Potassium Carbonate → HCID 68650610, compound

HRID 402282Notes

Reaction equation

HRID 402282 reaction equation
Br[C:2]1[CH:20]=[CH:19][C:5]2[CH:6]([C:15]([O:17][CH3:18])=[O:16])[CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH2:12][CH2:13][CH3:14])[C:4]=2[CH:3]=1.[CH2:21]([O:25][CH2:26][CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32](OB(O)O)=[CH:31][CH:30]=1)[CH2:22][CH2:23][CH3:24].[C:39](=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:21]([O:25][CH2:26][CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([C:20]2[CH:2]=[CH:3][C:4]3[N:11]([CH2:12][CH2:13][CH3:14])[CH2:10][CH2:9][CH2:8][CH2:7][C:6]([C:15]([O:17][CH3:18])=[O:16])=[CH:39][C:5]=3[CH:19]=2)=[CH:31][CH:30]=1)[CH2:22][CH2:23][CH3:24]

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 230910874-(2-Butoxyethoxy)phenylboric acidHCID 68650161HCID 68650161, compound

Product 1

HCID 68650610HCID 68650610, compoundYield 75.9%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

A suspension of methyl 9-bromo-1-propyl-2,3,4,5-tetrahydro-1H-1-benzoazocine-6-carboxylate (2.1 g) and 4-(2-butoxyethoxy)phenyl boric acid (1.84 g), and potassium carbonate (2.14 g) in toluene (25 ml), ethanol (2.5 ml) and water (2.5 ml) was stirred under argon atmosphere for 1 hour and then tetrakis(triphenylphosphine)palladium (343 mg) was added. The mixture was refluxed for 5 hours. After returning to room temperature, water was added and the reaction mixture was and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried with magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1→hexane:ethyl acetate=9:1) to give methyl 9-(4-(2-butoxyethoxy)phenyl)-1-propyl-2,3,4,5-tetrahydro-1H-1-benzoazonin-6-carboxylate (2.18 g) as a yellow oily material.

Workup

  1. temperatureThe mixture was refluxed for 5 hours
  2. customAfter returning to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried with magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1→hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-ad941fa6420f4f55b3314a7b4bfcd202
Source dataset
uspto-grants-2014_06
Patent number
US08741943B2

Reaction notes

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