Dimethylacetamide → HCID 86630676, compound

HRID 1915567Notes

Reaction equation

HRID 1915567 reaction equation
Br[C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:8]([C:17]3[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=3)=[N:7][C:6]=12.C[C:26]([N:28](C)C)=O>O.ClCCl.[Zn].[C-]#N.[C-]#N.[Zn+2]>[CH:21]([C:20]1[CH:23]=[CH:24][C:17]([C:8]2[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:10][N:5]3[N:4]=[CH:3][C:2]([C:26]#[N:28])=[C:6]3[N:7]=2)=[CH:18][CH:19]=1)=[O:22]

Participants

7

Reactant 2

HCID 31374DimethylacetamideHCID 86630675HCID 86630675, compound

Product 1

HCID 86630676HCID 86630676, compound

Reagents, catalysts & solvents 4

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23994ZincCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
160 °C

Procedure

400 mg 4-(3-bromo-6-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzaldehyde (prepared as described under example 31), 7.0 mg zinc powder, 75.0 mg Zn(CN)2 and 39.0 mg dichloride[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct are suspended in 10 ml dimethylacetamide and the mixture is heated for 45 min under microwave irradiation to 160° C. The workup is performed by diluting the mixture with water and dichloromethane, extracting the aqueous layer twice and drying the combined organic layers over Na2SO4. The compound is isolated by evaporation of the solvent and chromatography on silica gel (dichloromethane/ethyl acetate).

Workup

  1. extractionextracting the aqueous layer twice
  2. dry with materialdrying the combined organic layers over Na2SO4
  3. customThe compound is isolated by evaporation of the solvent and chromatography on silica gel (dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-5e5a057e145249b986c3b26f6580c40a
Source dataset
uspto-grants-2013_12
Patent number
US08614218B2

Reaction notes

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