Citric Acid → HCID 57879499, compound

HRID 1673552Notes

Reaction equation

HRID 1673552 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[CH:6]=[CH:5]2.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C:20]([NH:28][C:29]1[CH:38]=[C:37](Br)[CH:36]=[CH:35][C:30]=1[C:31]([O:33][CH3:34])=[O:32])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C.C(OCC)(=O)C.C1(C)C=CC=CC=1>[C:20]([NH:28][C:29]1[CH:38]=[C:37]([O:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[N:7]([CH3:11])[CH:6]=[CH:5]3)[CH:36]=[CH:35][C:30]=1[C:31]([O:33][CH3:34])=[O:32])(=[O:27])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

9

Reactant 4

HCID 311Citric AcidHCID 62657Potassium Phosphate, TribasicHCID 108445251-Methyl-1H-indol-5-olHCID 57879335Methyl 2-(benzamido)-4-bromobenzoate

Product 1

HCID 57879499HCID 57879499, compoundYield 88.5%

Reagents, catalysts & solvents 4

HCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 11618717Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphaneCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

26 mg of 5-hydroxy-1-methyl-1H-indole, 64 mg of tripotassium phosphate, 3.8 mg of 2-(di-tert-butylphosphino)-2′,4′,6′-triisopropylbiphenyl and 5.5 mg of tris(dibenzylideneacetone) dipalladium (0) were added to 1.0 mL of toluene solution containing 50 mg of methyl 2-(benzamido)-4-bromobenzoate at zoom temperature, and the resulting mixture was heated to reflux under nitrogen atmosphere for 2 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and 10% citric acid aqueous solution were added and insoluble were removed by filtration. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium chloride aqueous solution, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia chemical Ltd., eluent; hexane:ethyl acetate=5:1] to obtain 53 mg of methyl 2-(benzamido)-4-(1-methyl-1H-indol-5-yloxy)benzoate as pale yellow solid.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux under nitrogen atmosphere for 2 hours
  3. custominsoluble were removed by filtration
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. washafter washed with a saturated sodium chloride aqueous solution
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia chemical Ltd., eluent; hexane:ethyl acetate=5:1]

Sources & evidence

ORD record
ord-4f2963feaa3a4fce9c58e345cf2813a3
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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