Triethylamine → HCID 59595889, compound

HRID 2075139Notes

Reaction equation

HRID 2075139 reaction equation
[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11](B(O)O)=[CH:10][C:9]=2[CH:16]=1)[CH:2]([CH3:4])[CH3:3].Br[C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=1.C(N(CC)CC)C>C(O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([C:18]3[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=3)=[CH:10][C:9]=2[CH:16]=1)[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 707414-BromobenzaldehydeHCID 59595878HCID 59595878, compound

Product 1

HCID 59595889HCID 59595889, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5-isobutylbenzofuran-2-ylboronic acid (70 mg, 0.33 mmol), 4-bromobenzaldehyde (61 mg, 0.33 mmol), triethylamine (1.7 mL, 12.6 mmol) and bis(triphenylphosphine)palladium(II) chloride (12 mg, 0.017 mmol) in ethanol (10 mL) was irradiated in a microwave instrument at 100° C. for 20 min. The reaction mixture was cooled, and the solvent was removed. The residue was treated with water and extracted with ethyl acetate. The organic layer was dried and concentrated in vacuo (the aqueous work-up is optional). Purification by silica gel chromatography on ISCO system gave the title compound (59 mg, 65% yield): >99% purity by LCMS, ESI-MS: 279.2 (M+H)+.

Workup

  1. customwas irradiated in a microwave instrument at 100° C. for 20 min
  2. temperatureThe reaction mixture was cooled
  3. customthe solvent was removed
  4. additionThe residue was treated with water
  5. extractionextracted with ethyl acetate
  6. customThe organic layer was dried
  7. concentrationconcentrated in vacuo (the aqueous work-up
  8. customPurification by silica gel chromatography on ISCO system

Sources & evidence

ORD record
ord-4c98a0cbe70041adb0a75d69229c9442
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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