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

HRID 1774966Notes

Reaction equation

HRID 1774966 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)[NH:4][N:3]=1.C([O-])([O-])=O.[Na+].[Na+].[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>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]>[C:23]1([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)[NH:4][N:3]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 178506572HCID 178506572, compound

Product 1

HCID 712536843-phenyl-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridineYield 60.2%

Reagents, catalysts & solvents 2

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

Procedure

To a solution of 3-iodo-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine from Example 4 (161 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 phenylboronic acid (74 mg, 0.6 mmol). The mixture was heated in argon under microwave radiation at 135 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 116 (82 mg, 60%). 1H NMR (400 MHz, DMSO) δ 9.33 (s, 1H), 9.21 (s, 1H), 8.56 (s, 1H), 8.53-8.51 (m, 2H), 8.12-8.10 (m, 2H), 7.57-7.44 (m, 4H). ESI MS m/z=273.7 (M+1

Workup

  1. temperatureThe mixture was heated in argon under microwave radiation at 135 for 60 min
  2. temperatureAfter cooling down
  3. customthe solvent was removed under reduced pressure
  4. customthe residue was purified by silica-gel column chromatography (mobile phase: EA:PE=1:1)

Sources & evidence

ORD record
ord-3fbda996044a4306acc6c59dc859868e
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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