Sodium Carbonate → 5-Bromo-3-phenyl-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-pyrazolo[3,4-b]pyridine

HRID 1943870Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:10](I)=[N:9][N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:5]2=[N:6][CH:7]=1.[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([O-])([O-])=O.[Na+].[Na+].CCO.O>COC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:9][N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:5]2=[N:6][CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

PdCl2(dppf) dichloromethane adduct (0.017 g, 0.02 mmol) was added to a suspension of 5-bromo-3-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-b]pyridine (0.185 g, 0.41 mmol), phenylboronic acid (0.050 g, 0.41 mmol) and Na2CO3 (0.064 g, 0.61 mmol) in dimethylether (“DME”)/EtOH/H2O (5:2:1, 8 mL). The reaction mixture was purged with argon for 10 minutes and then heated to 90° C. under argon for 2 hours. The reaction mixture was cooled to room temperature and concentrated. The crude product was purified by column chromatography, eluting with hexanes/ethyl acetate (50:1) to give 5-bromo-3-phenyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-b]pyridine (0.080 g, 49%) as an oil.

Workup

customThe reaction mixture was purged with argon for 10 minutes
temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated
customThe crude product was purified by column chromatography
washeluting with hexanes/ethyl acetate (50:1)

Sources & evidence

ORD record: ord-f3dae0a4b7824c129ea0db4653a472bc
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394795B2

Reaction notes

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