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

HRID 1775046Notes

Reaction equation

I[C:2]1[C:10]2[C:5](=[CH:6][N:7]=[C:8]([C:11]3[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=3)[CH:9]=2)[N:4]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[N:3]=1.[CH3:25][N:26]1[CH:30]=[CH:29][C:28](B2OC(C)(C)C(C)(C)O2)=[N:27]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>[CH3:25][N:26]1[CH:30]=[CH:29][C:28]([C:2]2[C:10]3[C:5](=[CH:6][N:7]=[C:8]([C:11]4[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=4)[CH:9]=3)[N:4]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[N:3]=2)=[N:27]1

Participants

Conditions

Temperature: 150 °C

Procedure

In a microwave reaction vials was charged with 3-iodo-5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridine (49.10 mg, 0.11 mmol), 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (33.19 mg, 0.16 mmol), 1,1′-Bis(diphenylphosphino)ferrocenepalladium (II) chloride (8.68 mg, 0.011 mmol), 1.00 M of Potassium acetate in Water (0.16 mL, 0.16 mmol), 1.00 M of Sodium carbonate in Water (0.16 mL, 0.16 mmol), and Acetonitrile (3 mL). The reaction mixture was heated under microwave at 150° C. for 5 minutes. The mixture was concentrated to afford 3-(1-methyl-1H-pyrazol-3-yl)-5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridine, which was used without purification.

Workup

customIn a microwave reaction vials
concentrationThe mixture was concentrated

Sources & evidence

ORD record: ord-728d8f15e0214e19836fcbb5a917897d
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260425B2

Reaction notes

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