Triethylamine → Ethyl 3-(6-methoxy-3-pyridyl)acrylate

HRID 1108414Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:10])[CH2:5][CH:6](N)[CH:7]=[CH2:8])[CH3:2].[C:11]([O:15][CH2:16]C)(=O)[CH:12]=C.[CH2:18]([N:20](CC)CC)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:16][O:15][C:11]1[N:20]=[CH:18][C:7]([CH:6]=[CH:5][C:4]([O:3][CH2:1][CH3:2])=[O:10])=[CH:8][CH:12]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of the 5-bromo-2-methoxypyridine 18-2 (74.3 g, 0.4 mol), ethyl acrylate (150 mL, 1.4 mol), triethylamine (150 mL, 1.08 mol), palladium acetate (10 g, 0.045 mol) and tri-o-tolylphosphine (20 g, 0.066 mol) in 100 mL acetonitrile was degassed with argon for 10 minutes. The mixture was heated at 90° C. for 12 hr then the volatiles were removed in vacuo. Toluene (300 mL) was added and the mixture concentrated again. Diethyl ether (300 mL) was added and the mixture filtered through a pad of silica gel eluting with 800 mL of diethyl ether. After removal of the diethyl ether, the residue was chromatographed on silica gel eluting with EtOAc/hexane, 1:19 then 1:14 then 1:9, to give 19-3 as a yellow solid.

Workup

customthe volatiles were removed in vacuo
additionToluene (300 mL) was added
concentrationthe mixture concentrated again
additionDiethyl ether (300 mL) was added
filtrationthe mixture filtered through a pad of silica gel eluting with 800 mL of diethyl ether
customAfter removal of the diethyl ether
customthe residue was chromatographed on silica gel eluting with EtOAc/hexane, 1:19

Sources & evidence

ORD record: ord-1b8eee3e5b8e4e11bf5d7d06989909b3
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06066648

Reaction notes

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