Sodium Carbonate → HCID 178434365, compound

HRID 1774967Notes

Reaction equation

HRID 1774967 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.[F:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1.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].O1CCOCC1>[F:12][C:13]1[CH:18]=[C:17]([C:2]2[CH:3]=[C:4]3[C:10]([CH3:11])=[N:9][NH:8][C:5]3=[CH:6][N:7]=2)[CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 178434364HCID 178434364, compound

Product 1

HCID 178434365HCID 178434365, compoundYield 34.8%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

Under nitrogen protection, to 6 mL of dioxane was added 5-bromo-3-methyl-1H-pyrazolo[3,4-c]pyridine from Example 102 (0.21 g, 1 mmol), 3-fluorophenylboronic acid (0.28 g, 2 mmol), PdCl2(dppf) (87 mg, 0.1 mmol) and 2 M Na2CO3 (2 mmol, 1 mL). The suspension was heated under microwave radiation at 130° C. for 1 hour. It was cooled to room temperature and the solvent was removed the solvent. The crude product was purified by SGC (EtOAc/Petroleum:1/1) to afford 79 mg (34%) of 122 as a white solid. 1H NMR (400 MHz, CDCl3): δ 9.12 (s, 1H), 7.98 (s, 1H), 7.75-7.82 (m, 2H), 7.44-7.47 (m, 1H), 7.08-7.09 (m, 1H), 2.67 (s, 3H). ESI MS m/z=229 (M+1)

Workup

  1. temperatureIt was cooled to room temperature
  2. customthe solvent was removed the solvent
  3. customThe crude product was purified by SGC (EtOAc/Petroleum:1/1)

Sources & evidence

ORD record
ord-6c72994cc3414574ad8be648aee04f8d
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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