Dimethylacetamide → HCID 86630676, compound

HRID 1851202Notes

Reaction equation

HRID 1851202 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 above), 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 were suspended in 10 mL dimethylacetamide and the mixture was heated for 45 min under microwave irradiation to 160° C. The workup was performed by diluting the mixture with water and dichloromethane, extracting the aqueous layer twice and drying the combined organic layers over Na2SO4. The compound was 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 was isolated by evaporation of the solvent and chromatography on silica gel (dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-c43c9fc1c63a48e18fb83b92204f1dcf
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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