Sodium Carbonate → 3-(1-methyl-1H-indazol-5-yl)pyridin-2(1H)-one

HRID 879313Notes

Reaction equation

HRID 879313 reaction equation
Br[C:2]1[C:3]([OH:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:9][N:10]1[C:18]2[C:13](=[CH:14][C:15](B(O)O)=[CH:16][CH:17]=2)[CH:12]=[N:11]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.O.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:9][N:10]1[C:18]2[C:13](=[CH:14][C:15]([C:2]3[C:3](=[O:8])[NH:4][CH:5]=[CH:6][CH:7]=3)=[CH:16][CH:17]=2)[CH:12]=[N:11]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 225589101-Methyl-1H-indazole-5-boronic acidHCID 178517701HCID 178517701, compound

Product 1

HCID 866998333-(1-methyl-1H-indazol-5-yl)pyridin-2(1H)-one

Reagents, catalysts & solvents 3

HCID 178419050HCID 178419050, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

The suspension of 3-bromo-2-hydroxypyridine (80 mg, 0.46 mmol), 1-methyl-1H-indazol-5-ylboronic acid (121 mg, 0.69 mmol) and sodium carbonate (146 mg, 1.38 mmol) in DMF (2.0 mL) and H2O (0.4 mL) was degassed with N2 for 5 minutes. To the mixture was added bis(triphenylphosphine)palladium (II) dichloride (67 mg, 0.09 mmol), and the resulting mixture was heated at 90° C. for 2 h. The reaction mixture was filtered and purified by reverse phase HPLC (Gemini, 5 to 100% ACN/H2O+0.1% TFA) to give the product. LCMS-ESI+ (m/z): [M+H]+ calcd for C13H12N3O: 226.25; Found: 226.2.

Workup

  1. customwas degassed with N2 for 5 minutes
  2. filtrationThe reaction mixture was filtered
  3. custompurified by reverse phase HPLC (Gemini, 5 to 100% ACN/H2O+0.1% TFA)
  4. customto give the product

Sources & evidence

ORD record
ord-9853f38605c74d0283248f2192bb9de9
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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