Sodium Carbonate → HCID 86644413, compound

HRID 2194693Notes

Reaction equation

HRID 2194693 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]=O)[S:5][C:6]=1Br.[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1B(O)O.[C:20](=[O:23])([O-])[O-].[Na+].[Na+]>COCCOC.O.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>[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:3]1[CH:2]=[C:6]([CH:20]=[O:23])[S:5][C:4]=1[C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[F:10]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 8131644,5-Dibromothiophene-2-carbaldehydeHCID 27343542-Fluorophenylboronic acid

Product 1

HCID 86644413HCID 86644413, compoundYield 14%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 4,5-dibromothiophene-2-carbaldehyde (2.0 g), (2-fluorophenyl)boronic acid (1.6 g), tetrakis(triphenylphosphine)palladium (0) (855 mg) and sodium carbonate (2.0 g) in 1,2-dimethoxyethane (32 mL) and water (8 mL) was stirred at 80° C. for 6 hr under a nitrogen atmosphere. The reaction mixture was cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=99:1→9:1→17:3) to give the title compound as a colorless amorphous (yield 310 mg, yield 14%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=99:1→9:1→17:3)

Sources & evidence

ORD record
ord-8490dc657c274b36b0c91e3bb6ac5c8d
Source dataset
uspto-grants-2012_12
Patent number
US08334301B2

Reaction notes

Loading…