Ethyl Acetate → 5-(Furan-3-yl)pyridine-3-carbaldehyde

HRID 479253Notes

Reaction equation

HRID 479253 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:8]=[O:9])[CH:7]=1.S1C=CC(B(O)O)=C1.C(=O)([O-])[O-].[Na+].[Na+].[C:24]([O:27][CH2:28][CH3:29])(=O)[CH3:25]>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.O>[O:27]1[CH:28]=[CH:29][C:25]([C:2]2[CH:7]=[C:6]([CH:8]=[O:9])[CH:5]=[N:4][CH:3]=2)=[CH:24]1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 581760Thiophene-3-boronic acidHCID 27847345-Bromo-3-pyridinecarboxaldehyde

Product 1

HCID 180024175-(Furan-3-yl)pyridine-3-carbaldehyde

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 3-Bromo-5-pyridinecarboxaldehyde from Example 59 Step D (200 mg, 1.08 mmol) and tetrakis(triphenylphosphine)palladium(0) (70 mg, 0.06 mmol) in DME (5 mL) was stirred at room temperature for 5 minutes. Thiophene-3-boronic acid (141 mg, 1.08 mmol) was added and the stirring was continued for 10 more minutes. Then, sodium carbonate solution (2 M, 5 mL) was added and the reaction mixture was heated to refluxed for 12 hours. After it was cooled to room temperature, the reaction mixture was distributed between ethyl acetate (50 mL) and water (50 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated, and purified on preparative TLC (2000 microns, hexanes/ethyl acetate=1/1) to get 5-(3-furanyl)-3-pyridinecarboxaldehyde as a pale solid. 1H NMR (CDCl3, 300 MHz): δ10.18 (s, 1 H), 9.11 (d, J=2.1 Hz, 1 H), 8.98 (d, J=1.8 Hz, 1 H), 8.33 (t, J=2.1 Hz, 1 H), 7.44 (dd, J=1.2, 1.5 Hz, 1 H), 7.44-7.52 (m, 2 H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto refluxed for 12 hours
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. custompurified on preparative TLC (2000 microns, hexanes/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-db61abe5fd4840b38ea4619c89df3c16
Source dataset
uspto-grants-2003_11
Patent number
US06642237B1

Reaction notes

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