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Water → 3-(6-fluoro-5-methylpyridin-2-yl)-5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridine

HRID 1775075
Notes
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Reaction equation

HRID 1775075 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([C:9]2[C:17]3[C:12](=[CH:13][N:14]=[C:15]([C:18]4[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=4)[CH:16]=3)[N:11]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[N:10]=2)=[N:6][C:7]=1[F:8].[CH3:32]B(O)O.C([O-])(=O)C.[K+].O>C(=O)([O-])[O-].[Na+].[Na+].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].C(#N)C>[F:8][C:7]1[N:6]=[C:5]([C:9]2[C:17]3[C:12](=[CH:13][N:14]=[C:15]([C:18]4[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=4)[CH:16]=3)[N:11]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[N:10]=2)[CH:4]=[CH:3][C:2]=1[CH3:32]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 962Water2×HCID 139377Methylboronic Acid2×HCID 517044Potassium AcetateHCID 71253589HCID 71253589, compound

Product 1

HCID 712536643-(6-fluoro-5-methylpyridin-2-yl)-5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridineYield 84.3%

Reagents, catalysts & solvents

3
HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6342AcetonitrileSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
150 °C

Procedure

A microwave reaction vial was charged with 3-(5-chloro-6-fluoropyridin-2-yl)-5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridine (387.1 mg, 0.8489 mmol), methyl boronic acid (254.1 mg, 4.245 mmol), 1,1′-Bis(diphenylphosphino)ferrocenepalladium (II) chloride (69.3 mg, 0.085 mmol), 1.00 M of Potassium acetate in Water (1.27 mL, 1.27 mmol), 1.00 M of Sodium carbonate in Water (1.27 mL, 1.27 mmol), and Acetonitrile (10 mL). The reaction mixture was heated under microwave at 150° C. for 5 minutes. Added another 5 equivalences of Methyl boronic acid and continue heated under microwave at 150° C. for 3 minutes. The same procedure was repeated one more times. The mixture was concentrated, and the residue was purified on silica eluted with 0 to 100% EtOAc in Heptane to afford 3-(6-fluoro-5-methylpyridin-2-yl)-5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridine (311.7 mg, 84%).

Workup

  1. customA microwave reaction
  2. temperaturecontinue heated under microwave at 150° C. for 3 minutes
  3. concentrationThe mixture was concentrated
  4. customthe residue was purified on silica
  5. washeluted with 0 to 100% EtOAc in Heptane

Sources & evidence

ORD record
ord-99f4a865f7694f49b197fc96ac3511a1
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09260425B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes