Ethanol → HCID 11310424, compound

HRID 646702Notes

Reaction equation

HRID 646702 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1B(O)O.C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.[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>[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 5206955-Bromo-1-indanoneHCID 27339602-Thiopheneboronic acid

Product 1

HCID 11310424HCID 11310424, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
115 °C

Procedure

To a solution of 5-bromo-1-indanone (0.52g, 2.5 mmol) in toluene (5 mL) were added tetrakis(triphenylphosphine)-palladium(0) (29 mg, 0.03 mmol), thiophene-2-boronic acid (0.48 g, 3.7 mmol), ethanol (5 mL), and 2.0 N sodium carbonate (3 mL). The solution was flushed with nitrogen for 3 minutes. The reaction was heated at 110-120° C. for 4 h. Reaction cooled to room temperature and diluted with ethyl acetate (200 mL). The organic layer was washed with saturated aqueous sodium bicarbonate (2×50 mL), water (40 mL), saturated aqueous sodium chloride (50 mL), dried over magnesium sulfate, filtered and concentrated to afford 5-(2-thienyl)-2,3-dihydro-1H-inden-1-one (0.50g, 94% yield) as pure solid product. 1H NMR (400 MHz, CDCl3) 7.80 (d, 1H), 7.70 (s, 1H), 7.62 (d, 1H), 7.43 (dd, 1H), 7.38 (dd, 1H), 7.12 (m, 1H), 3.20 (m, 2H), 2.66 (m, 2H).

Workup

  1. customThe solution was flushed with nitrogen for 3 minutes
  2. customReaction
  3. temperaturecooled to room temperature
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate (2×50 mL), water (40 mL), saturated aqueous sodium chloride (50 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-65228491f8da49988c252adc7b527faa
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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