Chloroform → HCID 59340121, compound

HRID 13644Notes

Reaction equation

HRID 13644 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:22])=[C:7]([C:14]([NH:16][CH2:17][C:18]([O:20]C)=[O:19])=[O:15])[C:8](=[O:13])[N:9]2[CH3:12])=[CH:4][CH:3]=1.C(Cl)(Cl)Cl.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[NH:61]1[CH2:66][CH2:65][O:64][CH2:63][CH2:62]1.CC(C)([O-])C.[Na+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[OH:22][C:6]1[C:5]2[C:10](=[CH:11][C:2]([N:61]3[CH2:66][CH2:65][O:64][CH2:63][CH2:62]3)=[CH:3][CH:4]=2)[N:9]([CH3:12])[C:8](=[O:13])[C:7]=1[C:14]([NH:16][CH2:17][C:18]([OH:20])=[O:19])=[O:15]

Participants

8

Reactant 5

HCID 6212ChloroformHCID 8083MorpholineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23676156Sodium t-butoxideHCID 54681697Methyl 2-(7-bromo-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetate

Product 1

HCID 59340121HCID 59340121, compoundYield 18.4%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of methyl 2-(7-bromo-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetate (100 mg, 271 μmol), Pd2 dba3.CHCl3 (28 mg, 27 μmol), X-Phos (26 mg, 54 μmol) and morpholine (71 μl, 813 μmol) in 1,4-dioxane (3 ml) was treated with sodium tert-butoxide (104 mg, 1084 μmol). The reaction was stirred at 80° C. in a sealed tube. After 24 hours, the suspension was cooled to 23° C., filtered through celite (extensively washing with methanol), the filtrate concentrated in vacuo and purified by silica gel chromatography after adsorption onto silica (eluant: 10% methanol/dichloromethane+1% AcOH), affording 18 mg (18%) of 2-(4-Hydroxy-1-methyl-7-morpholino-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetic acid as a greenish-white solid.

Workup

  1. temperaturethe suspension was cooled to 23° C.
  2. filtrationfiltered through celite (
  3. washextensively washing with methanol), the filtrate
  4. concentrationconcentrated in vacuo
  5. custompurified by silica gel chromatography after adsorption onto silica (eluant: 10% methanol/dichloromethane+1% AcOH)

Sources & evidence

ORD record
ord-ca1e41042f8b4f35a81a3b998b771994
Source dataset
uspto-grants-2010_06
Patent number
US07728130B2

Reaction notes

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