Diethyl Ether → HCID 23436313, compound

HRID 2121190Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[N:8]([CH3:10])[CH3:9].[CH:11]([Sn](CCCC)(CCCC)CCCC)=[CH2:12].CCOCC.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1.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.O>[CH:11]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[N:8]([CH3:10])[CH3:9])=[CH2:12]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of the 3-bromo-4-dimethylaminopyridine prepared in Example 214A (1.29 g, 6.39 mmol) vinyltributyltin (2.23 g, 7.02 mmol), bis(triphenylphosphine)palladium(II) chloride (224 mg, 0.32 mmol) in toluene (10 mL) was heated at 100° C. for 12 hours. To the stirring reaction mixture at room temperature was added ether (30 mL), water (0.2 mL) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.5 mL). The resulting mixture was filtered through silica gel (15 g), rinsed with ethyl acetate, and concentrated in vacua. The residue was purified by column chromatography (50% ethyl acetate-hexanes, then ethyl acetate) to give 3-vinyl-4-dimethylaminopyridine (1.11 g, contaminated with about 10 mol % of tributyltin. derivatives). 1H NMR (300 MHz, CDCl3) δ 8.39 (s, 1H), 8.26 (d, 1H), 6.77 (dd, 1H), 6.70 (d, 1H), 5.65 (dd, 1H), 5.29 (dd, 1H), 2.87 (s, 6H).

Workup

customTo the stirring reaction mixture at room temperature
filtrationThe resulting mixture was filtered through silica gel (15 g)
washrinsed with ethyl acetate
concentrationconcentrated in vacua
customThe residue was purified by column chromatography (50% ethyl acetate-hexanes

Sources & evidence

ORD record: ord-607c0103e04b4ce399aa13677a783e88
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06693123B2

Reaction notes

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