Pyridine → 1-Phenyl-1H-pyrrolo[3,2-b]pyridine

HRID 347905Notes

Reaction equation

HRID 347905 reaction equation
[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C.N1C=CC=CC=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:10]1([N:1]2[C:9]3[C:4](=[N:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 92264-AzaindoleHCID 66827Phenylboronic Acid

Product 1

HCID 210839631-Phenyl-1H-pyrrolo[3,2-b]pyridineYield 39.5%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

1H-Pyrrolo[3,2-b]pyridine (0.5 g, 4.24 mmol), phenylboronic acid (1.03 g, 8.44 mmol), copper(II) acetate (1.54 g, 8.48 mmol), and 4A molecular sieves (2 g), were suspended in DCM (10 mL). Triethylamine (1.19 mL, 8.5 mmol) and pyridine (0.7 mL, 8.65 mmol) were added and the reaction stirred at r.t. for three days. The reaction mixture was diluted with further DCM, filtered and concentrated in vacuo. Chromatography (silica, EtOAc) gave the title compound (325 mg). δH (CDCl3) 7.80 (1H, d, J 8.2 Hz), 7.54–7.30 (7H, m), 7.15 (1H, brs), 6.88 (1H, brs). LCMS (ES+) RT 1.20 minutes, 195 (M+H)+.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2f4441f43afe4a7a8bcb4cfbf57ac8f6
Source dataset
uspto-grants-2007_02
Patent number
US07176215B2

Reaction notes

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