Triethylamine → 3-(Benzofuran-5-yl)pyridine

HRID 2264545Notes

Reaction equation

HRID 2264545 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](B(O)O)[CH:2]=1.Br[C:11]1[CH:12]=[CH:13][C:14]2[O:18][CH:17]=[CH:16][C:15]=2[CH:19]=1.C(N(CC)CC)C>CCO>[O:18]1[C:14]2[CH:13]=[CH:12][C:11]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[CH:19][C:15]=2[CH:16]=[CH:17]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 90015Benzofuran, 5-bromo-HCID 27343783-Pyridinylboronic acid

Product 1

HCID 595959313-(Benzofuran-5-yl)pyridineYield 63.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5 pyridin-3-ylboronic acid (390 mg, 3.18 mmol), 5-bromobenzofuran (500 mg, 2.54 mmol), palladiumdichlorobis(triphenylphosphine) (111 mg, 0.16 mmol) and triethylamine (8.8 mL, 63.5 mmol) in EtOH was irradiated in the microwave at 100° C. for 1200 s. Removal of the solvents followed by dissolving in CH2Cl2 and filtering gave the residue after concentration of the solvent under reduced pressure. The compound was purified on ISCO to afford 316 mg of the title compound as a light yellow solid: 1H NMR (400 MHz, CDCl3) δ 8.89 (s, 1H), 8.60 (d, 1H), 7.90 (d, 1H), 7.80 (s, 1H), 7.69 (s, 1H), 7.55 (d, 1H), 7.50 (d, 1H) 7.38 (dd, 1H), 6.85 (dd, 1H). MS (ESI) m/z: Calculated: 195.07; Observed: 196.30 (M++1).

Workup

  1. customRemoval of the solvents
  2. dissolutionby dissolving in CH2Cl2
  3. filtrationfiltering
  4. customgave the residue after concentration of the solvent under reduced pressure
  5. customThe compound was purified on ISCO

Sources & evidence

ORD record
ord-3264a8f190534268bab2355028db24b3
Source dataset
uspto-grants-2010_12
Patent number
US07855193B2

Reaction notes

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