Potassium Phosphate, Tribasic → HCID 66826683, compound

HRID 1912468Notes

Reaction equation

HRID 1912468 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:8]2([CH3:18])[NH:13][C:12](=[O:14])[CH2:11][N:10]3[N:15]=[CH:16][CH:17]=[C:9]23)[CH:5]=[CH:6][CH:7]=1.[CH3:19][O:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[N:25][CH:26]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.CCO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:19][O:20][C:21]1[CH:22]=[C:23]([C:2]2[CH:3]=[C:4]([C:8]3([CH3:18])[NH:13][C:12](=[O:14])[CH2:11][N:10]4[N:15]=[CH:16][CH:17]=[C:9]34)[CH:5]=[CH:6][CH:7]=2)[CH:24]=[N:25][CH:26]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 27630875-Methoxypyridine-3-boronic AcidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 66826768HCID 66826768, compound

Product 1

HCID 66826683HCID 66826683, compoundYield 51%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

Palladium(II) acetate (0.022 g, 0.097 mmol) was added to a stirred suspension of rac-4-(3-chloro-phenyl)-4-methyl-4,5-dihydro-pyrazolo[1,5-a]pyrazin-6-one (0.17 g, 0.65 mmol), 5-methoxypyridine-3-boronic acid (0.15 g, 0.97 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.080 g, 0.195 mmol) and potassium phosphate (0.28 g, 1.30 mmol) in toluene (2 mL) and EtOH (0.2 mL) at room temperature and under nitrogen. The mixture was stirred at 150° C. for 30 minutes under microwave irradiation. Then the mixture was filtered through diatomaceous earth and washed with AcOEt. The filtrate was evaporated in vacuo. The residue was purified by flash column chromatography (silica gel; AcOEt). The desired fractions were collected and concentrated in vacuo to yield rac-4-[3-(5-methoxy-pyridin-3-yl)-phenyl]-4-methyl-4,5-dihydro-pyrazolo[1,5-a]pyrazin-6-one (0.11 g, 51% yield) as a white solid.

Workup

  1. filtrationThen the mixture was filtered through diatomaceous earth
  2. washwashed with AcOEt
  3. customThe filtrate was evaporated in vacuo
  4. customThe residue was purified by flash column chromatography (silica gel; AcOEt)
  5. customThe desired fractions were collected
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-068e50b72fbc4c25a9a778cb60da7a59
Source dataset
uspto-grants-2013_12
Patent number
US08609660B2

Reaction notes

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