Triethylamine → 3-Quinolin-6-yl-acrylic acid ethyl ester

HRID 655204Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[C:12]([O:16][CH2:17][CH3:18])(=[O:15])[CH:13]=[CH2:14].C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C)C=O>[CH2:17]([O:16][C:12](=[O:15])[CH:13]=[CH:14][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2)[CH3:18]

Participants

Conditions

Temperature: 100 °C

Procedure

A vial under nitrogen atmosphere was charged with 6-bromo-quinoline (1 g, 4.8 mmol) and dimethylformamide (15 mL), followed by ethyl acrylate (2.1 mL, 19.2 mmol), triethylamine (6.7 mL, 48 mmol), and palladium (II) acetate (32 mg, 0.142 mmol). The reaction mixture was stirred at 100° C. for 5 h, then the hot mixture was filtered over celite and the filtrate was concentrated in vacuo. The residue was partitioned between water and ethyl acetate. The organic layer was washed with saturated aqueous solution of ammonium chloride, saturated aqueous solution of sodium bicarbonate, then brine. The organic layer was then adsorbed on silica gel. Purification on silica gel with 10-80% gradient of ethyl acetate in hexane provided 952 mg of product as a yellow oil. 1H NMR 500 MHz (DMSO) δ 1.28 (t, 3H), 4.20 (q, 2H), 6.82 (d, 1H), 7.58 (d, 1H), 7.84 (d, 1H), 8.01 (d, 1H), 8.16 (dd, 1H), 8.30 (d, 1H), 8.37 (dd, 1H), 8.93 (dd, 1H); MS (m/z) 228 [M+H+]+.

Workup

filtrationthe hot mixture was filtered over celite
concentrationthe filtrate was concentrated in vacuo
customThe residue was partitioned between water and ethyl acetate
washThe organic layer was washed with saturated aqueous solution of ammonium chloride, saturated aqueous solution of sodium bicarbonate
customPurification on silica gel with 10-80% gradient of ethyl acetate in hexane

Sources & evidence

ORD record: ord-9f861a8b07b74885a05fcdc7a6b5ca29
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071581B2

Reaction notes

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