Stannane, tributyl(1-ethoxyethenyl)- → HCID 58235010, compound

HRID 1947364Notes

Reaction equation

HRID 1947364 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:20]([O:22][CH3:23])=[O:21])[CH:5]=[C:6]2[C:11]=1[O:10][C:9]([N:12]1[CH2:17][CH2:16][O:15][C@H:14]([CH3:18])[CH2:13]1)=[CH:8][C:7]2=[O:19].C([Sn](CCCC)(CCCC)[C:29]([O:31]CC)=[CH2:30])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:29]([C:2]1[CH:3]=[C:4]([C:20]([O:22][CH3:23])=[O:21])[CH:5]=[C:6]2[C:11]=1[O:10][C:9]([N:12]1[CH2:17][CH2:16][O:15][C@H:14]([CH3:18])[CH2:13]1)=[CH:8][C:7]2=[O:19])(=[O:31])[CH3:30]

Participants

5

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 58235000(R)-methyl 8-bromo-2-(2-methylmorpholino)-4-oxo-4H-chromene-6-carboxylate

Product 1

HCID 58235010HCID 58235010, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

Methyl 8-bromo-2-((R)-2-methylmorpholino)-4-oxo-4H-chromene-6-carboxylate (1.45 g, 3.79 mmol), bis(triphenylphosphine) palladium(II) chloride (0.107 g, 0.15 mmol) and tributyl(1-ethoxyvinyl)stannane (1.346 mL, 3.98 mmol) in 1,4-dioxane (20 mL) were degased, purged with argon and heated to 90° C. for 4 hrs. After cooling to RT, HCl2N (1.9 mL, 3.79 mmol) was added and the mixture was left to stir for 1 h. The reaction mixture was concentrated, suspended in water, neutralised with NaHCO3 and extracted with DCM. The combined organic phases were washed with water, brine, dried over magnesium sulfate and concentrated. The crude product was triturated with n-heptane, filtered and retriturated with ether, filtered and dried to give methyl 8-acetyl-2-((R)-2-methylmorpholino)-4-oxo-4H-chromene-6-carboxylate (1.15 g, 88%) as a grey solid. Mass Spectrum: M+H+ 346.

Workup

  1. custompurged with argon
  2. temperatureAfter cooling to RT
  3. waitthe mixture was left
  4. concentrationThe reaction mixture was concentrated
  5. extractionextracted with DCM
  6. washThe combined organic phases were washed with water, brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe crude product was triturated with n-heptane
  10. filtrationfiltered
  11. customretriturated with ether
  12. filtrationfiltered
  13. customdried

Sources & evidence

ORD record
ord-0ed51b8ba2f44f34a05fe0dcadcd7b7f
Source dataset
uspto-grants-2013_03
Patent number
US08399460B2

Reaction notes

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