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

HRID 347905

反応式

HRID 347905 の反応式
[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

参加物

7

反応物 4

HCID 1049PyridineHCID 8471TriethylamineHCID 92264-AzaindoleHCID 66827Phenylboronic Acid

生成物 1

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

試薬・触媒・溶媒 2

HCID 8895Cupric acetate触媒HCID 6344Dichloromethane溶媒2 回

実験手順

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)+.

後処理

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-2f4441f43afe4a7a8bcb4cfbf57ac8f6
出典データセット
uspto-grants-2007_02
特許番号
US07176215B2

関連ノート

読み込み中…