Water → HCID 178420767, compound

HRID 1775026Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:15]=[CH:14][NH:13][N:12]=3)=[N:9][N:8]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][O:17]3)[C:5]2=[CH:6][N:7]=1.[N:22]1[CH:27]=[CH:26][CH:25]=[C:24](B(O)O)[CH:23]=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>[NH:13]1[CH:14]=[CH:15][C:11]([C:10]2[C:4]3[C:5](=[CH:6][N:7]=[C:2]([C:24]4[CH:23]=[N:22][CH:27]=[CH:26][CH:25]=4)[CH:3]=3)[N:8]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][O:17]3)[N:9]=2)=[N:12]1

Participants

Conditions

Temperature: 130 °C

Procedure

A microwave reaction vials was charged with 5-bromo-3-(1H-pyrazol-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine as an off-white solid (153.7 mg 0.44 mmol), 3-Pyridylboronic acid (81.62 mg, 0.66 mmol), 1,1′-Bis(diphenylphosphino)ferrocenepalladium (II) chloride (36.15 mg, 0.044 mmol), 1.00 M of Potassium acetate in Water (0.66 mL, 0.66 mmol), 1.00 M of Sodium carbonate in Water (0.66 mL, 0.66 mmol), and Acetonitrile (3 mL). The reaction mixture was heated under microwave at 130° C. for 20 minutes The mixture was concentrated and the residue was purified on silica eluted with 0 to 7% MeOH in DCM with 1% NH4OH to afford 3-(1H-pyrazol-3-yl)-5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine (73.4 mg, 48%).

Workup

customA microwave reaction vials
concentrationwas concentrated
customthe residue was purified on silica
washeluted with 0 to 7% MeOH in DCM with 1% NH4OH

Sources & evidence

ORD record: ord-d50222be99a242bdb982db0bae4f083c
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260425B2

Reaction notes

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