Sodium Carbonate → 5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine

HRID 1774958Notes

Reaction equation

HRID 1774958 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+].[N:17]1[CH:22]=[CH:21][CH:20]=[C:19](B(O)O)[CH:18]=1>CN(C=O)C.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:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:2]2[CH:3]=[C:4]3[CH:10]=[N:9][NH:8][C:5]3=[CH:6][N:7]=2)[CH:18]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 457897785-Bromo-1H-pyrazolo[3,4-c]pyridine

Product 1

HCID 866766805-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridineYield 60.1%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-bromo-1H-pyrazolo[3,4-c]pyridine from Example 6 (100 mg, 0.5 mmol) in DMF (5 mL) was added Pd(dppf)Cl2 (20 mg), saturated solution of Na2CO3 (1 mL) and pyridin-3-ylboronic acid (74 mg, 0.6 mmol). The mixture was stirred under argon for 16 h at 80° C. 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-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine (59 mg, 60%). 1H NMR (500 MHz, MeOD) δ 9.17 (s, 1H), 9.09 (s, 1H), 8.52 (d, J=3.5, 1H), 8.44 (q, J=7, 2, 1H), 8.29 (d, J=5, 1H), 8.23 (s, 1H), 7.53 (q, J=9.5, 5.5, 1H). ESI MS m/z=197.1 (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-29e0100c35e440a7a550250bf2f2d281
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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