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

HRID 2120646Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[C:10]([O:14][CH2:15][CH3:16])(=[O:13])[CH:11]=[CH2:12].C(N(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>[CH3:9][O:8][C:5]1[N:6]=[CH:7][C:2]([CH:12]=[CH:11][C:10]([O:14][CH2:15][CH3:16])=[O:13])=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of the 5-bromo-2-methoxypyridine (1-2) (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 1-3 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-4b9560eec994478096a3f39f45b3f55b
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06693101B2

Reaction notes

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