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

HRID 347905

반응식

HRID 347905 반응식
[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

참가 물질

7

반응물 4

HCID 1049PyridineHCID 8471TriethylamineHCID 92264-AzaindoleHCID 66827Phenylboronic Acid

생성물 1

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

시약·촉매·용매 2

HCID 8895Cupric acetate촉매HCID 6344Dichloromethane용매2회

실험 절차

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)+.

후처리

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-2f4441f43afe4a7a8bcb4cfbf57ac8f6
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07176215B2

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