Water → HCID 71254021, compound

HRID 1774965Notes

Reaction equation

HRID 1774965 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([CH3:11])=[N:9][N:8]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[C:5]2=[CH:6][N:7]=1.[N:18]1[CH:23]=[C:22](B(O)O)[CH:21]=[N:20][CH:19]=1.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>[CH3:11][C:10]1[C:4]2[C:5](=[CH:6][N:7]=[C:2]([C:19]3[N:20]=[CH:21][CH:22]=[CH:23][N:18]=3)[CH:3]=2)[N:8]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)[N:9]=1

Participants

8

Reactant 4

HCID 962Water2×HCID 517044Potassium AcetateHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 86676683HCID 86676683, compound

Product 1

HCID 71254021HCID 71254021, compoundYield 95.45%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6342AcetonitrileSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
130 °C

Procedure

In a microwave reaction vials was charged with 5-bromo-3-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine (296 mg, 1.0 mmol), Pyrimidine-5-boronic acid (185 mg, 1.5 mmol), 1,1′-Bis(diphenylphosphino)ferrocenepalladium (II) chloride (81.7 mg, 0.1 mmol), 1.00 M of Potassium acetate in Water (1.5 mL, 1.5 mmol), 1.00 M of Sodium carbonate in Water (1.5 mL, 1.5 mmol), and Acetonitrile (10 mL). The reaction mixture was heated under microwave at 130° C. for 30 minutes. The mixture was concentrated and the residue was purified on silica eluted with 0 to 5% MeOH in DCM with 1% NH4OH to afford 3-methyl-5-(pyrimidin-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine (281.9 mg, 95.45%).

Workup

  1. customIn a microwave reaction vials
  2. concentrationThe mixture was concentrated
  3. customthe residue was purified on silica
  4. washeluted with 0 to 5% MeOH in DCM with 1% NH4OH

Sources & evidence

ORD record
ord-2547ac0dfaa14b97ba200acc5c5dffca
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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