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

HRID 42580
Notes
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Reaction equation

HRID 42580 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 2

HCID 670148224,6-Bis(4-fluorophenyl)-1-(4-methylsulfanylphenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridineYield 23%
HCID 68444136
4,6-Bis(4-fluorophenyl)-2-(4-methylsulfanylphenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridine
Yield 10%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-d99890f47d5d43eab8fc0c59813c0349
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08536194B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes