Phenylacetylene → HCID 53629126, compound

HRID 1926800Notes

Reaction equation

HRID 1926800 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([CH3:21])[C:10]=2[CH2:11][N:12]2[CH2:16][CH:15]([CH2:17][CH2:18][CH3:19])[CH2:14][C:13]2=[O:20])[CH:7]=1.[C:22]1([C:28]#[CH:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O.C(O)(C)C.[Pd]>[CH3:21][C:9]1[C:10]([CH2:11][N:12]2[CH2:16][CH:15]([CH2:17][CH2:18][CH3:19])[CH2:14][C:13]2=[O:20])=[C:5]2[N:4]=[CH:3][C:2]([C:29]#[C:28][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:7][N:6]2[N:8]=1

Participants

7

Reactant 3

HCID 10821PhenylacetyleneHCID 62657Potassium Phosphate, TribasicHCID 57743088HCID 57743088, compound

Product 1

HCID 53629126HCID 53629126, compoundYield 11%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolvent2×HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1-[(6-bromo-2-methylpyrazolo[1,5-a]pyrimidin-3-yl)methyl]-4-propylpyrrolidin-2-one 184 (0.66 mmol, 1 eq, 0.26 g) in 2 ml of water and 2 ml of isopropyl alcohol are added successively palladium on activated carbon (10%, 0.284 mmol, 0.5 eq, 30 mg), phenyl acetylene (0.68 mmol, 1.2 eq, 70 mg), and K3PO4 (1.13 mmol, 2 eq, 0.24 g) dissolved in 2 ml of water. The mixture is degassed and stirred vigorously overnight at 100° C. The solvent is removed under reduce pressure. The crude product is purified by chromatography on silicagel (AcOEt/hexane: 4/6) to afford 25 mg of 1-{[2-methyl-6-(phenylethynyl)pyrazolo[1,5-a]pyrimidin-3-yl]methyl}-4-propylpyrrolidin-2-one 199.

Workup

  1. customThe mixture is degassed
  2. customThe solvent is removed
  3. customThe crude product is purified by chromatography on silicagel (AcOEt/hexane: 4/6)

Sources & evidence

ORD record
ord-853686015e9f48d3be4a1731a5d585d7
Source dataset
uspto-grants-2012_05
Patent number
US08183241B2

Reaction notes

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