Sodium Carbonate → HCID 178434368, compound

HRID 1774963Notes

Reaction equation

HRID 1774963 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([CH3:11])=[N:9][NH:8][C:5]2=[CH:6][N:7]=1.C([O-])([O-])=O.[Na+].[Na+].[NH:18]1[CH:22]=[C:21](B(O)O)[CH:20]=[N:19]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]>[CH3:11][C:10]1[C:4]2[C:5](=[CH:6][N:7]=[C:2]([C:21]3[CH:22]=[N:18][NH:19][CH:20]=3)[CH:3]=2)[NH:8][N:9]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 177502781H-Pyrazole-4-boronic acidHCID 178434364HCID 178434364, compound

Product 1

HCID 178434368HCID 178434368, compoundYield 15.1%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
150 °C

Procedure

To a solution of 5-bromo-3-methyl-1H-pyrazolo[3,4-c]pyridine (106 mg, 0.5 mmol) in DMF (5 mL) was added Pd(dppf)Cl2 (20 mg), saturated solution of Na2CO3 (1 mL) and 1H-pyrazol-4-ylboronic acid (67 mg, 0.6 mmol). Under argon, the mixture was stirred under microwave irradiation for 1 h at 150° 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 102 (15 mg, 15%). 1H NMR (500 MHz, MeOD) δ 8.88 (s, 1H), 8.16 (m, 2H), 8.00 (s, 1H), 2.61 (s, 3H); ESI MS m/z=200.1 (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-80566cbdb93246e19cab39b65a287671
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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