Bromine → HCID 23114120, compound

HRID 2376514Notes

Reaction equation

HRID 2376514 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[C:14]3[C:15]([CH3:28])=[C:16]([NH:20][C:21](=[O:27])[CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:17]([CH3:19])=[CH:18][C:13]=3S[CH2:11]2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[Br:29]Br.C(=O)([O-])O.[Na+].ClC1C=CC=C(C(OO)=O)C=1.[S:47]([O-:51])(O)(=O)=[O:48].[Na+]>ClCCl.[Fe].O>[Br:29][C:18]1[C:13]2[S:47](=[O:51])(=[O:48])[CH2:11][CH:10]([C:7]3[CH:6]=[CH:5][C:4]([CH:1]([CH3:2])[CH3:3])=[CH:9][CH:8]=3)[C:14]=2[C:15]([CH3:28])=[C:16]([NH:20][C:21](=[O:27])[CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:17]=1[CH3:19]

Participants

9

Reactant 5

HCID 24408BromineHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 516919Sodium BisulfateHCID 23114340HCID 23114340, compound

Product 1

HCID 23114120HCID 23114120, compoundYield 55%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of N-(3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzothien-5-yl)-3,3-dimethylbutanamide (560 mg, 1.41 mmol) obtained in Example 161 and iron powder (5.2 mg, 0.094 mmol) in dichloromethane (10 mL) was added bromine (225 mg, 1.41 mmol) at 0° C. and the resulting mixture was stirred at the same temperature for 1 hour. Water was poured into the reaction mixture and the product was extracted with ethyl acetate. The extracts were washed with an aqueous sodium hydrogen carbonate solution and water, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. To a mixture of the obtained residue and sodium hydrogen carbonate (150 mg, 1.79 mmol) in dichloromethane (5 mL) was added m-chloroperbenzoic acid (161 mg, 1.01 mmol) at 0° C. and the resulting mixture was stirred at room temperature for 1 hour. To the reaction solution was added an aqueous sodium hydrogensulfate solution, the organic layer was separated, and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane ethyl acetate=3:1) to obtain 393 mg (yield: 55%) of the title compound. Melting point: 211-213° C. (hexane-ethyl acetate).

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe extracts were washed with an aqueous sodium hydrogen carbonate solution and water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. stirringthe resulting mixture was stirred at room temperature for 1 hour
  7. customthe organic layer was separated
  8. extractionthe aqueous layer was extracted with dichloromethane
  9. washThe combined organic layers were washed with water and saturated brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customThe obtained residue was purified by silica gel column chromatography (hexane ethyl acetate=3:1)

Sources & evidence

ORD record
ord-a09c49a6271e4bda84384680a0d526d2
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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