Benzo(B)Thiophene-2-Boronic Acid → HCID 86757407, compound

HRID 1596757Notes

Reaction equation

HRID 1596757 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].[CH2:19]([N:26]1[CH2:34][C:33]2([C:35]([O:37][CH3:38])=[O:36])[CH:28]([C:29](I)=[CH:30][CH2:31][CH:32]2[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CO.COCCOC.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>[CH2:19]([N:26]1[CH2:34][C:33]2([C:35]([O:37][CH3:38])=[O:36])[CH:28]([C:29]([C:2]3[S:1][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[CH:3]=3)=[CH:30][CH2:31][CH:32]2[C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:27]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 3

HCID 2359Benzo(B)Thiophene-2-Boronic AcidHCID 10340Sodium CarbonateHCID 86755053HCID 86755053, compound

Product 1

HCID 86757407HCID 86757407, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 9.3 g (17.3 mmol) of benzothiophene-2-boronic acid trimeric anhydride in 100 cm3 of methanol and 400 cm3 of a 2N aqueous sodium carbonate solution are successively added to a solution of 22.36 g (47 mmol) of the levorotatory enantiomer of methyl (3aRS,4SR,7aRS)-2-benzyl-7-iodo-4-phenyl-1,2,3,4,5,7a-hexahydroisoindole-3a-carboxylate and of 6.03 g (5.2 mmol) of tetrakis(triphenylphosphine)palladium in 250 cm3 of 1,2-dimethoxyethane, the reaction mixture is then brought to reflux for two hours and stirring is maintained overnight at room temperature. After returning to a temperature in the region of 20° C., the reaction mixture is extracted with 800 cm3 of ethyl acetate and then the organic phase is washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The brown residue obtained is purified by flash chromatography on silica gel (230-400 mesh), elution being carried out with a cyclohexane/ethyl acetate (80/20 by volume) mixture. 11.04 g (50%) of the levorotatory enantiomer of methyl (3aRS,4SR,7aRS)-2-benzyl-4-phenyl-7-(2-benzothienyl)-1,2,3,4,5,7a-hexahydroisoindole-3a-carboxylate are thus obtained in the form of a yellow foam, the characteristics of which are as follows:

Workup

  1. temperatureto reflux for two hours
  2. customAfter returning to a temperature in the region of 20° C.
  3. extractionthe reaction mixture is extracted with 800 cm3 of ethyl acetate
  4. washthe organic phase is washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe brown residue obtained
  8. customis purified by flash chromatography on silica gel (230-400 mesh), elution

Sources & evidence

ORD record
ord-35d929659cf848a8ae48684087f1d270
Source dataset
uspto-grants-2001_09
Patent number
US06291679B1

Reaction notes

Loading…