HCID 66653371, compound → HCID 66653197, compound

HRID 535467Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:4]([CH3:34])=[C:5]([C:12]([C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[N:20](CC=C)[C:19]([CH3:27])=[C:18]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:17]3=[O:33])=[O:13])[N:6]2[C:11]=1[CH:10]=[CH:9][CH:8]=[CH:7]2>O>[CH3:1][O:2][C:3]1[C:4]([CH3:34])=[C:5]([C:12]([C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[NH:20][C:19]([CH3:27])=[C:18]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:17]3=[O:33])=[O:13])[N:6]2[C:11]=1[CH:10]=[CH:9][CH:8]=[CH:7]2

Participants

Conditions

Temperature: 120 °C

Procedure

6.7 mg (0.02 mmol) of dichloro(2,6,10-dodecatriene)-1,12-diyl ruthenium(IV) are added, at ambient temperature under an inert atmosphere, to 0.307 (0.67 mol) of ethyl 6-[(1-methoxy-2-methylindolizin-3-yl)carbonyl]-2-methyl-4-oxo-1-prop-2-en-1-yl-1,4-dihydroquinoline-3-carboxylate in 12 ml of a mixture of DMFt-butanol and water (1/1). The reaction medium is microwave-heated for 30 minutes at 120° C. and then extracted with ethyl acetate. The organic phase obtained is washed with a saturated aqueous solution of sodium chloride, dried over sodium sulphate, filtered, and concentrated under reduced pressure. The precipitate obtained is purified by silica gel column chromatography, elution being carried out with a dichloromethane/methanol (95/5) mixture. 94 mg of a yellow solid are obtained.

Workup

extractionextracted with ethyl acetate
customThe organic phase obtained
washis washed with a saturated aqueous solution of sodium chloride
dry with materialdried over sodium sulphate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe precipitate obtained
customis purified by silica gel column chromatography, elution

Sources & evidence

ORD record: ord-926812100daa4b2daf807011583b8d7d
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859544B2

Reaction notes

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