Potassium Carbonate → Methyl 3-[4-(2-butoxyethoxy)phenyl]-10-propyl-7,8,9,10-tetrahydropyrido[2,3-b]azocine-6-carboxylate

HRID 1182364Notes

Reaction equation

HRID 1182364 reaction equation
Br[C:2]1[CH:20]=[N:19][C:5]2[N:6]([CH2:16][CH2:17][CH3:18])[CH2:7][CH2:8][CH2:9][C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:11][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(=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:30]=[CH:31][C:32]([C:2]2[CH:20]=[N:19][C:5]3[N:6]([CH2:16][CH2:17][CH3:18])[CH2:7][CH2:8][CH2:9][C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:11][C:4]=3[CH:3]=2)=[CH:33][CH:34]=1)[CH2:22][CH2:23][CH3:24]

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 230910874-(2-Butoxyethoxy)phenylboric acidHCID 69425413Methyl 3-bromo-10-propyl-7,8,9,10-tetrahydropyrido[2,3-b]azocine-6-carboxylate

Product 1

HCID 69428219Methyl 3-[4-(2-butoxyethoxy)phenyl]-10-propyl-7,8,9,10-tetrahydropyrido[2,3-b]azocine-6-carboxylateYield 79.5%

Reagents, catalysts & solvents 4

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

Conditions

Temperature
115 °C

Procedure

A suspension of methyl 3-bromo-10-propyl-7,8,9,10-tetrahydropyrido[2,3-b]azocine-6-carboxylate (820 mg), 4-(2-butoxyethoxy)phenylboric acid (748 mg) and potassium carbonate (868 mg) in toluene (15 ml), ethanol (1.5 ml) and water (1.5 ml) was stirred under an argon atmosphere for 30 minutes. Tetrakis(triphenylphosphine)palladium (140 mg) was added thereto, and the mixture was heated at 115° C. for 6 hours under an argon atmosphere, which was allowed to cool. Water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over 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=4:1) to give methyl 3-[4-(2-butoxyethoxy)phenyl]-10-propyl-7,8,9,10-tetrahydropyrido[2,3-b]azocine-6-carboxylate (870 mg) as a yellow oily material.

Workup

  1. temperatureto cool
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1→hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-9537d88f4b534d82a57d918fae6bf284
Source dataset
uspto-grants-2007_10
Patent number
US07288654B2

Reaction notes

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