Acetonitrile → HCID 71253874, compound

HRID 1775099Notes

Reaction equation

HRID 1775099 reaction equation
C([N:4]1[CH2:8][CH2:7][N:6]([C:9]2[C:17]3[C:12](=[CH:13][N:14]=[C:15](Br)[CH:16]=3)[N:11]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][O:20]3)[N:10]=2)[C:5]1=[O:25])(=O)C.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28](B(O)O)[CH:27]=1.C(#N)C.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]>[N:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:15]2[CH:16]=[C:17]3[C:9]([N:6]4[CH2:7][CH2:8][NH:4][C:5]4=[O:25])=[N:10][N:11]([CH:19]4[CH2:24][CH2:23][CH2:22][CH2:21][O:20]4)[C:12]3=[CH:13][N:14]=2)[CH:27]=1

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 517044Potassium AcetateHCID 27343783-Pyridinylboronic acidHCID 86676697HCID 86676697, compound

Product 1

HCID 71253874HCID 71253874, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent2×HCID 10340Sodium CarbonateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution containing 1-acetyl-3-(5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)imidazolidin-2-one (0.295 g, 0.722 mmol), 3-pyridineboronic acd pinacol ester (0.444 g, 2.17 mmol), 1,1′-Bis(diphenylphosphino)ferrocenepalladium (II) chloride (0.0472 g, 0.0578 mmol) in Acetonitrile (5.47 mL, 105 mmol) was added 1.00 M of Potassium acetate in Water (1.44 mL) and 1.00 M of Sodium carbonate in Water (1.44 mL). The reaction was stirred at 100° C. for 3 h. The reaction is filtered thru celite. The crude product was diluted in EtOAc then washed with water and sat. NaCl. The organic layer was dried Na2SO4, filtered, and concentrated to give 1-(5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)imidazolidin-2-one. ESI MS m/z=365.2 (M+1).

Workup

  1. filtrationThe reaction is filtered thru celite
  2. additionThe crude product was diluted in EtOAc
  3. washthen washed with water and sat. NaCl
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-156a9ac54d404cb4b7d3006f5d7f90d0
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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