Water → HCID 18333094, compound

HRID 2269753Notes

Reaction equation

HRID 2269753 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[C:7]1([CH3:17])[CH:12]=[CH:11][C:10]([S:13]([OH:16])(=[O:15])=[O:14])=[CH:9][CH:8]=1.Br[C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27]([N:29]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH2:32][CH:31]([CH2:39][N:40]([CH3:42])[CH3:41])[CH2:30]2)=[O:28])=[CH:21][CH:20]=1.C(B(CC)[C:46]1[CH:47]=[N:48][CH:49]=[CH:50][CH:51]=1)C.O>C1(C)C=CC=CC=1.C(O)C.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>[C:7]1([CH3:17])[CH:8]=[CH:9][C:10]([S:13]([OH:16])(=[O:14])=[O:15])=[CH:11][CH:12]=1.[CH3:41][N:40]([CH2:39][CH:31]1[CH2:32][C:33]2[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:29]([C:27](=[O:28])[CH2:26][CH2:25][C:22]2[CH:23]=[CH:24][C:19]([C:46]3[CH:47]=[N:48][CH:49]=[CH:50][CH:51]=3)=[CH:20][CH:21]=2)[CH2:30]1)[CH3:42]

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 6428513-(Diethylboryl)pyridineHCID 18332993HCID 18332993, compound

Product 1

HCID 18333094HCID 18333094, compoundYield 62.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

2M Aqueous sodium carbonate solution (1.25 ml) was added to a suspension of 1-[3-(4-bromophenyl)propanoyl]-3-(N,N-dimethylamino)methyl-1,2,3,4-tetrahydroquinoline p-toluenesulfonate (400 mg) in toluene (10 ml) and ethanol (1.25 ml), which was stirred at room temperature for 10 minutes. Diethyl(3-pyridyl)borane (154 mg) and tetrakis(triphenylphosphine)palladium (24 mg) were added to the reaction mixture, which was heated under reflux under an argon atmosphere for 14 hours. Water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, then dried and concentrated. The residue was purified by alumina column chromatography (eluent: hexane/ethyl acetate=10/1 to 2/1), which was converted into its p-toluenesulfonate. The mixture was recrystallized from ethanol-IPE to give the entitled compound (250 mg).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux under an argon atmosphere for 14 hours
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by alumina column chromatography (eluent: hexane/ethyl acetate=10/1 to 2/1), which
  8. customThe mixture was recrystallized from ethanol-IPE

Sources & evidence

ORD record
ord-dc98a9d46f494f219f7602f1e152277d
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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