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