Pyridine → 4,6-Bis(4-fluorophenyl)-1-(4-methylsulfanylphenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridine

HRID 42580

反応式

HRID 42580 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)=[C:12]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[N:11]=[C:10]3[NH:27][N:28]=[CH:29][C:9]=23)=[CH:4][CH:3]=1.[CH3:30][S:31][C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1.N1C=CC=CC=1.C(N(CC)CC)C>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[C:10](=[N:27][N:28]([C:35]4[CH:36]=[CH:37][C:32]([S:31][CH3:30])=[CH:33][CH:34]=4)[CH:29]=3)[N:11]=[C:12]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[C:13]=2[C:14]2[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=2)=[CH:4][CH:3]=1.[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]3[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=3)=[C:12]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[N:11]=[C:10]3[N:27]([C:35]4[CH:36]=[CH:37][C:32]([S:31][CH3:30])=[CH:33][CH:34]=4)[N:28]=[CH:29][C:9]=23)=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 1049PyridineHCID 8471TriethylamineHCID 27339594-(Methylthio)phenylboronic acidHCID 119613744,6-Bis(4-fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine

生成物 2

HCID 670148224,6-Bis(4-fluorophenyl)-1-(4-methylsulfanylphenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridine収率 23%HCID 684441364,6-Bis(4-fluorophenyl)-2-(4-methylsulfanylphenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridine収率 10%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

In a volumetric flask molecular sieves of 4 Å (1 g, previously dried for 3 h at 200° C. under vacuum), 4,6-bis(4-fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine (0.30 g, 0.8 mmol, obtained in example 1), (4-methylsulfanylphenyl)boronic acid (0.26 g, 1.6 mmol), copper II acetate (0.28 g, 1.6 mmol), pyridine (0.12 g, 1.6 mmol), triethylamine (0.16 g, 1.6 mmol) and CH2Cl2 (22 mL) were introduced under argon atmosphere. This was stirred at room temperature for 2 days. It was filtered through celite and concentrated. The crude product obtained was purified by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford 40 mg of 4,6-bis(4-fluorophenyl)-2-(4-methylsulfanylphenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridine (yield: 10%) and 90 mg of 4,6-bis(4-fluorophenyl)-1-(4-methylsulfanylphenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridine (yield: 23%).

後処理

  1. additionwere introduced under argon atmosphere
  2. filtrationIt was filtered through celite
  3. concentrationconcentrated
  4. customThe crude product obtained
  5. customwas purified by chromatography on silica gel
  6. temperatureof increasing polarity as eluent

出典と根拠

ORDレコード
ord-d99890f47d5d43eab8fc0c59813c0349
出典データセット
uspto-grants-2013_09
特許番号
US08536194B2

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