Sodium Carbonate → HCID 86676682, compound

HRID 1774957Notes

Reaction equation

HRID 1774957 reaction equation
Br[C:2]1[CH:3]=[C:4]2[CH:10]=[N:9][NH:8][C:5]2=[CH:6][N:7]=1.C([O-])([O-])=O.[Na+].[Na+].CC1(C)C(C)(C)OB([C:25]2[NH:29][N:28]=[CH:27][CH:26]=2)O1>COCCOC.CCO.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]>[NH:28]1[CH:27]=[C:26]([C:2]2[CH:3]=[C:4]3[CH:10]=[N:9][NH:8][C:5]3=[CH:6][N:7]=2)[CH:25]=[N:29]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 219315393-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 457897785-Bromo-1H-pyrazolo[3,4-c]pyridine

Product 1

HCID 86676682HCID 86676682, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 20074477Dimethoxyethane ethanolSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 5-bromo-1H-pyrazolo[3,4-c]pyridine (100 mg, 0.5 mmol) in DME:EtOH (5:1, 5 mL) was added Pd(dppf)Cl2 (20 mg), saturated solution of Na2CO3 (1 mL) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (116 mg, 0.6 mmol). Under argon the mixture was stirred under microwave irradiation at 150° C. for 60 min. After cooling down, the solvent was removed under reduced pressure and the residue was purified by silica-gel column chromatography (mobile phase: EA:PE=1:1) to afford 5-(1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridine (20 mg, 22%). 1H NMR (500 MHz, MeOD) δ 9.05 (s, 1H), 8.24 (m, 2H), 7.75 (s, 1H), 6.89 (s, 1H). ESI MS m/z=186.1 (M+1)

Workup

  1. temperatureAfter cooling down
  2. customthe solvent was removed under reduced pressure
  3. customthe residue was purified by silica-gel column chromatography (mobile phase: EA:PE=1:1)

Sources & evidence

ORD record
ord-d22b2f94047e47929e9f283a20f0c817
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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