Stannane, tributyl(1-ethoxyethenyl)- → 8-acetyl-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid

HRID 572718Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:19]([OH:21])=[O:20])[CH:5]=[C:6]2[C:11]=1[O:10][C:9]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)=[CH:8][C:7]2=[O:18].C([Sn](CCCC)(CCCC)[C:27]([O:29]CC)=[CH2:28])CCC>O1CCOCC1.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:27]([C:2]1[CH:3]=[C:4]([C:19]([OH:21])=[O:20])[CH:5]=[C:6]2[C:11]=1[O:10][C:9]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)=[CH:8][C:7]2=[O:18])(=[O:29])[CH3:28]

Participants

Conditions

Temperature: 100 °C

Procedure

Bis(triphenylphosphine) palladium (II) chloride (12.78 mg, 0.02 mmol) was added to a stirred mixture of 8-bromo-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid (215 mg, 0.61 mmol) and tributyl(1-ethoxyvinyl)stannane (0.226 mL, 0.67 mmol) in 1,4-dioxane (5 mL) and the mixture was purged with nitrogen. The resulting mixture was stirred at 100° C. for 3 hrs. HCl 2N (0.5 mL) was added and the reaction mixture was stirred at 50° C. for 25 minutes then allowed to cool to room temperature and concentrated under vacuum. The product was diluted with diethyl ether and pentane to afford a solid, which was collected by filtration and washed with ether/pentane to give 8-acetyl-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid (200 mg, 104%) as a beige solid. Mass Spectrum: M+H+ 318.

Workup

customthe mixture was purged with nitrogen
additionHCl 2N (0.5 mL) was added
stirringthe reaction mixture was stirred at 50° C. for 25 minutes
temperatureto cool to room temperature
concentrationconcentrated under vacuum
additionThe product was diluted with diethyl ether and pentane
customto afford a solid, which
filtrationwas collected by filtration
washwashed with ether/pentane

Sources & evidence

ORD record: ord-5bf5c3926b774c57b8f80dce3e16963a
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029374B2

Reaction notes

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