Quinone → HCID 59323043, compound

HRID 2390046Notes

Reaction equation

HRID 2390046 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][CH:20]=[CH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:3]=1[CH2:4][NH:5][S:6]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])(=[O:8])=[O:7].C1(=O)C=CC(=O)C=C1.[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.C(OCC)C>[CH2:21]([C:20]1[N:5]([S:6]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])(=[O:7])=[O:8])[CH2:4][C:3]2[C:15]([CH:19]=1)=[CH:16][CH:17]=[CH:18][C:2]=2[F:1])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 4650QuinoneHCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 68518692HCID 68518692, compound

Product 1

HCID 59323043HCID 59323043, compoundYield 50.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere, 20 mg of N-(2-fluoro-6-cinnamylbenzyl)-2-methoxycarbonylethanesulfonamide, 3 mg of PdCl2(CH3CN)2, 6 mg of benzoquinone, 21 mg of lithium chloride, and 12 mg of sodium carbonate were dissolved in 1 mL of THF, followed by stirring under reflux for 36 hours. After completion of the reaction, to the reaction liquid was added diethyl ether, followed by filtration through Celite, and to the filtrate was added water, followed by extraction with diethyl ether. Then, the organic layer was washed with an aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue obtained was purified using PTLC (n-hexane:ethyl acetate=1:1) to obtain 10 mg (yield 46%) of a title compound as a yellow solid.

Workup

  1. temperatureunder reflux for 36 hours
  2. customAfter completion of the reaction
  3. customto the reaction liquid
  4. filtrationfollowed by filtration through Celite
  5. additionto the filtrate was added water
  6. extractionfollowed by extraction with diethyl ether
  7. washThen, the organic layer was washed with an aqueous sodium bicarbonate solution and saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue obtained
  11. customwas purified

Sources & evidence

ORD record
ord-9a598f05ff4b46c182ea58f5f2554276
Source dataset
uspto-grants-2012_09
Patent number
US08273766B2

Reaction notes

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