Hydrochloric Acid → HCID 23431851, compound

HRID 2218335Notes

Reaction equation

HRID 2218335 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][C:10](=[O:12])[C:9]3[C:13]([O:19][CH3:20])=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:8]=3[O:7][C:6]=2[CH:21]=1.[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].Cl>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1>[C:22]1([C:2]2[CH:3]=[CH:4][C:5]3[CH2:11][C:10](=[O:12])[C:9]4[C:13]([O:19][CH3:20])=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:8]=4[O:7][C:6]=3[CH:21]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 234318553-Iodo-7,9-dimethoxy-10,11-dihydrodibenz[b,f]oxepin-10-one

Product 1

HCID 23431851HCID 23431851, compoundYield 31.2%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
125 °C

Procedure

To 3-iodo-7,9-dimethoxy-10,11-dihydrodibenz[b,f]oxepin-10-one (52) (403 mg, 1.0 mmol), phenyl boronic acid (186 mg, 1.5 mmol), a 2M potassium carbonate aqueous solution (0.6 mL, 1.2 mmol) and tetrakis(triphenylphosphine) palladium (118 mg, 0.10 mmol) was added 5 mL of toluene and stirred at 125° C. for 19 hours. After completion of the reaction, the reaction solution was neutralized with dilute hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and then with a saturated sodium chloride aqueous solution and dried with anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent; hexane:ethyl acetate=2:1) to obtain 108 mg (yield 31%) of 3-phenyl-7,9-dimethoxy-10,11-dihydrodibenz[b,f]oxepin-10-one. Demethylation reaction was carried out according to the method of Example 1 to obtain the title compound.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialwith a saturated sodium chloride aqueous solution and dried with anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (developing solvent; hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-b3cbfc37a3904aa3993e85888c290384
Source dataset
uspto-grants-2008_08
Patent number
US07410997B2

Reaction notes

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